The Best Wedding Planners in Cheshire, MA

The Best Wedding Planners in Cheshire, MA

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139 Wedding Planners in Cheshire, MA

GemHidden gem
Only In My Dreams Events 

5.0

  • Offers 3 services
  • Starts at $3,000
  • Serves Cheshire, MA

We know that planning a wedding can be a daunting task! You’ve made the wonderful decision to declare your love in front of friends and family. Now the stress can begin. You’ll likely start asking yourself questions like: Where should we marry? What vendors do we need? Can we afford it? Who should we invite? How do we stick to a timeline? Never fear, after over 10 years of helping couples plan their dream weddings, we’re here for you. .Our wedding coordinator/planner extraordinaire Phil will be there to guide you from the start of your process until the end of your wonderful day.

Awarded Best of Zola
Oskar and his team are amazing. Smart, kind, organized. Fantastic experience. Strong planning and interpersonal skills. Really enjoyed working with them.
Jeffrey E., 2 years ago
Quick responder
Nene's Deco LLC 

5.0

  • Offers 4 services
  • Starts at $950
  • Serves Cheshire, MA

Decoration is my passion! Nene's Deco offers decorations services for all type of parties from wedding, to birthdays , baby shower, bridal showers, proposal, intimate decorations , baptism, corporate events, all milestones in your life or in the life of your business you will allow us to celebrate with you. We offer also event planning services, day of coordination, partial and full planning. We serving the Berkshires, Albany area, Springfield area , 50 miles radius from our location in Pittsfield MA. Choose your date and your theme, and we will take care of everything else. 💞

Nene and team were amazing. Amazing. I could write an entire book on how helpful they were before and during the wedding. Nene was our Day of Coordinator and helped us stay on track throughout the entire event. We put together a backyard wedding and Nene helped us to put together an entire schedule for the day. She became the point in contact of all of our vendors, and she helped control the flow of the crowd during this event. Where Nene shines is that everything I said Nene took control of unprompted. She never needed any direction and most of the time gave us ideas we did not initially think of. We were so lucky to have Nene on our side. She made our day special.
Chukwudi M., 2 years ago
GemHidden gem
Katie O' Weddings & Events 

5.0

  • Offers 7 services
  • Starts at $3,500
  • Serves Cheshire, MA

At Katie O’ Weddings & Events, our goal is to make every client sparkle. This means brighter smiles, louder laughs, and more excitement than you have ever experienced. Sparkling is about being fully immersed in the moment; it’s about being completely present, completely joyful, aware, and moved by all the positive energy and love surrounding you.

Katie and her team worked with us over nine months to ensure the wedding of our dreams was realized. They kept us on track with all the necessary, decision timelines, recommended our vendors, and visited a number of venues with us. Every minute of the day was orchestrated by the team flawlessly. One of the best moments was when they revealed the venue to us. It was magnificent. We cannot thank them enough.
Tracy M., 2 years ago
Quick responder
Effortless Events 

4.8

  • Offers 7 services
  • Starts at $1,000
  • Serves Cheshire, MA

Imagine walking into your wedding venue and being completely blown away by how perfectly every detail has come together. No stress, no worry - just pure joy and excitement for the celebration ahead.✨ At Effortless Events, we're dedicated to making that vision a reality. Our passion is to deliver unforgettable experiences that exceed your expectations, making your special day truly unforgettable. We believe that every wedding is more than just an event - it's a once-in-a-lifetime celebration of love, commitment, and happiness. That's why we're here to take care of every detail, from start to finish, so you can relax and enjoy every moment.

Awarded Best of Zola
From the moment I spoke to Madison, I just knew we were in the best hands. The last three months can be extra stressful leading up to the wedding and Madison and her team made me feel so at ease leading up to our big day. From coordinating with vendors on all the logistics, to the small details that I wouldn't have even thought of, Madison and her team always had it covered and handled everything with professionalism and always 5 steps ahead. They truly went above and beyond, allowing us to enjoy every moment without a single worry. And no ask was too small or large - we had to fully dismantle the venue the same night of and Madison and team took this off my plate which was a lifesaving moment! If you’re looking for a wedding planner who will treat your special day as if it were their own, look no further. Thank you, Madison & team!
Christina P., 9 months ago
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The Bailey Experience Wedding and Event Co 

4.3

  • Offers 5 services
  • Starts at $2,500
  • Serves Cheshire, MA
  • Offer

The Bailey Experience Wedding and Event Co. is a luxury wedding planning firm specializing in refined celebrations on land and at sea. Known for calm oversight and intentional execution, we curate wedding experiences that feel composed, elevated, and thoughtfully delivered. From cruise weddings to sophisticated celebrations throughout Washington, DC, Florida, and beyond, our work is defined by discretion, clarity, and seamless direction, allowing couples to be fully present throughout their celebration.

