The bride wore white. The groom wore a tuxedo. The golden summer sun was going down over the beach in Baiting Hollow. Flowers lined the aisle, photographers jockeyed for the best angle. The Long Island Sound offered up a picture-perfect backdrop from the crest of a waterfront bluff.
But Olivia Delay and Jack Drillock, while newly betrothed, weren’t getting married. They were helping launch a new East End business built around bringing local wedding vendors together. It was a carefully engineered bridal shoot event designed to showcase hamptonBRIDE.com, a new East End wedding platform founded by Hampton Bays entrepreneur Kerry Wilkie.
Delay and Drillock are a newly engaged couple whose story seemed almost perfectly suited to the setting. They had become engaged only weeks earlier on a cliff in Sorrento, Italy. Now they were standing on another bluff, this time in Baiting Hollow, surrounded by photographers, florists, stylists, bakers and bridal professionals who had donated their time, goods and services to promote not just one business, but an entire East End wedding network.
Building a one-stop wedding platform
The new venture, hamptonBRIDE.com, is Wilkie’s attempt to create the kind of centralized, locally-rooted resource she wished had existed when she planned her own wedding. The site pulls together venues, florists, photographers, makeup artists, bakers, bridal boutiques, accommodations, as well as specialty vendors serving the East End. Couples can begin with a venue, then move through the rest of the planning process without searching dozens of disconnected websites.
“They begin their wedding journey,” Wilkie said. “They can choose venues or different specialty vendors. There’s something for everyone.”
Wilkie also owns the digital marketing agency Marketing by Click. She uses that experience to position hamptonBRIDE.com in search results and drive prospective couples to the site, giving small local businesses online exposure they may struggle to afford on their own.
“We spend the money on the marketing, where our vendors don’t have to,” she said. “It’s a nice collaboration.”
The site is intended as a hyperlocal alternative to national wedding directories, which can return results far outside the East End, even when couples search specifically for a North Fork or a Hamptons venue, Wilkie said.
She wants the platform to reflect not only the region’s major venues, but also the small businesses and lesser-known locations that give East End weddings their character. That can include welcome-bag vendors, specialty cocktail trucks, gelato carts, live engravers and unusual entertainment.
“A wedding isn’t just a wedding anymore,” Wilkie said. “It’s an experience that unfolds over an entire weekend.”
Couples want guests to remember not only the ceremony and the bride’s dress, she said, but also the signature drinks, floral installations, desserts and small details that make an event distinctive — and highly shareable on social media. The Baiting Hollow shoot — arranged by Wilkie’s friend Teri Whitcraft, who owns the home with her partner — was designed to demonstrate that 360-degree approach in real time. The waterfront property is known as ‘Wabi Sabi,’ a traditional Japanese term for ‘beauty in imperfection.’
A ‘difficult journey’
The idea for hamptonBRIDE.com began long before its October launch. Wilkie and her husband, Paul, had discussed creating the platform for years, but planning their own wedding gave the project urgency. Wilkie assumed her digital marketing background would make the process straightforward. Instead, she encountered outdated websites, incomplete information and no single resource devoted specifically to East End weddings.
“I’m the Google lady,” she said. “So I’m looking things up, and a lot of the places out here, they’re a little bit behind digitally.”
Eventually, she told Paul they had to stop searching online and get in the car. The couple toured venues and considered vineyards before arriving for lunch at their favorite restaurant, Oakland’s Restaurant & Marina in Hampton Bays. Paul asked an obvious question: Why weren’t they getting married there?
“We’re so happy we ended up there,” Wilkie said. “But the journey for people searching is difficult.”
Their celebration was East End all the way. Guests stayed at the Hampton Maid, where the couple also held brunch. Wilkie arranged to take wedding photographs behind a local seafood business after noticing its view over the bay.
That experience became part of the hamptonBRIDE.com philosophy, she said. Local professionals know the hidden corners, scenic overlooks and unexpected locations that couples arriving from elsewhere may never discover.
Wilkie and her husband began building the site in March and launched it in October. She now visits venues personally, meets vendors and observes them in action whenever possible. Styled shoots serve both as marketing opportunities and a form of quality control. She does not want merely to list a business. She wants to understand what it does and how it works with clients.
Finding Olivia and Jack
For hamptonBRIDE.com’s first large-scale bridal giveaway, Wilkie wanted more than professional models. She wanted a real couple carrying the unmistakable energy of a new engagement. Delay and Drillock were engaged only weeks earlier, when Delay spotted the contest on Instagram.
After returning from Italy, the couple had already begun exploring hamptonBRIDE.com. Both knew they wanted to marry on the East End, where their families had spent summers since they were children. Drillock’s cousin, who was also planning an East End wedding, had recommended the site. As part of the contest, Delay followed the photographer involved in the giveaway, tagged several people and completed a short form explaining the couple’s connection to the Hamptons.
