A Summer Wedding Inspired by the Bride's Grandmother's Garden at a Family Property on Cape Cod, MA
Not much sticks around after freshman year of college, whether it’s friends, fashion choices or (what you thought would be) your major. But for Sydney Ellis and Jake Weil, something special happened then that stood the test of time: They made a pact—half in jest—to someday marry. The two met in 2011 while attending Dartmouth and kept things platonic during their college years. Although there was a moment during Jake’s Senior Day lacrosse game that hinted to their playful freshman promise and to their bright future.
“I stood in the stands with a handmade sign that read, ‘Weil You Marry Me?’,” says Sydney. “Little did we know it foreshadowed what was to come.” The pair remained just friends for nearly a decade, until they reunited in NYC in summer 2021. By winter, the duo was dating and “in it for the long haul,” she says.
The couple got engaged in August 2024 at Anchor to Windward, a summer property in Osterville, Massachusetts that’s been in Sydney’s family for three generations. They were attending a family friend’s barbecue, and Jake had planned to leave early with his then-girlfriend to propose back at the house. But there was one hurdle to overcome: Sydney’s social butterfly energy. “What I didn’t anticipate was that it would be a 10/10 day,” Jake recalls, “and Sydney, being the life of the party, refused to leave.” (Eventually, he persuaded her to go by faking an illness.)
Back at Anchor to Windward, he asked Sydney to walk him through her dream wedding, knowing the tour would end at her favorite spot: her grandmother’s garden overlooking Cape Cod’s West Bay. Jake got down on one knee and asked for Sydney’s hand before the blooms. Post-“yes!,” they shared Aperol spritzes and an impromptu dip in the bay, before joining the Ellises for a boat ride and dinner under the stars. It was their engagement locale, the place their families had met, where they spent summers and the setting of three other family weddings, so Anchor to Windward was the natural choice for the festivities. The pair took care to curate a slate of celebrations that captured the vibrancy of a summer weekend spent there, ensuring guests always had access to great food, vibes and company. “We both felt very strongly that, if we were going to ask people to travel for our wedding, we should make sure they had meals and activities available,” says Sydney. “After attending 17 weddings the previous year, we knew that small gestures make a big difference.”
The mid-September wedding weekend kicked off with an intimate clambake rehearsal dinner on the property’s beach—though with the pair’s 29(!) bridesmaids and groomsmen, it was still a full house. As a nod to the Ellis family’s annual Fourth of July party, guests wore red, white and blue to match “Americana-themed” picnic tablescapes. The meal finished with cookies made by Jake’s cousin’s bakery, then the party opened to all guests, who partook in fireside s’mores and many rounds of “Dartmouth pong” (beer pong played with Ping-Pong paddles). “Starting the weekend off with our toes in the sand, surrounded by our closest friends and family, was very special,” says the bride. A wink to her sustainable-fashion career, Sydney incorporated secondhand pieces into every outfit in her wedding wardrobe. One of her most noteworthy ensembles was a strapless skirt-and-top set, crafted from her mother’s 1981 wedding dress for the Friday-evening welcome party, complete with a scarf fashioned from its lace sleeves. The perfect finishing touch: her grandmother’s Nantucket basket bag, adorned with an etching of Anchor to Windward. The welcome party took place at the Osterville Historical Museum, where guests enjoyed lawn games, live music and food trucks serving lobster rolls and wood-fired pizza. The couple chose the rural-ish setting as an homage to their New Hampshire college town, but that wasn’t the only aspect of the evening that recalled fun times: Nine loved ones gave toasts, each funnier than the last, according to the couple.
“The night ended up feeling more like stand-up comedy than a wedding event,” says Sydney. In keeping with the Ellises’ long-held tradition of wedding musical tributes, her cousins sang “Texas Hold ’Em” by Beyoncé (the bride’s favorite artist), with a few lyrics tweaked to be about the couple, to cap off the night.
The next day—September 13, 2025—150 guests gathered at Anchor to Windward to watch the lovebirds wed. On the property’s beach, a boardwalk aisle was flanked with woven baskets of natural eelgrass, ending at a chuppah perched at the edge of West Bay that was wound with delicate vines and white flowers. The groom arrived by boat to the ceremony, and the bride—looking radiant in a custom gown and a borrowed veil from her cousin—descended to the shore on the arm of her father to Ben Howard’s “Old Pine,” a nod to Dartmouth’s Lone Pine emblem. Officiated by Sydney’s brother-in-law, Nick, the ceremony was a highlight. “It was surprisingly fun, with Nick taking us through a detailed investigation into who caught feelings first over the decade we had been ‘just friends,’” says Sydney. “It was so clever and personal—we laughed throughout the whole thing.” Nick also emphasized the couple’s strong relationship, built on trust, adventure and the ability to light up every room.
A college pal read Robert Frost’s “The Road Not Taken,” then the couple recited their personal vows—both mentioned committing to a foundation of friendship. “It’s a funny thing, falling in love with your best friend,” says Sydney. “It’s scary, and exciting, and risky and incredibly rewarding.” After “I do,” the newlyweds departed aboard a Hinckley Picnic Boat captained by Sydney’s dad’s childhood best friend, as guests tossed flower petals from the dock. The pair was excited to catch up on their respective wedding mornings while sipping some just-married champagne. Back ashore, guests also celebrated with bubbly: A toast on the beach flowed into cocktail hour on the lawn. Attendees mingled over two signature cocktails—a tequila cosmo built from the father of the bride’s recipe, and the Dartmouth-influenced Big Green with notes of cucumber and lime—as well as tuna tartare, spring rolls and a raw-bar.
A floral fete inspired by the couple’s engagement spot followed: “My grandmother’s garden served as our main inspiration, as it’s the first thing you see when you drive up to the house,” says Sydney. A sailcloth tent spanned over the spot where Jake had popped the question, positioned so the garden’s lush flowers bloomed along one side. Along with beachy rattan details, petals popped up all over the reception space, from the centerpieces bursting with coral roses to the pressed flowers adorning the cake and escort cards.
The revelry began with the couple’s first dance, to “Real Love Baby” by Father John Misty. “ We can’t really remember when it became our song, but we always knew we’d choose it,” says the bride. “We choreographed the dance ourselves—a little last minute, which is typically how we do things—so we also used our solo boat ride after the ceremony as a last chance to rehearse.”
Dances for the bride and her father and the groom and his mother followed, plus one more special number: The newlyweds surprised Sydney’s sister (the maid of honor) and brother-in-law (the officiant) with the “first dance they never had.” (Their own wedding was canceled during the pandemic.) “They did so much for us throughout the process,” says Sydney. “It made us so happy to give them something as a thank-you.”
As the sun set, attendees dined on miso-glazed salmon, chimichurri skirt steak and sides served family style, and wedding cake (with one lemon-raspberry layer and one red-velvet-espresso layer). The bash continued with beach bonfires and a silent-disco after-party in the boathouse that rivaled the couple’s college nights spent dancing in the Theta Delta Chi fraternity basement. And when the bride’s dad turned on the disco ball, the merrymakers were all for it. “The entire crowd went nuts,” says Sydney. “We didn’t stop dancing until the early morning.”
The couple’s wedding festivities concluded the same way as their proposal, with a joyful jump into the waters of West Bay. (The maid of honor played lifeguard.) It was a worthy send-off to a summer of celebration at Anchor to Windward, sure to be reminisced over for seasons to come.