Awarded Best of Zola
We booked Teyanna in 2022 for our August 2024 wedding and did not regret it one bit. It was an absolute pleasure from start to finish. Teyanna was beyond accommodating and informative throughout the entire process. Her precise, creative, and professional "client-first" mentality shone through. From countless Zoom calls to meeting up in person to select flowers, it was more than we could have asked for and were expecting. Her professionalism and creativity showed through when we had to improvise our outdoor ceremony to an indoor one thanks to a horrific tropical storm. She called us on the morning of our wedding to ensure we were doing okay and went over every detail with both my husband and me to make sure she and her team didn't miss anything. We cannot wait to work with Teyanna again in the future.
Stephanie D., a year ago
Dhalia Events 

5.0

  • Offers 6 services
  • Starts at $3,600
  • Serves Cheshire, MA

Dhalia Events is an award winning event production company & was recently named "Best Planners in the Northeast" by LuxLife Magazine. Our magic is borne out of an insistence on creating bespoke, highly personalized experiences. We focus on the uniqueness of our couples by encouraging them to be their most authentic and raw selves. We've commissioned events for large brands such as Volvo Cars and worked with top tier social media influencers to plan their events. Our team has also worked regionally and internationally producing gatherings including destination weddings & corporate retreats. Our couples book us for the following reasons:

Awarded Best of Zola
Dhalia and her team were just amazing to work with! From our first conversation until execution, they were profession, kind and thorough. One of the best investments and decisions we made for our wedding day
Irene O., 2 years ago
Liv Charron Events 

5.0

  • Offers 3 services
  • Starts at $5,000
  • Serves Cheshire, MA

Hi there! My name is Liv and I am a New England born event planner. Being the youngest of 12 cousins, I went to my fair share of weddings growing up. I naturally fell in love with seeing the first chapter of my friends and families life begin. I’ve worked with some of the best vendors in the Seacoast, learning and growing as much as possible. In October 2021, I took a leap of faith and opened my own business! I'll never take for granted being able to work with clients I love, doing what I love. Let’s make your dream wedding a reality!

Awarded Best of Zola
It is not unusual for wedding planning to begin more than a year in advance of your big day. Venue, flowers, decor, churches (bring your own priest which is a thing), engagement photos, DJ, wedding party, save the dates, invitations. The list DOES. NOT. STOP. With all of these moving parts it really makes you wonder how such a complex event can happen without the slightest issue and seemingly end before you know it. Well, Liv is our reason. After months of planning, and picking, and choosing, and changing, and scrapping ideas our bandwidth for creativity and follow-through was wearing thin. Liv saved the day. She seamlessly coordinated communications between all parties and vendors to ensure that everyone was on the same page. I will honestly say that without her our day would not have come together like it did. Everyone tells you that something will inevitably go wrong regardless of how thorough your planning. Liv didn’t let that happen. The groomsmen forgot tie clips. Liv ran 5 blocks to pick up tie clips for the boys and was back before the girls even arrived at the church. Her foresight and planning were impressive but her ability to think and adjust on the fly is what made our day go off with zero issues. We cannot thank Liv enough for her help. Do yourself a favor and let Liv take it from here. Thank you again!!!
Kayla B., a year ago
Quick responder
Mills Memories 

5.0

  • Offers 4 services
  • Starts at $400
  • Serves Cheshire, MA

Justine Mills is the founder of Mills Memories, a full-service wedding company dedicated to creating unforgettable celebrations. With a deep passion for helping couples bring their unique vision to life, Justine blends creativity, organization, and an eye for detail in every event she plans. Known for her warm approach and dedication to stress-free, seamless weddings, she works closely with each couple to craft beautiful, personalized experiences. Justine’s commitment to excellence ensures that every wedding is not only stunning but also a joyful, meaningful day for all.

Awarded Best of Zola
From the moment I met Justine, I knew Mills Memories was an awesome wedding planner. She listened to the very creative couple on their ideas and helped plan each one to make it happen. The information she shared with me as a fellow vendor was a blessing! It was only the details that mattered, direct, to the point, no fluff, beautifully outlined and easy to understand. You want someone like her to focus on essential information without all the unnecessary distractions. I appreciate this, as it's completely different and better than most planners I've worked with. The quality of her work and dedication is truly high-end and professional. She went with the flow and kept the entire day running smoothly. I highly recommend Mills Memories!
Holly G., 5 months ago
Quick responder
Thyme & Details 

5.0

  • Offers 3 services
  • Starts at $3,500
  • Serves Cheshire, MA

Thyme & Details offers wedding planning and design services to sentimental couples looking for good vibes and premium personal touches. We know how important it is to be present in the moment – not worrying about organization, budgeting, managing vendors, etc. Let's make planning zesty so you can focus on your VIPs and enjoying your journey. We are based in Ohio but available for travel. Reach out so we can create something unforgettable!

