Real Weddings

A Stockbridge Farm Wedding with Horses, a Plane, and Late-Night McDonald’s

Massachusetts residents Katherine and Harley Waller also celebrated with a "Pink Pony Club" after-party.

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Bride and groom walking down a white aisle outdoors, surrounded by guests seated on wooden chairs. The bride wears a white gown with lace sleeves and holds a bouquet of white flowers, while the groom wears a black tuxedo with a bow tie and glasses. The aisle is decorated with white floral arrangements, and the sky is clear with visible contrails.

Photo by Hassan Hadad

For Katherine and Harley Waller, love seemed meant to be since they had been in each other’s orbit for years. The pair first met at boarding school in the Berkshires, where Harley was friends with Katherine’s older brother. Years later, when she moved to Boston for college, her brother encouraged her to reach out to a familiar face also living in the city. “We started dating pretty much immediately,” Katherine says. Nine years later, Harley proposed on Nahant Beach at sunset, with their beloved dog, Braxton, by their side, just days after Katherine’s father suffered a heart attack. “It’s kind of crazy how it all happened,” Harley recalls. While jokes were made about the timing, the family felt nothing but joy after her father recovered and wedding planning began.

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Although the bride grew up spending summers in Hyannis Port, originally imagining the big day there, the couple soon realized Harley’s family farm in Stockbridge was actually the ideal destination. “We spent a lot of time there, and it became a really special place for us,” Katherine reveals. A sprawling property dating to 1902, the farm has been home to generations of horses, history, and heartfelt celebrations. “There’s a level of formality to the property, but there’s also a level of comfort,” Harley adds. The weekend’s standout moments included the couple’s horse-drawn arrivals—Harley in a vintage Bugatti carriage and Katherine in a smaller one alongside her father in a top hat—their ceremony beneath the family’s heirloom arbor, and a champagne-sabering reception that gave way to a glowing “Pink Pony Club” after-party, complete with a brass-band parade and late-night McDonald’s delivery. “It was perfect,” Katherine says. “We really had the best time ever.”

A long dining table set with white plates featuring a beaded edge, crystal glassware, and black cloth napkins. Tall white taper candles in black candle holders and white floral arrangements with greenery run down the center of the table. Wooden chairs with woven backs surround the table. The setting is bright and elegant.

Photo by Hassan Hadad

A brown and white dog with a collar sits on an ornate red and gold patterned couch with green pillows. In the background, a man wearing black pants, suspenders, and a white shirt is adjusting his bow tie in front of a mirror. The setting appears to be a warmly lit room with wooden accents and window blinds.

Photo by Hassan Hadad

The Details

THE THEME

“Our big theme was we wanted to make sure we had a good environment for both our younger crowd to have fun and dance, and our older crowd to have areas where they could sit, chat, socialize, and have a good night without worrying about everything being so loud, hectic, and hard to get to,” Katherine reveals. “I think we really pulled that vision off. Mandy [the wedding planner] did such a great job making sure that everyone was really comfortable .”

A circular outdoor wedding ceremony setup on a grassy field with wooden chairs arranged in a wide ring around a white aisle. At the center of the aisle is a floral arch decorated with white flowers. The background features distant trees and rolling hills under a clear blue sky.

Photo by Hassan Hadad

THE FAMILY TRADITION

A tradition that’s literally rooted in the family’s farmland is to marry under a specific arbor located on the property. “Everyone in the house who got married under there has had very long and happy marriages,” Katherine reveals. “It was built for my parents,” Harley adds. “They got married there in the 1980s, and there hasn’t been a bad marriage underneath it.”

THE BAND

“Our wedding planner sent us a bunch of bands, and we listened to all of their different samples. We found this one band [Ripcord]. The two singers were just incredible, and they have this award-winning brass section that is internationally known,” Harley says. “We just couldn’t live without them. It was definitely really high on the budget, but it was so essential. They really made the whole evening.”

Six women wearing matching black ruffled dresses are walking on a grassy field, each holding a small bouquet of white flowers. The background features tall green trees and a clear blue sky.

