2nd Annual Greenport Holiday Stroll & Harbor Front Night Market Returns
to Light Up the Village This Season
Friday, December 19, 2025 | 5:00–8:00 PM | Downtown Greenport Village
Greenport, NY — The Harbor Front Inn and the North Fork Art Collective are proud to present the 2nd Annual Greenport Holiday Stroll & Harbor Front Night Market, a festive evening celebrating community, creativity, and local culture in the heart of the village.
Taking place on Friday, December 19th, 2025, from 5:00–8:00 PM, this beloved event invites residents and visitors alike to explore the Downtown Greenport Business District, featuring local artisans, seasonal treats, live music, and holiday cheer throughout Front and Main Streets (including a few stops on Carpenter St. & First St.)
Guests can check in at the Harbor Front Inn lobby to pick up their event booklet — complete with a map, list of participating businesses (over 45 businesses are participating), and a Holiday Bingo Card featuring 24 stops across the village. As guests stroll, they can visit shops, galleries, and restaurants offering festive cocktails, pop-up vendors, interactive photo ops, and sparkling window displays. All guests who complete their bingo card are entered in a raffle to win a goodie bag from local businesses & a one-night stay at Harbor Front Inn.
Meanwhile, the Harbor Front Inn, The Menhaden, & Little Creek’s Hold Fast Studio, will host a curated Night Market, spotlighting local makers, artists, and small businesses offering handcrafted gifts and holiday treasures.
“The Holiday Stroll is about coming together as a community and supporting the small businesses and artists that make Greenport so special,” said Kara Hoblin, Director of Guest Culture & Experiences at the Harbor Front Inn, Owner of The North Fork Art Collective & creator of the Greenport Holiday Stroll. “It’s an evening filled with warmth, light, and connection, the perfect way to close out the season. We are grateful to partner with the Village of Greenport & the Greenport BID this year to continue to build the stroll into a tradition for years to come."
Event Highlights
Over 45 Local Business Holiday specials & offerings list featuring all participants partaking in the Stroll
24-stop Holiday Bingo Challenge encourages guests to explore shops, restaurants, and galleries (no purchase necessary for a stamp on the bingo card!)
The Greenport Antique Carousel will be open with free rides for children under 12 sponsored by The Friends of Mitchell Park
Local Artisan Night Market at Harbor Front Inn & The Menhaden lobbies featuring handmade gifts and holidaywares, as well as in Little Creek’s Hold Fast Studio on Main St. Featured Artisans: Sasha Samuel Jewelry, Nofo Style, Disset Chocolate, Red Earth Herbals, NFAC artists; Jackie Dandelion, Paul Brooke, Katie Kooks, & Allison Co. Designs, Wild Muse, Bridge & Sound, & more!
Live music and caroling throughout the village with performances by the First Baptist Church of Greenport Carolers & Dave Berson. The GHS Acapella will begin at Harbor Front at 6pm and visit multiple businesses down Front & Main until 7pm. Catch them if you can!
Live Holiday Dance show at our roped off “Street Stage” by Inspire Dance Center at 5:30pm & 6:30pm.
Festive décor and photo moments along Front and Main Streets. The road will be closed from 3rd st. (Menhaden) to 1st st. (Aldo’s) featuring decorated fire trucks, a tractor thanks to Sepnoski Farms, a boat from The East End Seaport Museum & others for pictures.
Meet Santa & Mrs. Clause at the Old School house for photos with Madison Fender Photography!
Village Schoolhouse will be open with crafts from C.A.S.T. and a food drive as well as storytime with Nina Keller Children's Librarian from Floyd Memorial Library
Check out the Village Blacksmith open with demos with Tom the Village Blacksmith
Fire pits along the Front St. closure to stay warm throughout the stroll sponsored by American Beech in partnership with The Greenport Fire Department.
Cops & Cocoa outside of Aldo’s Coffee Compnay & a decorated holiday cop car by Southold Town PD
Stirling HIstorical Society & the Ireland House will be open from 5-8pm
Holiday Booklet provided at check-in at Harbor Front Inn with event map, Bingo card, and special offers!