Awarded Best of Zola
All couples need Dana and her team with Thyme & Details for their big day. We hired Dana as a day of coordinator but she is so much more than that. She went to countless vendor meeting and kept track of all of my overly detailed instructions to make sure each piece of our day (timeline, vendor contracts, etc) worked with those details. When the venue dropped the ball, others got details wrong, or vendors fell through, Dana was always a step ahead and came up with even better solutions than our original plans. Dana really knows the ins and outs of organizing a wedding, is in tune with the Columbus wedding scene, and has incredibly valuable connections. Overall we were blown away by Dana and her team’s professionalism and dedication to our wedding. Dana’s communications were always prompt, detailed, and thorough every step of the way, making the planning process a breeze. She lead our rehearsal too which is exactly what we needed. Her team also went above and beyond the day-of to ensure every aspect of our special day was executed flawlessly. We cannot recommend Dana and her team highly enough to any couple looking for a wedding planning team that will truly make their day unforgettable. Could not imagine our day without her!
Helen S., 2 months ago
Quick responder
Before You Say I Do 

5.0

  • Offers 5 services
  • Starts at $2,400
  • Serves Cheshire, MA

Hello, my lovely couples! My name is Annie and I have started my business at the beginning of 2023 and so far I've had clients from all over the East Coast. I am focused on Partial, Full time Wedding planning, Elopements and A-la carte. My goal is to help my clients and make sure that their wedding goes by the plan that they created.

Awarded Best of Zola
Annie with Before You Say I Do was the perfect wedding planner. Her communication style was punctual, organized, clear and consistent, providing much-needed emotional assistance and support throughout the planning process. She brought my vision for the wedding to life through her superior organizational skills, attention to detail, and hard work coordinating all my vendors and decor. On the big day itself, Annie made sure everything went smoothly, handling any issues with vendors gracefully and firmly so my husband and I could simply relax and enjoy ourselves. She truly went above and beyond, coordinating all aspects of the ceremony and reception so that not one person bothered us. Annie created an angelic wedding space that embodied my ideas and style. I could not have pulled off my dream wedding without her skill and emotional support every step of the way. Her services were worth every penny and I would enthusiastically recommend Before You Say I Do to any engaged couple looking for a wedding planner.
Christine Reeves B., 8 months ago
Quick responder
Rye Street Events 

5.0

  • Offers 3 services
  • Starts at $1,875
  • Serves Cheshire, MA

Rye Street Events was born from a deeply personal place: the joy she discovered while planning her own wedding! Inspired by the joy and creativity she found in bringing her special day to life, Caroline launched RSE with a mission: to turn each client’s unique vision into an unforgettable reality. With a strong unwavering commitment to excellence, Rye Street Events specializes in crafting one-of-a-kind experiences that leave lasting impressions. We are ready to bring your next celebration to life — and create memories you and your guests will cherish forever.

Awarded Best of Zola
Caroline executed our vision perfectly and I couldn't have made it through the day without her! She took my vision and made it an absolute dream. Every detail was perfect and it cut out so much unnecessary stress for me on our big day. She is so personable, creative, friendly, and reasonably priced and we couldn't be happier! Thank you for everything, Caroline! I would 100% recommend Rye Street Events for any of your coordinating, decorating, and planning needs.
Kelsey B., a year ago
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Wedding Planning Plus 

5.0

  • Offers 7 services
  • Starts at $2,500
  • Serves Cheshire, MA

The WPP Team is unlike any other wedding planning company in Upstate New York. Composed of a core group of four event planners, including the only in-house event designer in the area, WPP is able to care for their couples and bring their visions to reality from day one until the confetti hits the floor as the celebration ends. Add to that a talented group of dedicated event coordinators and Team WPP is able to build authentic event experiences and dazzle on wedding day like no one else can.

