Image by Jeremy Garretson
About the Stroll
The 2nd Annual Greenport Holiday Stroll & Harbor Front Night Market Returns!
Join us for a magical evening throughout Front & Main Streets (Carpenter St. & First St.) as over 45 local businesses, artists, and community partners come together for a festive night of shopping, music, treats, art, and holiday cheer.
Enjoy street closure from 3rd St. (Special thanks to Greenport Village, Greenport BID, Southold PD, & Greenport Fire Department
Start your night at The Harbor Front Inn lobby to check in and pick up your event booklet: complete with a village map, list of participants, and a 30-stop Holiday Bingo Card. Complete your card for a chance to win a local goodie bag and a one-night stay at Harbor Front Inn!
Image by Jeremy Garretson
Event Highlights
Check in at the Harbor Front Inn lobby to pick up your event booklet — complete with a map, a list of participating businesses, and a holiday bingo card. Stroll to visit shops, galleries, and restaurants offering festive cocktails, pop-up vendors, interactive photo ops, and sparkling window displays.
· 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 holiday wares, 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, & 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 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 Company & 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!
Sip, Stroll, Stay
A Holiday Escape At The Harbor Front Inn
Celebrate the magic of the season in the heart of Greenport Village with our Sip, Stroll, Stay package—created especially for the Greenport Holiday Stroll & Harbor Front Night Market.
Your Stay Includes:
Exclusive Savings: Enjoy 10% off a one-night stay, or 20% off when you stay the full weekend.
Hot Cocoa Bar: Warm up in our lobby from 5–8 PM during the Stroll with a cup of cocoa, festive toppings, and plenty of holiday cheer.
Holiday Stroll Bingo Card: Explore downtown Greenport’s shops, galleries, and twinkling stops with a playful seasonal guide.
Whether you’re sipping cocoa, shopping under the lights, or relaxing after the festivities, The Harbor Front Inn is your front-row seat to Greenport’s most charming winter weekend—steps from the market, restaurants, and waterfront.
Stay Dates: December 19 - December 21, 2025
Other Greenport hotels including The Menhaden & American Beech will be offering discounted rates & special amenities during the Stroll.
Grateful for Our Incredible Sponsors
THE FLOTTERON FAMILY
THE WEATHERED BARN
AMERICAN BEECH
LIANE BURGER & FAMILY
THE ANDY FOUNDATION
HARBOR PET
FIRST & SOUTH
HARBOR FRONT INN
LITTLE CREEK OYSTERS
NORTH FORK ARTS CENTER
MICHAEL ARON
FRONT STREET STATION
ALDOS COFFEE COMPANY
