Real Wedding: Kelsey & Will

An elevated backyard wedding in Massachusetts

Beautiful Backyard Wedding in Massachusetts | End-of-Summer Wedding Under the Tent

A wonderful wedding surrounded by nature and filled with only the warmest memories and feelings — such was the celebration of love for Kelsey and Will at their lovely end-of-summer backyard wedding in late August. Wildflowers, elegance and sincerity, lots of fun and a reception under the tent — read on to find more details about this amazing event.

Tell us a little about yourselves. How did you meet? What do you do for a living? What are your hobbies?

Will and I found each other on the internet in 2017! On our first date, we went for drinks at a cocktail bar in Williamsburg followed by a New Orleans brass band concert. By the third date, Will invited me to his cousin's birthday party (who officiated our wedding), and by the fourth he asked me to come home with him for Christmas, and the rest is history. Will is the principal of two charter schools in Manhattan and I work in supply chain for a hair care brand called Crown Affair. Over the last year or so, we've grown to love running — we did a couple of half marathons last year, and are currently training for a half in the spring, followed by the NYC marathon in the fall. We live in Brooklyn, NY with our dog, Nellie, and start most weekends with a run followed by a trip to the dog park.

Can you share your engagement story?

We got engaged in May 2022 on the beach in North Carolina. When Will suggested we spend Memorial Day weekend at my family's beach house, my suspicions of an engagement grew. My family's home at the beach has always been my happy place. When the world shut down in 2020, Will and I headed south from NYC and spent over 6 months down in North Carolina with my parents and five siblings. It became a very special place for the two of us — as we embraced a slower pace of living and the sunshine. We landed Memorial Day weekend and went for a late afternoon walk along the ocean, something we've always enjoyed, and Will popped the question a few minutes into the walk. He had a photographer out on the beach to capture the moment — we jumped and cried, it was so special. When we returned to my parent's house, my whole family was on the porch blasting music, jumping up and down, ready to celebrate — it was one of the best nights of our lives.

Did you have any pre-wedding events, like a rehearsal dinner or bridal shower?

We had our rehearsal dinner in Will's parent's backyard. It was a perfect, intimate, dinner party with our closest family and friends. To save a little bit of money, I chose to design and create the tablescape myself. We used locally grown flowers from a flower farmer neighbor, placed in vintage ink pots as bud vases that I sourced from UK-based Etsy sellers. I was dead set on having fruit-covered tables, so we spent the morning visiting every farmstand and grocery store in town to pick up all kinds of tomatoes and other fruits to style with. My sisters tagged along, and it was fun to spend time together before the craziness of the weekend began. Will's mom and I collaborated on all of the logistics, I couldn't have done it without her! It all came together beautifully with toasts from our loved ones and a family-style meal, many Aperol spritzes, followed by dessert. Following the rehearsal dinner, we hosted welcome drinks at a local winery for all guests coming from out of town. It was happy, low-key, and great to spend some quality time with the people we were going to celebrate with on Saturday.

Where was your wedding? Why did you choose this venue?

Our wedding was at The Inn at Kenmore Hall in Richmond, Massachusetts. It's an old historic house that a couple renovated and opened as a bed & breakfast. I always pictured our day as an elevated backyard wedding, but city living doesn't lend itself to a yard. I began the venue search in the Catskills but didn't quite connect with any of the venues I came across. Will's parents had recently bought a home in the Berkshires, so I decided to extend the search there and came across The Inn at Kenmore Hall. I was immediately drawn to the home's stunning, expansive backyard and fell in love with the perfectly curated yet lived-in interior. Frank and Scott, the owners, have done an incredible job remodeling every inch of the home and property to feel warm, elegant, and perfectly imperfect. When I Google-mapped the Kenmore's distance from Will's parent's home, I learned it was less than a mile down the road, it was fate!

What was the concept behind your wedding and how did you find your inspiration?

