The Oyster Bay Holiday Market and Winter Stroll will return on Dec. 14, marking its fourth year as a centerpiece of the community’s holiday season. Organized by Oakcliff Sailing, the Oyster Bay Main Street Association and the Oyster Bay-East Norwich Chamber of Commerce, this event promises a day filled with shopping, entertainment, and holiday cheer.
The expanded holiday festivities, which began during the pandemic in 2020, have quickly become a cherished tradition. Executive Director Meredith Maus of the Main Street Association described the event as “a great way to show off how special this community is,” combining holiday spirit with support for local businesses.
The market will feature dozens of local vendors, fire pits, and live entertainment throughout the downtown area. Holiday shopping will be central to the event, with local stores and market stalls offering unique gifts. Tree sales and gift-wrapping services will be available at the Oyster Bay Community Rowing’s warming tent, ensuring that attendees can check items off their holiday to-do lists with ease.
The family-friendly festivities will include:
Ice Skating from 1 to 5 p.m. near Stellina Bakery, sponsored by the OBMSA.
Holiday Hayrides provided by Wonderland Tree.
Raynham Hall Museum’s virtual reality tours, showcasing an immersive historical experience.
Performances at the bandstand by local groups such as the Oyster Bay-East Norwich High School Choir and dancers from Gone Dancing.
Santa Claus is scheduled to arrive with his firefighter escorts at 4 p.m. to light the community tree, a highlight of the evening that will coincide with menorah lighting.
The Holiday Market is a collaborative effort involving several local organizations, including Oakcliff Sailing, which provides ‘elves’ to assist shoppers with tree transport and helps distribute toys with Santa. Other community partners, such as Friends of the Bay and the Oyster Bay Civic Association, will host booths and activities.
“This event is really a reflection of how our community comes together,” Maus said. “It’s not just about the holidays, but about showcasing everything that makes Oyster Bay a great place to live and visit.”
In addition, the Long Island Herald’s Window Decorating Contest will feature storefront displays competing for public votes. Winners, determined by a combination of public and expert voting, will be announced at the tree lighting and awarded a feature in the Oyster Bay Herald.
Maus emphasized the dual goals of fostering holiday spirit and supporting the local economy.
“Anytime you bring the community together, it makes the community stronger,” she said. “This is about more than just the holidays—it’s about highlighting what we have here in Oyster Bay.”
From live music and hayrides to one-of-a-kind gifts, the event aims to create lasting memories while celebrating the season and the town’s unique character.
The Holiday Market runs from 1 to 5 p.m., with the tree lighting ceremony beginning at 4 p.m. Parking will be available at Fireman’s Field, with ‘elf’ transport courtesy of Oakcliff Sailing. Attendees are encouraged to dress warmly and bring reusable shopping bags, which will be provided by Renaissance Properties.
For updates and more information, visit the holiday markets website OysterBayHolidayMarket.com or contact event organizer Dawn Riley at (415) 760-7642.