Wedding Planning Plus was an excellent choice for our wedding planning needs for our June 2025 wedding at the Equniox Resort in Manchester, VT. From the start, their communication style was direct, helpful, and calming, which was greatly appreciated as we planned our big day. The quality of their work and value they provided was outstanding - they were focused, supportive, and incredibly well-connected in the region, using their network of vendors to perfectly execute our wedding and beautifully and bringing our garden party tent reception vision to life. On the day of, Eliza ran the schedule effortlessly and her competence completely allowed my husband and I to be fully present. In particular, we appreciated the way that she approached us over the course of the wedding to check if we still wanted to do the next scheduled item, it gave us a sense of control over how we spent our time rather than feeling like we were manically running from task to task. So many of our friends and family have reported back that the wedding was the smoothest of the weddings they had attended this year, and its all thanks to WPP. We are so grateful for the incredible support Wedding Planning Plus provided and would highly recommend them to any couple planning their wedding.
Lydia S., 3 months ago
Quick responder
The Professional Maid of Honor 

5.0

  • Offers 4 services
  • Starts at $2,500
  • Serves Cheshire, MA

💍 The Professional Maid of Honor isn’t just a planning service—it’s your wedding day hype squad and backup bestie! Based in Boston and serving all of New England (Maine, New Hampshire, Vermont, Massachusetts, Rhode Island & Connecticut), we handle everything from dreamy invites to vendor wrangling with style, creativity, and a little extra sparkle. Whether you need full planning, partial support, or just someone to run the show on the big day, we’ve got you. Let’s ditch the stress and make your “I do” unforgettable!

Awarded Best of Zola
Katelynn made the planning of our wedding a pleasure. She was organized, always upbeat, has a great network, excellent ideas, yet not afraid to push back when needed. She kept the process moving along which allowed us to mostly enjoy the whole thing. She set us up for an amazing wedding, more beautiful than we could have even imagined. We loved working with her and recommend her wholeheartedly.
Elizabeth V., a year ago
GemHidden gem
Simply Loved Weddings 

5.0

  • Offers 4 services
  • Starts at $150
  • Serves Cheshire, MA

I'm Charissa owner & lead planner. My doormat says it best, 'running on coffee, wine, and the dog's time', but seriously I start every intro call with the disclaimer that you may hear the barking, snoring, or a squeaky toy in the background. I'm the twenty-something-year-old that's gone from throwing "Weddings" in her neighbor's driveway, to throwing them in some pretty amazing spaces. With over a decade of experience in weddings and corporate events, this isn't my first rodeo. Weddings are sort of my thing!

Awarded Best of Zola
Simply Loved Weddings was an absolute pleasure to work with for our wedding. From the moment we met Charissa, we were impressed by her calm, direct, and easygoing communication style. She truly listened to our vision and was able to elevate it through her organized, efficient, and trustworthy approach. Charissa went above and beyond, checking in with us multiple times to ensure everything was running smoothly. On the day of, we were able to simply enjoy ourselves, confident that Charissa and her team had everything under control. As far as we know, the entire event went off without a hitch, thanks to their incredible coordination and delegation skills. We cannot recommend Simply Loved Weddings highly enough!
Anne-Levert, a year ago
Quick responder
The Traveling Tee Events 

5.0

  • Offers 4 services
  • Starts at $3,500
  • Serves Cheshire, MA

Curating timeless memories with the beauty God gave us. Sustainably-focused, intentional design for intimate experiences. We offer full planning and design, month of coordination plus, and content creation through our Moments by The Traveling Tee Events division.

Having Steph & Mali coordinate my wedding allowed me to be present in every way possible. I can tell you every song that played and every single song I missed at my wedding. If I missed a song, it was because it was time to cut the cake or do the garter toss. In fact, the morning of my wedding, I was laying on the couch with my bridesmaids and a facemask until 10am. How many brides can say that? We hired Steph because I knew I couldn't do it all myself (wrangling together our Mexican and American families). She went out of her way to recommend our DJ and cake and absolutely knocked it out of the ballpark. She toured our venue and befriended all of the staff which made vendor coordination meetings go smooth. Although our venue came with a coordinator, I felt that I needed someone who knew what I wanted and would voice that to others. Steph was that mind reader. Steph and Mali are your people from the moment you wake up on your wedding day. We asked them to help with set up, timeline, and break down. I have no idea how they managed to set up our venue up to pure perfection and also make sure either Mali or Steph was with the bride/ groom at all times. At one point, Mali noticed we were struggling with our dog and offered to hold her leash while we finished up with family portraits. I can't tell you if anything went wrong because Steph just handled it. Day of, I was asked about 4 questions and if any changes needed to be made, Steph made sure I approved them, even if my mom said it was okay hahah. Steph is always prepared for worst case scenario. She helped me out with providing like 20 batteries for these inflatable sharks I was using on the dance floor. Which without the inflatable "Bad Bunny" sharks, my dance floor would not have been as awesome. She also offered me some liquid IV for when my legs started to cramp up from all the dancing I was doing. Day of coordinator is not enough of a title for what Steph does. She's so much more and I'll never be able to thank her enough.
Clara M., 2 years ago
Quick responder
MB Events 

5.0

  • Offers 3 services
  • Starts at $3,000
  • Serves Cheshire, MA

Here at MB Events, our number one goal has always been to have happy clients. From helping them plan at a pace that works for them, to keeping everything organized and stress free. We truly value the friendships that are made throughout the process.