We wanted our day to feel true to us and felt strongly that it didn't feel stuffy or overly formal. Our wedding was at the end of August, so we wanted an end-of-summer soireé vibe, pulled together with a celebration of our love and an epic party. The month after we got engaged we took a trip to Italy — we spent time in Ischia and Puglia. I fell in love with the abundance of moss-covered terracotta pots, the overgrown flowers, and al fresco dining. In the beginning, I pulled a lot of the design inspiration from our European adventure. As we spent more time in the Berkshires and around the Kenmore, we got to know the landscape of the area and felt like we could lean more into the upstate, overgrown wildflower, natural beauty vibe with hints of Italian summer. Richmond is a super casual, low-key town, so we didn't want to stray too far from that. We both have pretty rambunctious families and friends, so the relaxed nature of the day allowed them to let loose and have fun which is all we could ask for!

How long did it take to plan your wedding? Did you encounter any challenges during the planning process?

It took just under a year to plan the wedding. I mostly found planning to be fun and loved the creative side of it, but there were moments when I felt unsure of the process. At times I found myself questioning — What am I forgetting? Am I making this decision too late? Are we spending too much money on this one day? Which can be unsettling, but it seems to all come together in the end. Our planners were super helpful and crushed the day of! I am forever grateful for their work throughout it all.

How many guests did you have? And what was the seating arrangement at the wedding like?

We ended up with around 120 guests, and I was set on long banquet dinner tables. We placed two long tables on either side of the dance floor and bar. Will and I sat amongst our siblings and closest friends, which we loved because it felt like we were a part of the party and experiencing the day alongside the people we love the most. We provided assigned seats and our parents sat across the way facing us. It was so special to look over and see them laughing and enjoying dinner with one another.

Tell us about your outfits. How many different styles have you tried?

I love fashion, and I often found myself dreaming about what I would one day wear for my wedding, but when the time came to search for a dress I found the experience of deciding to be incredibly overwhelming! My first stop was Danielle Frankel, whose dresses are unbelievably stunning, but I didn't think I'd end up wearing one. I was pleasantly surprised when I left the first appointment narrowed down between two dresses. After visiting a couple of other designers, nothing compared to the two gowns I had my eye on. When I returned to Danielle Frankel for a second appointment, I landed on the Leona gown. It was most important to me that I felt physically comfortable and the most like myself in whatever I wore, and the Leona was perfect. It was an off-the-shoulder gown, with a square neckline and a tulle overlay that was gathered at the top of each sleeve. I loved how simple it was with the tulle adding a little something extra. Truthfully, I never felt that connected to being a "bride", and a veil felt a little too bridal for me, so I opted to go without one. When the day came, I felt like I had chosen the dress I was meant to wear, which was the goal all along! I kept the jewelry simple with diamond studs I borrowed from Will's sister and a dainty gold necklace with a ruby pendant that was passed down to me by my grandma. Will wore a deep navy tux from Suit Supply, and looked so handsome. For the rehearsal dinner, I knew I didn't want to wear white. I came across this fuchsia, silk, halter-neck gown by Azeeza on Poshmark and fell in love with it! Our rehearsal dinner was in Will's parent's backyard and I liked the idea of the fuschia dress against the green grass. I paired the gown with olive green Staud mules, and simple hoop pearl earrings by Jennifer Behr. Will wore an off-white checked blazer with off-white pants from Suit Supply and white sneakers.

What was your first dance song? Did you choreograph or improvise?

Our first dance song was 'These Ain't Raindrops' by James Carr. It may sound like a sad song, but it's a happy one for us — we fell in love listening and dancing to that song in 2017 in Will's apartment, so it felt like a no-brainer to be the choice for our first dance. Will's sister is a professional dancer, she came over about a week before the wedding and taught us a few moves. We aren't natural dancers, so it was perfect to have Jane help us out.

What was the most memorable moment from your wedding day?

