Second Annual Greenport Holiday Stroll Set for Dec. 19

The Greenport Holiday Stroll will return Dec. 19, offering an evening of late-night shopping, seasonal treats and village-wide festivities aimed at boosting business during the quiet winter months.

The event began last year when organizer Kara Hoblin, an artist and founder of the North Fork Art Collective, sought to create a livelier atmosphere downtown after hearing from local shop owners.

“I started it last year to create the Greenport Hallmark movie of my dreams,” Hoblin said. “It’s so quiet this time of year. We have a great local community, and I really wanted to create some sort of activation in the village.”

Last year’s stroll featured about 30 businesses. This year, Hoblin said participation has grown to more than 45 and is still increasing. Shops, galleries and restaurants will stay open from 5 to 8 p.m., offering a mix of discounts, extended hours and holiday-themed specials. Examples include 10% off at the Weathered Barn, 20% off at Harbor Pet, boozy hot chocolate at Aldo’s Coffee Company, and extended happy hour at Noah’s.

“It’s really up to each business,” Hoblin said. “As long as it’s some kind of holiday activation, a special, a discount — something fun.”

A major new addition this year is a coordinated partnership with the Village of Greenport and the Business Improvement District, allowing for the closure of the stretch of street between The Menhaden and Aldo’s. The space will be outfitted with propane fire pits supplied by the fire department, outdoor furniture donated by American Beech, and decorative installations.

“We’ll have these little warming fire pit activations throughout the closed street,” Hoblin said. “The East End Seaport Museum is decorating a boat to display in the street, the fire department will have decorated trucks with characters, and Southold PD is doing a decorated car and a ‘cops and cocoa’ station.”

The Inspired Dance Company will perform two holiday routines, and several local churches have signed on to provide roving carolers.

The family-friendly format also returns. Visitors will check in at the Harbor Front Inn to pick up an event booklet, map and bingo card featuring participating businesses. Those who collect the required number of stamps will be entered to win a one-night stay at the Harbor Front Inn and a gift basket from local shops.

“Families loved it last year,” Hoblin said. “The kids really got into the bingo card.”

Mitchell Park will also take on a larger role. The village is opening the carousel from 5 to 8 p.m., and the nonprofit Friends of Mitchell Park will cover the cost of rides for children under 12. Hoblin said she is also fundraising for additional large-scale decorations and inflatables to enhance the park’s holiday atmosphere.

The village blacksmith shop will open for demonstrations, the village schoolhouse will host Santa and community crafts through CAST, and several indoor spaces will include pop-up vendor markets — including at Harbor Front Inn, The Menhaden, and a Little Creek–affiliated space on Carpenter Street.

Hoblin said her long-term goal is to build the stroll into an annual tradition that encourages families — and eventually visitors — to make a full weekend out of Greenport’s holiday offerings.

“My hope is that it really becomes a Greenport tradition,” she said.

More information is available on Instagram at @greenportholidaystroll.