The Harbor Front Inn and the North Fork Art Collective present the second 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 19, from 5 to 8 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 Street & First Street).
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 30 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 and a one-night stay at Harbor Front Inn.
Meanwhile, the Harbor Front Inn, The Menhaden, and 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, and 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 and the Greenport BID this year to continue to build the stroll into a tradition for years to come.”
Event highlights include the Greenport Antique Carousel, which will be open with free rides for children under 12, sponsored by The Friends of Mitchell Park. The Local Artisan Night Market at Harbor Front Inn and the Menhaden lobbies features handmade gifts and holidaywares, along with offerings at Little Creek’s Hold Fast Studio on Main Street. Featured artisans include Sasha Samuel Jewelry, Nofo Style, Disset Chocolate, Red Earth Herbals, NFAC artists Jackie Dandelion, Paul Brooke, Katie Kooks, Wild Muse, Bridge & Sound, and more.
Live music and caroling will fill the village, with performances by the First Baptist Church of Greenport Carolers and Dave Berson. The GHS Acapella group begins singing at Harbor Front at 6 PM, then visits multiple businesses along Front and Main Streets until 7 PM. The Greenport High School Jazz Jam will pop up at The Hold Fast Studio from 5 to 6 PM. A live holiday dance show will take place at the roped-off Street Stage by Inspire Dance Center at 5:30 PM and 6:30 PM.
Festive décor and photo opportunities will be available along Front and Main Streets, with the road closed from 3rd Street (Menhaden) to 1st Street (Aldo’s), featuring decorated fire trucks, a tractor courtesy of Sepnoski Farms, and a boat from The East End Seaport Museum. Santa will be available for photos at the Old Schoolhouse, with Madison Fender Photography capturing the moments.
The Village Schoolhouse will be open for crafts from C.A.S.T., a food drive, and storytime with Nina Keller, Children’s Librarian at Floyd Memorial Library. The Village Blacksmith will also be open, offering demonstrations with Tom, the village blacksmith. The Stirling Historical Society and the Ireland House will be open from 5 to 8 PM.
Fire pits along the Front Street closure will keep visitors warm during the stroll, sponsored by American Beech in partnership with the Greenport Fire Department. Outside of Aldo’s Coffee Company, enjoy Cops & Cocoa and view a decorated holiday police car provided by the Southold Town Police Department.
For those wishing to make a full weekend of it, Harbor Front Inn is offering a limited-time “Holiday Suite” experience, a cozy, festive getaway right in the heart of Greenport Village. The Terrace Suite will be decked out for the season with twinkling lights, plush throws, holiday pillows, and even a petite Christmas tree to set the scene. The booking includes a festive in-room décor and mini tree, popcorn, and hot cocoa amenity kit for your holiday movie marathons, late checkout (based on availability), and a waived amenity fee.