Awarded Best of Zola
My husband, Chris, and I were fortunate enough to book with MB Events almost two years out from our wedding date of July 19, 2025. We love telling everyone that working with Marissa was the 2nd best decision we made (other than marrying each other, of course!!) Throughout the inevitable chaos of wedding planning, Marissa was our rock. She kept us on track with timelines and payments, managed communication with nearly 10 vendors at once, and helped bring our entire wedding vision to life. She truly has “the eye” — something Chris and I lack — making her guidance that much more invaluable when crafting our mood board and creating the overall design for wedding day. Her dedication, hard work and care never went unnoticed and we even had guests come up to us that night saying how amazing her team is! Every hiccup was handled with grace and professionalism, allowing our day to run as smoothly as possible (and it did!) If you choose to hire Marissa, just know you are not just hiring a planner but also gaining a friend and member of the family. Working with her over the last two years has been a blessing and more, and we owe so much of the joy we felt on wedding day to her. THANK YOU Marissa and MB events! We love you!
Ellie M., 4 months ago
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Avenue Design Studio - Planning & Rentals 

5.0

  • Offers 6 services
  • Starts at $250
  • Serves Cheshire, MA

At Avenue Design Studio, we began as a floral business, but quickly realized we could offer so much more to our clients. Over our 10+ years of working with couples on those special lifetime moments, we found ourselves stepping in to assist our brides and event clients with planning, vendor coordination, and overall event management. This inspired us to shift our focus and create Avenue Design Studio, a full-service event planning and design company. Whether you’re looking for full-service planning or just need assistance with specific aspects, we provide multiple packages and a la carte options to fit your needs. You dream it, we create it.

You made my day incredible. I had a vision and Chad blew it out of the water. I walked into the reception before our happy hour started and my mouth dropped. Stunning. I had no stress at all on my wedding day and he handled any issues that arose beautifully. I cannot say thank you enough for ensuring my day was more than I even imagined.
Jenna G., a year ago
Quick responder
Idyllwild Event Design 

5.0

  • Offers 3 services
  • Starts at $7,500
  • Serves Cheshire, MA

Idyllwild is an event design company for revolutionary spirits. We create laid-back and luxurious mountain love parties for New York's most passionate people. Idyllwild serves the Hudson Valley, south-central and eastern Catskills, and Western Berkshires, and functions in a hybrid online/in-person capacity. In addition to helping you plan all the visual aspects of your event, we offer floral design service, vendor and rental recommendations, sourced and custom-built decor and signage, and vintage accent furnishings. If your style is timeless as it is eclectic, rooted in Nature, beauty, and community, Idyllwild is for you!

Some people might have a detailed vision for what they imagine on their Wedding day. I was not one of those people! I had a vague sense of wanting something ethereal and dreamy, with no clear direction of getting there. But from my very first conversation with Jasmine, I had full trust in her creative abilities and eye. She took the reins and crafted something far beyond what I could have ever dreamed up. The arrangements were just breathtaking-lush, romantic, and the arch (!!!!!) she built by hand was so elegant, intricate, and complimented our outdoor venue perfectly. What really stood out, however, was the way she went above and beyond. She picked up so much of my slack with grace and consideration and helped in every way she could. Our wedding flowers and design are some of my favorite parts of our wedding and we will forever be so thankful for all that she did for us. I highly recommend Jasmine to any couple looking for a beyond talented, thoughtful, and incredibly reliable vendor. Be prepared to love her! Book her immediately!!!
Emma & T., a year ago
A Lively Event 

5.0

  • Offers 4 services
  • Starts at $3,150
  • Serves Cheshire, MA

At ​A Lively Event, we specialize in thoughtful, detail-driven wedding planning for couples. Our focus is simple: bringing your unique wedding vision to life while building a genuine relationship with you every step of the way. We believe that planning your wedding should be just as joyful as the day itself. We prioritize communication, trust, and collaboration. Whether you’re dreaming of a romantic mountain ceremony or an elegant ballroom celebration, our team is here to guide you with expert logistics, creative solutions, and unwavering support. We handle the behind-the-scenes details so you can stay present and excited for your big day.

