Greenport has set the date for its third Holiday Stroll and Harbor Front Night Market: Friday, December 18, from 5 to 8 p.m. More than 45 local businesses, artists and community groups are taking part, Front Street will be closed to cars from Third Street to First Street, and fire pits will line the road so people can warm up between shops.

Start at the Harbor Front Inn

The night begins in the lobby of the Harbor Front Inn at 209 Front Street, where visitors check in and pick up an event booklet. It holds a village map, the list of participating businesses, their holiday specials and a 30-stop Holiday Bingo Card. A completed card is entered in a drawing for a local goodie bag and a one-night stay at the inn.

From there, the stroll runs through the shops, galleries and restaurants of the village, with holiday cocktails, pop-up vendors, photo spots and decorated windows along Front and Main Streets.

What is on the route

  • The Greenport Antique Carousel in Mitchell Park opens with free rides for children under 12, sponsored by the Friends of Mitchell Park.
  • A local artisan night market fills the lobbies of the Harbor Front Inn and The Menhaden, plus Little Creek's Hold Fast Studio on Main Street. The featured makers include Sasha Samuel Jewelry, Nofo Style, Disset Chocolate, Red Earth Herbals and NFAC artists.
  • Carols and live music come from the First Baptist Church of Greenport Carolers and Dave Berson. The Greenport High School a cappella group starts at the Harbor Front at 6 p.m. and works its way down Front and Main until 7.
  • A street stage hosts holiday dance performances by Inspire Dance Center at 5:30 and 6:30 p.m.
  • Santa is at the Old Schoolhouse for photos with Madison Fender Photography. The Village Schoolhouse also has crafts from C.A.S.T., a food drive, and a story time with Nina Keller, children's librarian at Floyd Memorial Library.
  • The village blacksmith has the forge open for demonstrations.
  • Cops and Cocoa sets up outside Aldo's Coffee Company, alongside a decorated Southold Town Police car.
  • The Stirling Historical Society and the Ireland House are open from 5 to 8 p.m.

The closed stretch of Front Street, from The Menhaden at Third Street to Aldo's at First Street, becomes a photo row of its own, with decorated fire trucks, a tractor from Sepenoski Farms and a boat from the East End Seaport Museum. The fire pits are sponsored by American Beech in partnership with the Greenport Fire Department.

Who makes it happen

The stroll is organized with the help of the Village of Greenport, the Greenport Business Improvement District, the Southold Town Police Department and the Greenport Fire Department. This year's is the third.

If you go

The Greenport Holiday Stroll is Friday, December 18, 2026, from 5 to 8 p.m., throughout Greenport Village, starting at the Harbor Front Inn, 209 Front Street. The Harbor Front Inn is offering a Sip, Stroll, Stay package for visitors who want to make a night of it, and the stroll's website has the participant map.

Sources