On Thursday, June 19, the charming hamlet of Oyster Bay will once again open its gates and garden paths to the public for one of its most beloved community events: the Oyster Bay Garden Tour. Now in its renewed third year after a decade-long hiatus, the tour showcases the beauty of private gardens across the North Shore while supporting the ongoing beautification efforts of the Oyster Bay Main Street Association (OBMSA).
The Garden Tour is more than just a feast for the eyes; it’s a grassroots effort with deep community roots and a clear mission.
“We started this back in 2011 as a way to put Oyster Bay on the map,” said Danielle Olesen, co-chair of the OBMSA’s Beautification Committee. “It’s a destination town—you don’t just drive through Oyster Bay. You have to want to come here. And we wanted to give people a reason to do that.”
Founded by Olesen and co-chair Colleen McKean, the original garden tour ran from 2011 to 2014 before taking a long break.
“We can’t even remember why we skipped 2013,” Olesen joked. But in 2023, they brought the tour back—this time with a broader purpose. “We created the Beautification Committee to address real issues in our downtown—like trash buildup and lack of maintenance. And we revived the garden tour to help fund those solutions.”
The Beautification Committee’s impact is already visible. Thanks to proceeds from past tours, they’ve hired a street-sweeping company to regularly clean the downtown area, installed seasonal plantings and hung flower baskets throughout the business district.
“It makes a difference,” Olesen said. “When you drive into Oyster Bay now, from any direction, you can see that it’s loved and cared for.”
This year’s tour features three unique private gardens—all previously unseen on past tours—in Glen Cove, Oyster Bay Cove and an estate near Planting Fields Arboretum. The locations remain a secret until the day of the event, adding an air of anticipation.
“One of the gardens is significantly larger than anything we’ve had before,” said Olesen. “So we reduced the number of stops this year to make sure people have time to explore and enjoy it.”
The event begins with registration at the Oyster Bay bandstand near town hall, after which participants drive to each garden in their own cars. Groups are staggered to ensure a comfortable experience, with no more than 25 to 30 guests at a garden at any given time. Docents—all local volunteers—are stationed at each location to guide guests and provide insights.
“It’s a friend-powered event,” Olesen said. “Our committee is just a group of friends—one takes photos for the tour program, others run the raffles and even our college-age kids pitch in directing parking.”
Adding to the experience are tastings provided by Oyster Bay restaurants at each garden stop, offering visitors a literal taste of the local flavor. The day concludes with an optional cocktail party at Cooper Bluff, a waterfront venue near Sagamore Yacht Club. While it’s a cash bar, food is provided and the party features raffle prizes donated by local businesses.
“Everything is hyper-local,” said Olesen. “From the food to the raffle items to the gardens themselves—this event is all about celebrating our town and bringing the community together.”
One of the guiding principles of the tour is accessibility and inspiration. While the grandeur of estate gardens is certainly on display, the organizers also make sure to include more relatable properties.
“We want people to walk away with ideas they can use in their own backyards,” Olesen explained. “You don’t need an enormous property to have a beautiful garden.”
This year, one of the featured gardens even includes a private landscape artist, who will be available during the tour to answer questions and discuss design choices.
“It’s a great opportunity for people who are serious about gardening or just looking for inspiration,” Olesen added.
The OBMSA is hoping to increase attendance this year, especially since the tour falls on Juneteenth—a public holiday, giving more people the chance to attend. They are even exploring a partnership with the Boys & Girls Club of Oyster Bay-East Norwich to offer childcare for parents who want to enjoy the tour worry-free.
Proceeds from ticket sales continue to fund the committee’s downtown improvement projects. “It’s all about reinvesting in Oyster Bay,” said Olesen. “Every dollar goes back into making this place more beautiful and welcoming.”
Tickets for the 2025 Oyster Bay Garden Tour are now available through the OBMSA website at oysterbaymainstreet.org or at obmsa.givecloud.co. Options include tickets for the tour, cocktail party or both.
“It’s just a lovely day,” Olesen said. “We work hard, but we have a great time doing it. And it’s for a great cause.”
Whether you’re a seasoned gardener, a history buff or simply looking for a relaxing day in one of Long Island’s most picturesque towns, the Oyster Bay Garden Tour offers a rare glimpse into private landscapes, a sense of local pride and the warmth of a community blooming with purpose.
Read also: 8 Beautiful Botanical Gardens Right in New York City and on Long Island