From the very first phone call with Katie with A Lively Event, I knew she was meant to be in our lives. We instantly clicked. Hiring her felt less like choosing a wedding planner and more like gaining a built-in best friend who also happens to be a logistics genius and life-saving personal assistant all wrapped in one. Katie has a remarkable gift for bringing every vision together seamlessly, even when there are many voices, ideas, and passionate opinions swirling in the mix. Every detail was handled with care, every question answered before I even had to ask. If anything went sideways (and let’s be real, there’s always something), she swooped in with grace and handled it before I even realized there was an issue. I never once had to stress or lift a finger. She was our voice, our advocate, and the one person who always ensured our wishes were front and center, and truly was the key to how perfect our wedding day turned out to be. Thanks to Katie, those few precious hours of our wedding day became some of the most unforgettable memories of our lives. Her heart, her hustle, and her unwavering support made every moment perfect. We are forever grateful to have worked with her, and even more grateful that she’s now a part of our life beyond the wedding. If you want someone who will champion your love story with joy and finesse, Katie is the one.
Jessica P., 2 months ago
Events by Wei Yuh 

5.0

  • Offers 4 services
  • Starts at $3,500
  • Serves Cheshire, MA

As an event planner with over a decade of experience, I've had the privilege of helping countless couples create unforgettable celebrations. My passion lies in crafting personalized events that reflect your unique love story. From intimate ceremonies to grand receptions, I'm dedicated to ensuring every detail is perfect.

Awarded Best of Zola
Wei Yuh was hired for the task of organizing a lovely and elegant Victorian Romance themed wedding rehearsal dinner at the Omni Parker Hotel on October 24, 2025. Following the dinner, a private Ghost Tour of Boston also took place for the wedding party, and the timing for these events was crucial. She did so professionally, with good communication with myself, the hotel staff, and the florist. From lace table runners to floating candles, everything was perfect when we arrived. Wei Yuh also communicated well with our guests concerning the day’s itinerary, suggestions for appropriate dress (since the ghost tour could be a bit chilly), and handled special needs requests with ease. She took charge of scheduling gift presentations and toasts between courses, tweaking them as needed to meet our schedule. I couldn't be happier with her services and I appreciate the work she put forth to make this event a very special evening!
Nancy D., a month ago
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Yours Truly Planning 

5.0

  • Offers 7 services
  • Starts at $1,000
  • Serves Cheshire, MA

***CLICK ON GLOBE ICON UNDER PROFILE PHOTO TO FILL OUT WEDDING INQUIRY FORM. WE WILL ONLY RESPOND VIA BY FORM.*** If you would like us to get start on planning directly, we ask that you kindly fill out the form and one of our team members will get back to you as soon as possible!

Awarded Best of Zola
Truly Planning made our big day less stressful. The venue they picked was overlooking the ocean & all the other vendors picked were spectacular! Will hire them again for another event ours!
Chloe, a year ago
Quick responder
Charity Lynn Weddings 

5.0

  • Offers 1 service
  • Starts at $11,000
  • Serves Cheshire, MA

Through intentional design and meticulous planning, I craft a wedding experience that reflects your unique essence, infused with awe-inspiring details. Because your love story is the most extraordinary of all, I strive to create an experience that encapsulates the elements that make you special while meticulously attending to every logistical detail. Imagine a harmonious blend of beauty in the details and a spirit of epic celebration. I am passionate about creating authentic and thoughtfully designed weddings for couples who cherish their families.

Awarded Best of Zola
Charity Lynn wedding planner is easy and fun to work with. She was excited for our event together, worked tirelessly around the clock to bring the vision to life, and provided support to every vendor. She meticulously crafted every detail; no matter how big or small. Her emergency kit is filled with every last item you may need. Highly recommend her services!
Alyssa black , 2 years ago
Quick responder
The Perfect Plan 

5.0

  • Offers 4 services
  • Starts at $3,500
  • Serves Cheshire, MA
  • Offer

The Perfect Plan was born from a deep-seated belief that every couple deserves to experience the joy of their engagement without the stress of wedding planning. Our founder, Connie Nye Clark, spent two decades immersed in the hospitality industry, mastering the art of event execution and building a robust network of trusted vendor relationships. She saw firsthand the difference a seamless, expertly planned event makes—not just for the guests, but for the couple themselves. We exist to guide you through every decision, big or small, ensuring your journey to "I do" is as beautiful and stress-free as the day itself.