It is so hard to choose just one moment! We didn't go for the traditional — groom sleeps away from the bride the night before, so we woke up together in our room at the Kenmore. The morning of the wedding we had the most lovely, quiet breakfast together in our room. We were excited, nervous, and curious about what the day had in store. I'm a more anxious person, and having that breakfast together before the whirlwind of the day was perfect to calm our nervous jitters. Following breakfast we went our separate ways to get ready — I stayed at the Kenmore and Will headed to his parent's home. I decided to do my own hair and makeup for the day, which may sound crazy, but it took the pressure off not having a rigid hair and makeup schedule that morning. It allowed Will and I to spend the early morning together, and made getting ready feel more intimate with just my mom, sisters, my best friend, and sisters-in-law. All of us crammed in one bathroom together with music playing — it was a highlight. For our ceremony, we opted to write our vows. We laughed and cried through them, which was slightly embarrassing but all in all incredibly special to let our guests in on our love story. Whenever someone would ask us how planning was going leading up to the wedding we would usually respond something like, "We just want it to be the best party ever", I'm biased but I think we did just that! We had a dance set before sitting down for dinner, and it amped up the energy under the tent. It truly felt like everyone was letting loose, having the time of their life. As cliché as it is, the feeling of everyone you love the most surrounding you in one place is unforgettable.

Are there any vendors that you would like to tell us a little more about?

By the end of the weekend, we were completely obsessed with our photographer, Kayla Snell. She was calming, organized, and an overall lovely human to be around. She made us feel comfortable and went above and beyond when shooting our day. She floated through the day with ease, and we were blown away when we received our album. Her partner shot Super8 film for us as a last-minute addition and we will cherish the photos and video forever, they both captured our day to perfection. I truly could not have asked for a better photographer for our rehearsal dinner and wedding day and we feel so grateful to have had the opportunity to work with her! Our florist, Lindsey from Fern & Fawn Flora was amazing as well — she exceeded my expectations and brought my wispy wildflower dreams to life using seasonal blooms. She's incredibly kind, laid back, and easy to work with. And Kate, our caterer, also a neighbor to Will's parents - was the best! Wedding food can often be unremarkable, but Kate and her team cooked up a delicious, fresh, summer menu for our day. Our DJ, Cole, took our set-list direction, ran with it, and kept everyone on the dance floor the whole night. We were lucky to work with so many amazing vendors. Truly everyone was top-notch.

Did you have any special or unique elements (such as a signature cocktail or a fragrance) at your wedding?

I found the design aspect of wedding planning an amazing creative outlet for me. I've always been interested in calligraphy and design (I took a calligraphy class back in 2018!), so I decided to take on the creation of our menus, both the dinner menu and cocktail menus for the bars, along with some other small signage. It was special to create something that would be a part of each guest's experience, and I loved the process — something I hope to continue! As a nod to the Italian summer we served Aperol spritzes with Castelvetrano olives as the garnish during the cocktail hour. We hosted the after party back at Will's parent's house, complete with an absurd amount of McDonald's — it was a hit and I highly recommend it to all!

What advice would you give to couples who are currently planning their wedding?

Spend some time before booking your venue to land on your overall vision for the day, focusing on how you want it to feel before landing on what you want it to look like. I found that refining the vision was grounding throughout the process when it came to seeking the right vendors and choosing design elements. I was able to have more productive conversations with potential vendors because I was so clear on what my aesthetic was, and how I wanted our guests to feel. I would also say don't get too caught up in wedding trends, or what other people are doing at their wedding. Tune out the noise and stick with what feels natural for you and your partner across all aspects of the day — from what you wear, to the design, the music, the timeline for the day, all of it. If you do, it will all come together perfectly. Little things may not go your way, and it can all be overwhelming at times, but be sure to remind yourself to take a step back and lean into what truly matters - the celebration of your love! Oh, and the couple sets the tone, so if you want a party you have to be out there partying.