The prize included the fully styled shoot and access to the complete gallery of professional photographs. “I can’t even believe we won something like this,” Delay said. “This house is gorgeous. We’re just very excited to be here.”
Jeremy Garretson photos
The love story came with an unexpected twist. After the couple arrived, Wilkie discovered she knew members of Drillock’s extended family from college and had already helped several relatives with weddings or proposals. Drillock’s aunt had been in her sorority. His uncle had been one of her close friends at Iona University. The HamptonBride.com co-founder had helped other family members find photographers, planners and wedding services.
Drillock had not mentioned those connections when the couple entered because he did not want preferential treatment, he said in an interview. Wilkie said the discovery made the day more personal, and underscored how interconnected the East End wedding community can be.
‘Invisible strings’
Delay, 27, a nurse at NYU Langone Hospital in Mineola, and Drillock, 28, who works in real estate acquisitions, met on Hinge about three years ago. It took awhile, but they began discovering how many connections already existed between their families. One Christmas morning, Delay’s name appeared on Drillock’s car display while he was driving with relatives. His mother recognized the surname and asked whether Delay’s mother was a hairdresser. She was.
Delay’s mother had done Drillock’s mother’s hair for her wedding. The families had also moved through overlapping social circles, spent summers in the Hamptons and frequented many of the same beaches and places without Olivia and Jack ever knowingly meeting.
Delay describes it as the “invisible string theory” — the belief that two people can be connected long before they understand how.
“We could have been on both sides of Ponquogue Beach, each on the other end of the lifeguard, just not even knowing we were there,” Delay told the Sun.
Drillock proposed during a family trip to Italy. At sunset in Sorrento, overlooking the Mediterranean, he surprised Delay with flowers, champagne and a photographer. “It was picture perfect,” she said. “I told him my dream proposal would be just the two of us, and then to meet our family after, and that’s exactly what we did.”
The cliffside setting in Italy made the Baiting Hollow shoot feel almost like a continuation of their engagement story. Weeks after Drillock proposed above the Mediterranean, the couple found themselves dressed as bride and groom on a second windswept cliff overlooking the water. They plan to marry at Oceanbleu on Dune Road in Westhampton Beach.
A showcase for local talent
The shoot also highlighted several independent businesses hamptonBRIDE.com was created to promote, including wedding photographer Michael Cassara, Jenny Smith Gugliada and Mike Gugliada of the Cutchogue flower farm Lily Pad Acres, Nikki Lee Favata of Ink & Ivy Hair, Lauren Lombardi of the Lauren Lombardi Events, Dan Castrogivanni and Steph Servedio of Waterfront Aisles — which designs luxury aisles for outdoor weddings — and Irene Rodriguez Manieri, owner of Veg on Board, who designed and created the couple’s wedding cake. Alexis Verdi and Sam Hubbard from AV Content Ltd. were the content creators.
Manieri specializes in vegan and allergy-friendly custom cakes for weddings and other events. While Delay and Drillock are not vegan, but Manieri said modern couples increasingly seek desserts that accommodate a range of dietary needs without sacrificing presentation.
She has operated Veg on Board for six years from the Stony Brook Food Business Incubator’s commercial kitchen in Calverton. When an oven explosion temporarily closed the kitchen, she relocated production to Southampton College to keep the business running.
Lauren D’Abramo, owner of Beauty by Lauren, handled Delay’s makeup. D’Abramo has worked professionally in makeup since about 2009 or 2010, building on a background in fine art. She had only recently joined hamptonBRIDE.com after learning about the platform through a photographer.
The Baiting Hollow event was her first shoot with the company and one of the largest on-location productions she had joined. Her company provides makeup, hair and spray-tanning services. D’Abramo added spray tanning after brides repeatedly asked where they could find a reliable local provider. Her favorite moment, she said, comes when the finished look is revealed.
“When a bride looks at themselves after they’re all put together and glammed up, they just have this glow in their face,” she said. “It makes people feel feminine and empowered.”
Ali Regan and Megan Rigby, co-owners of Hamptons Bridal boutique in Southampton, supplied the gowns. The two opened the boutique after recognizing a gap in the regional market: There was no dedicated wedding-dress shop in the Hamptons. They developed the idea in 2024 and opened their doors in 2025, curating a collection featuring designers unavailable elsewhere on Long Island.
For the Baiting Hollow shoot, they brought several options, including gowns and a party dress, allowing Delay to choose among different looks in real time. Both women came from luxury retail backgrounds, but quickly discovered that bridal fashion is different from ordinary shopping.
“It’s not like you’re just going and buying a pair of jeans and leaving,” Regan said. “It’s a very memorable part of the wedding journey.”
Each appointment at their boutique is private. The doors are locked, the bride has the showroom to herself, guests are invited and champagne is served.
“We make it feel like you’re coming into our home,” Regan said.