From the moment my husband and I booked The Perfect Plan as our wedding planners, we were impressed by their quick responsiveness and the wealth of information they provided. Connie and her team were incredibly knowledgeable, with a great attention to detail that allowed them to think ahead and ensure our special day ran smoothly from start to finish. Connie's upbeat and excited personality was a calming presence throughout the day, keeping me feeling calm and joyful. We are so grateful to The Perfect Plan for making our wedding day everything we dreamed it would be and more. Their professionalism and dedication truly made all the difference.
Danielle, 3 months ago
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West Monroe Events 

5.0

  • Offers 6 services
  • Starts at $1,500
  • Serves Cheshire, MA

Welcome to West Monroe Events – Your go-to for unforgettable weddings. Serving cities like Austin, Boston, and San Diego. We specialize in crafting beautiful, personalized weddings. Our expert team is dedicated to turning your dream day into a reality, handling every detail with care and precision. From intimate ceremonies to grand celebrations, we ensure your special day reflects your unique love story. Contact us today to start planning a wedding that you'll cherish forever.

Can’t recommend Amanda enough! She went above and beyond for our wedding day. She tackled any issue that came up had such a calming presence for us. They also handled decorations that turned out better than even I planned! As a type-A bride, I felt so comfortable giving her the reigns. Everything came out perfect and beautiful!!
Payton D., 9 months ago
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Louisa Co. Events 

5.0

  • Offers 4 services
  • Starts at $1,400
  • Serves Cheshire, MA

At Louisa Co. Events, we create weddings that feel effortless, elegant, and deeply meaningful, blending timeless style with modern sophistication. With over 10 years of experience across New England, trusted vendor relationships, and a calm, creative approach, I ensure that every moment is beautifully orchestrated and every detail perfectly aligned.

My husband and I had the most amazing experience working with Jamie. We only had a 3 month engagement, so it was crunch time pretty much the entire time we were planning. We hired Jamie 2 months prior to the wedding, and she made everything so stress free. Anything we asked of her, she was more than happy to do, and if she didn’t have the answer right away, she would find out and get back to us in a very timely manner. I did all the decorating myself, and Jamie had some great ideas to help me execute my day. While she kept things professional, she also felt like a friend. Her kind spirit and go getter attitude was so great to have on the day of our wedding. She handled EVERYTHING the day of the wedding and everything ran so smoothly. Everything that needed to be done the day of was in the perfect spot just where I asked her to put things, and she ran the event flawlessly. She was in contact with all my vendors and she worked out all the details with them so I wouldn’t have to which was the biggest help. My husband and I did not know what to expect going into planning, but Jamie and her team exceeded our expectations. If you are looking for someone to help you plan your wedding, I would say stop looking you have found your girl. Jamie’s assistant was also amazing and just as pleasant. I highly recommend working with Jamie and her team, and I would 100% hire her again for another event. Best experience
Kendra, 7 days ago
GemHidden gem
unKAGed events 

5.0

  • Offers 7 services
  • Starts at $1,400
  • Serves Cheshire, MA

While planning events as a side hustle for over a decade, I have also been a nonprofit event coordinator, farmer, and music festival planner. My background gives me a unique perspective on each wedding I plan. Sustainability, Inclusivity and Couple Advocacy are extremely important to me. Some fun facts: Leo with Taurus Moon and Libra Rising, ENFP, a Peacemaker, and I love a good personality quiz. I'm a sucker for fashion, and like to joke that ! can smell a good consignment/vintage shop. I had a wedding Pinterest 8 years before I even met my husband, and I will do anything in my power to give you the wedding you want.

Awarded Best of Zola
Kris was wonderful to work with start to finish. Based off the size of our families, we were initially struggling with the daunting task of navigating a large scale wedding while still making sure our number one priority of efficiency, seamlessness, and intentionality were maintained. We expressed these concerns to Kris early on and were met with understanding and confident guidance towards practical solutions. Kris knows the Hudson Valley very well. Working with someone who lives here and knows this areawas very important. Seeing Kris spring into action day of the wedding was wonderful. She was calm and collected but simultaneously leading the charge and making everything happen - we had not a worry in the world for the whole day and we are very thankful for that.
Benjamin L., a year ago
GemHidden gem
Lovelace Design 

5.0

  • Offers 5 services
  • Starts at $7,000
  • Serves Cheshire, MA

NOTE: Please email us directly if interested in working together... At Lovelace Design, we believe that planning your wedding should be a journey filled with moments of joy and connection. We specialize in designing events that are both sophisticated and intentional, so that you can savor every moment of your special day. We offer comprehensive event planning services for busy professionals that don’t have the time to plan every detail leading up to their big day. Our team of experienced planners will work closely with you to ensure that your wedding is truly unique and reflective of who you are.

