2nd Annual Greenport Holiday Stroll

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 (October, 2025) — 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. 

Guests can check in at the Harbor Front Inn lobby to pick up their event booklet — complete with a map, list of participating businesses, 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 of 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. “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 

• Local Business Holiday specials & offerings list featuring everything that’s happening during 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, & more!

• Live music and caroling throughout the village
• Live Dance groups with dedicated timed performances including Inspire Dance Center  

• 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 trucks & tractors for pictures.
• Meet Santa at the Old School house for photos!
• Check out the Village Blacksmith open with demos 
• Fire pits along the Front St. closure to stay warm throughout the stroll
• Cops & Cocoa outside of Aldo’s Coffee Compnay & a decorated holiday cop car 
• Stirling HIstorical Society & the Ireland House will be open 

Holiday Booklet provided at check-in at Harbor Front Inn with event map, Bingo card, and special offers