Jackie and Trent’s Willowdale Estate wedding paired classic New England style with plenty of personal details. White florals, greenery, and candlelight complemented the estate’s historic stone architecture, while a handmade “Please Be Seeded” seating chart, wildflower seed favors, custom playing cards, and matching Christian Louboutin shoes added touches that were distinctly theirs.

The setting also made sense for a couple whose story began in Boston. Trent had moved there from Virginia just a month before meeting Jackie at a neighborhood dive bar, despite his mom jokingly warning him, “Whatever you do, don’t move to Boston and find a Boston girl.” Years later, friends and family from both places came together for a weekend that started on the North Shore and ended with a packed dance floor.

What We Love About This Willowdale Estate Wedding

• A handmade “Please Be Seeded” seating chart paired with packets of wildflower seeds for guests to plant at home
• Private vows read before the ceremony so Jackie and Trent could connect without doing a first look
• Matching Christian Louboutin shoes and hidden messages incorporated into their wedding-day attire
• Custom playing cards that doubled as a guest book
• A surprise original song performed by Trent’s dad during the ceremony

Bringing Boston and Virginia Together for a New England Wedding

Jackie and Trent met at Murphy’s Law, a Boston neighborhood dive bar, only a month after Trent had moved from Virginia. Mutual friends introduced them, they hit it off, and then Trent left without getting Jackie’s number. Jackie solved that problem herself by messaging him on Instagram the next day. Their first date followed, and later, over pizza at Regina Pizzeria in the North End, Trent asked her to be his girlfriend.

Boston became part of the relationship almost by default, but their wedding also needed to make room for where Trent came from. When they toured Junebug venue vendor Willowdale Estate, both of them started crying. “It was the only venue that gave us that feeling, because it perfectly captured who we are as a couple: a beautiful blend of my Boston roots and Trent’s Virginia upbringing,” Jackie says.

They extended that sense of place beyond the wedding day. The weekend began with a rehearsal dinner at Riversbend in Essex, overlooking the marina and close to Gloucester, where Jackie and Trent spend their summers. After dinner, they opened the celebration to everyone with a welcome party, giving friends and relatives arriving from Virginia and elsewhere a taste of the North Shore before the main event.

Hiring Vendors Familiar With the Venue Made Planning Easier

Most of the couple’s vendors came from Willowdale Estate’s preferred vendor list, a practical decision that became increasingly useful as planning progressed. That familiarity meant the team understood the flow of the venue, knew where different parts of the day worked best, and could make recommendations based on previous weddings there.

About 12 weeks before the wedding, the venue paired Jackie and Trent with event coordinator Julia. For a bride accustomed to keeping track of everything herself, handing over the day-of logistics could have been difficult. Instead, Jackie says Julia made it possible for her to stop thinking about what was happening behind the scenes. “If there were any surprises or challenges, I never knew about them, and I think that’s the greatest compliment we could give our team,” she says.

Saving The Biggest Ceremony Surprise For The Guests And The Couple

Because Jackie and Trent had saved their first look for the aisle, the ceremony carried a moment they had deliberately protected all day. Their pastor told the story of how they met and how their relationship developed, but another part of the ceremony came as a surprise to both of them. Trent’s dad had written a song for the couple and performed it during the service. “There truly wasn’t a dry eye in the room,” Jackie remembers.

It also fit naturally into a wedding where family had been involved well beyond simply attending. Jackie’s mom had essentially become her unofficial planner. Her stepdad built one of the reception’s most recognizable pieces. Trent’s dad added something to the ceremony that couldn’t have been ordered from a vendor.

Adding Private Details to Their Wedding-Day Fashion

Jackie wore two bridal looks, beginning with a classic ceremony gown before changing into a reception dress with a statement bow that gave her more freedom for dancing.

Her bridesmaids wore different dress silhouettes in the same sage green floral print, while the groomsmen stayed with black tuxedos. Jackie paired a sleek low bun with soft makeup rather than changing her appearance dramatically for the day.

Some of the couple’s favorite fashion details were considerably less obvious. Jackie and Trent wore matching Christian Louboutin shoes, while the inside of Trent’s custom tuxedo carried a message embroidered for him by Jackie. They also engraved private messages inside each other’s wedding bands.

Featured Vendor:
Willowdale Estate

Putting the Wedding Budget Toward Food, Music, and Photography

When Jackie and Trent decided where to put their budget, food came first. The venue’s in-house culinary team had been part of its appeal from the beginning, and dinner, along with the estate’s cookies, ended up becoming one of the things guests continued talking about afterward.

Music came next. Rather than treating the band as background entertainment, they saw it as the piece that would determine how the reception moved. The dance floor stayed full, with friends and family singing and dancing together well into the night.

Photography was another priority, particularly because Jackie and Trent had chosen not to do a first look. Their photographer helped them find a compromise that became one of their favorite parts of the day. Before the ceremony, they stood back to back and held hands without turning around to see each other. From there, they read their private vows to one another.

“It gave us a quiet moment to slow down, connect, and share our hearts before the excitement of the day began, while still preserving the emotion of seeing each other at the ceremony,” Jackie says. Careful scheduling also meant that skipping a first look didn’t cost them the entire cocktail hour. After portraits, the newlyweds were able to join their guests, eat the appetizers, and spend time with people before everyone moved into the reception.

Why a Less-Is-More Approach Worked at Willowdale Estate

Jackie describes herself as a Type A bride, so handling most of the planning herself, with considerable help from her mom, suited her. Their guiding idea was equally straightforward: “less is more.” They kept things simple with white flowers, soft greenery, candles, and natural wood accents. A custom dance floor featuring their wedding logo added a personal touch to the reception space.

The smaller details had more personality. Jackie’s stepdad built the seating chart by hand and added the phrase “Please Be Seeded,” connecting it to the wildflower seed packets waiting for guests. Friends and relatives have since sent the couple updates after planting them.

Each place setting also had a ribbon printed with the guest’s name, while custom coasters could be used during the reception. Rather than asking everyone to sign a book, Jackie and Trent set out personalized playing cards for guests to leave notes on, giving them something they would actually want to revisit after the wedding.

Letting the Reception Get a Little Less Formal

Once the reception started, much of the carefully restrained New England styling gave way to the party Jackie and Trent had prioritized from the beginning. The band kept people on the dance floor, and the couple eventually started throwing custom “The Jenkins” hats into the crowd. Soon, friends and relatives were dancing in them. Even dessert had a small departure from tradition. Rather than a standard wedding cake, Jackie and Trent chose a heart-shaped raspberry tiramisu cake.

Those choices worked because they weren’t trying to make every part of the wedding conform to the same aesthetic. The ceremony could have private vows and a song written by Trent’s father. Dinner could focus on genuinely good food. The reception could involve hats flying across the dance floor.

Their Advice: Don’t Let the Small Decisions Take Over

After planning much of the wedding herself, Jackie’s advice is to be selective about what gets your energy. “It’s so easy to get caught up in the little details and everyone else’s opinions, but don’t let them take away from the joy of the process,” she says. “The things you spend months worrying about usually aren’t what anyone remembers.”

For Jackie and Trent, that meant putting their money into food, music, and photography, keeping the decor relatively simple, and trusting a vendor team that already understood how to work together. The rest came down to the things no other couple could duplicate: messages hidden inside a tuxedo and wedding bands, flowers grown from seed packets months later, notes written on playing cards, and a song Trent’s dad wrote just for them.