Awarded Best of Zola
We can’t imagine our wedding day and planning process without Christina—we hired her for wedding coordination and are SO glad we did! From our first conversation with her to our hugs goodbye on the wedding night, Christina was warm, fun, and professional. She kept us and our vendors organized with regular touch points over email and Zoom in the months leading up to the wedding, giving us her professional opinion on ways to make the day flow and feel the way we wanted. During our rehearsal and wedding day Christina was organized, clear, detail-oriented and friendly to everyone involved and we knew our day was in the best hands with her. We were able to be completely present and soak in every moment because Christina and her team were working in the background to keep us on time and problem solving on the fly. If there is one thing you do for your wedding, hire a coordinator—specifically, hire Christina—you’ll be glad you did!
Sara, 2 months ago
GemHidden gem
Cathy's Elegant Events, LLC 

5.0

  • Offers 4 services
  • Starts at $9,000
  • Serves Cheshire, MA

Cathy founded Cathy's Elegant Events in 2010. Although she was born in NYC, her family moved to the Catskill Mountains at a young age, but they maintained a home in Brooklyn. This allowed her to have a unique upbringing in both Upstate New York and Brooklyn, where many of her relatives still reside. Cathy holds a degree in Mathematics and Statistics.

It was so fun getting to spend time with her and getting to know her during this process. Cathy made every little detail of our fairytale wedding come true. She was terrific during the planning process. When I wanted to try to handle projects myself, she stepped back and let me handle them, but was always there if I needed advice or help with anything. When I needed her to be more involved and hands on, I felt completely confident and comfortable letting her take things in the direction that she felt was best. She was always quick to answer emails and talk on the phone to hash out big picture items or last minute details. The week leading up to the wedding Cathy was AMAZING. We spent almost 2 hours on the phone making sure every last detail was taken care of and exactly the way I envisioned it. She ran our ceremony in the pouring rain and was always cheerful and positive, she was there for me for moral support all afternoon while I was getting ready, she helped setup the barn and ceremony beautifully and made sure every detail was in order. During the ceremony and reception, she made sure that my husband and I were taken care of the entire evening. Our day was absolutely perfect from start to finish and Cathy's expertise, guidance and help played such a huge part in the success of our wedding day. Thank you Cathy!! Tim and I are so grateful for all the hardwork and love you put into making our day great.
Elise D., a year ago
Eileen Smith Events 

5.0

  • Offers 5 services
  • Serves Cheshire, MA

Her experience, creativity & knowledge in the event industry puts her ahead of most in the area. She loves creating and working with clients on all levels to make their vision become a reality. "I love getting to know my clients and enjoy becoming their "New Best Friend" prior to the event.". Her talent in design, organization, and management makes any experience working with her effortless. She makes you feel so comfortable & give you the confidence it will be an amazing event.

Eileen was amazing as our wedding planner / month-of coordinator. Both my husband and I were SO glad we hired her. Eileen helped us make so many decisions during the planning process that led to an extremely smooth wedding day - from where the bar was located to how we processed down the aisle, from whether to do cake or a dessert bar, to when champagne was poured - she really nailed it. She also worked with all of our vendors to coordinate setup and was onsite to help make sure everything was set up correctly & as planned. Everyone jokes that something *always* goes wrong on your wedding day, no matter how much you plan, but really we had nothing go wrong thanks to Eileen! She made our day stress-free! It's also important to call out that our venue wedding coordinator quit a couple of weeks before our wedding, and Eileen stepped up and swooped in to make sure our new point of contact at the venue was fully up-to-speed. Thank god for Eileen! I highly recommend her. And if you're on the fence about needing a wedding coordinator -- just take the leap! SO SO worth it.
Claire M., a year ago
Quick responder
Allure Affair 

5.0

  • Offers 5 services
  • Starts at $500
  • Serves Cheshire, MA

At Allure Affair, we specialize in creating luxurious, beautifully curated weddings and events. Whether you're planning a grand celebration or an intimate elopement, we bring your vision to life with creativity, precision, and seamless execution. Our services include full-service planning, event design, and day-of coordination, ensuring a stress-free and unforgettable experience. For couples seeking select assistance, our à la carte services provide customized support tailored to your needs. From sourcing stunning venues to collaborating with top-tier vendors, we handle every detail with care and expertise.

Allure Affair was an absolute delight to work with for my best friend’s birthday celebration. Their prompt and efficient communication eased the stress of planning, ensuring every query was addressed with care. Their professionalism was matched by their ability to seamlessly incorporate our personal vision into the event, making it feel uniquely ours. Despite working within a limited budget, they went above and beyond, creatively utilizing existing décor to maximize impact without compromising elegance. Their meticulous attention to detail and dedication truly elevated the occasion, leaving us thoroughly impressed. Worth every penny—without a doubt, we would love to collaborate with Allure Affair again for future events.
Sri L., 10 months ago

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