Photo by Hassan Hadad

THE FIRST DANCE

After some photos, the couple was announced into the reception tent, where they had their first dance to “You Make Me Feel Like Dancing” by Leo Sayer. “We had a little mix-up with that, where we weren’t used to it. We were only used to the recording—not someone performing it,” Katherine shares with a laugh. “So we missed our first mark and just improvised it,” Harley adds. “No one knew. It was great. We just did our moves.” It was very “them,” the bride continues, “because we were giggling the whole time.”

THE CAKE

While at some weddings the cutting of the cake is an event in and of itself, Katherine and Harley wanted everyone to just keep enjoying cutting a rug on the dance floor. “We didn’t do it traditionally and have everyone go around us,” the bride explains. “We had the cake off to the side, and we did it privately, which was great. We got great pictures. We had a lot of passed desserts because we just wanted to dance.”

A vintage-style biplane model decorated with clusters of white and light pink hydrangea flowers, positioned on a grassy area with trees and hills in the background. The plane has a wooden propeller and the text "Vigo Motor Oil" on its side.

Photo by Hassan Hadad

THE AIRPLANE

In addition to the vintage carriage that was stationed inside the big tent for the reception, another showstopping decorative piece was a small World War I–era airplane. “After I drove the coach to the ceremony, we put it on one side and then this airplane on the other,” the groom explains. “It was a really cool feature because it’s fully functioning, and people could actually climb into it.”

A horse-drawn carriage with red wheels and black body carries a bride in a white dress and veil, accompanied by a man in a black suit and top hat. Two men in black suits and top hats are seated at the front, driving two brown horses. The scene is set on a gravel path with green grass and trees in the background.

Photo by Hassan Hadad

A man wearing a black riding helmet, glasses, white shirt, beige pants, and brown riding boots is sitting on a brown horse with white markings on its legs and face. Next to them, a woman with blonde hair, dressed in a brown jacket, white pants, and black and brown riding boots, is standing and holding the reins of another brown horse with a white blaze on its face and white markings on its legs. The background shows a white fence, green trees, and hills under a cloudy sky.

Photo by Hassan Hadad

THE HORSES

While the horses played an important part leading the couple to the ceremony in their respective carriages, that wasn’t the only role they took on. “Some of the amazing staff who work at the farm brought up two of the horses so everyone in the tent could pet them,” the bride reveals.

Eight men dressed in black tuxedos with bow ties are walking on a grassy field under a clear blue sky. Four of them in the front are holding glasses with drinks, and they appear to be smiling and engaged in conversation. Trees and a fence are visible in the background.

Photo by Hassan Hadad

THE AFTER-PARTY

The after-party theme was the “Pink Pony Club,” and its big reveal didn’t disappoint. “The lighting team was able to make it look almost like a landing strip all the way from our big tent down into what we call the ‘Party Barn,’” Katherine reveals. “The band turned into this Louisiana-style marching band,” Harley adds, “we all marched down there together.” The band played a few songs with the DJ, and later, multiple McDonald’s Happy Meals were brought in for late-night snacking.

Four rings, including a diamond engagement ring and three gold bands, are displayed on a white card with the initials "K / H" printed on it, placed on a green surface. Nearby is a decorative brush with a carved handle and light brown bristles, along with a white card featuring elegant script text.

Photo by Hassan Hadad

The File

Band Ripcord
Bride’s Dress (Ceremony) Amsale with custom Vera Wang sleeves and veil
Bride’s Dress (Reception) Anne Barge
Cake and Caterer Mezze Catering
Flowers Fleur Events
Groom’s Attire Hive & Colony
Hair & Makeup Jeannie Reilly-Ortega
Lighting & Draping SociaLight Boston
Photographer Hassan Hadad
Planner & Designer Hummingbird Events & Design
Shuttles AA Transportation

White pointed-toe high heels with large bows on the front, hanging from an ornate gold wall sconce with two white taper candles. The shoes have pink insoles with floral designs and the Valentino logo.

Photo by Hassan Hadad

A bride in a white wedding dress and a groom in a black tuxedo are seated in a dark green vintage convertible car with tan interior, parked on grass with a large leafy bush and clear blue sky in the background.

Photo by Hassan Haddad

Dark green vintage Triumph convertible with tan interior, wire-spoke wheels, and chrome front bumper, parked on grass with trees and a clear sky in the background.

Photo by Hassan Hadad

First published in the print issue of Boston Weddings 2026 with the headline, “Landmark Occasion.”

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