Greenport’s Holiday Stroll Returns With Cheer, Charm, and a Chance To Win

Last December, just as Front Street businesses began welcoming people in for the inaugural Greenport Holiday Stroll, a light snow began to fall. The unexpected winter’s welcome was a magical moment that organizer Kara Hoblin still to this day cannot believe happened.

“It was so magical … it was just this tiny little flurry,” she said. “I thought, ‘That’s a good sign.’”

Hoblin, who is an artist, the founder the North Fork Art Collective, and the director of guest culture at Sound View and the Harbor Front Inn, put the Greenport Holiday Stroll together last year after speaking with business owners who said that town was a little quiet. She had already organized a holiday market at Sound View in conjunction with the art collective since 2017, so it made sense to bring it to Harbor Front and extend the festivities outward to surrounding businesses, she said.

She looked to the successful Southold Holiday Stroll and picked the brain of Norine Pennachia of touchGOODS, who has been involved in organizing that stroll for years.

From there, Hoblin was able to get nearly two dozen businesses to keep their stores open late, from 5 to 8 p.m., to welcome strollers. Everyone was given a bingo card at the start — at Harbor Front, where there was a night market of vendors — to get stamps from participating storefronts, as well as deals, discounts, drinks and treats.

Last year, for instance, the Weathered Barn had mulled cider and biscotti for shoppers and offered a free star ornament for those who spent over $25. Barbara Fisher Home gave away organic essential oil rollerballs by Flora Beauty with purchases of over $50. Aldo’s Coffee Company had boozy hot chocolate and festive drinks for the occasion and Clarke’s Garden had $20 specials, Ali Katz cookies, Belgian chocolate samples and sales that started at $10. Harbor Pet had customers stuff stockings and gave a 20 percent discount off everything that could fit, as well as pup cups with purchases.

At the end of their journeys, strollers returned their completed bingo cards to be entered to win a one-night stay at the Harbor Front Inn and goodies from participating vendors.

Hoblin said she saw every age turn out among the approximately 100 strollers, from kids to the elderly.

“Families and their kids really got into it,” she said. “And you don’t have to actually purchase anything to get a stamp.”

According to Kimberly Loper, the owner of Harbor Pet and a board member of the Greenport Business Improvement District, “It was such a hit!”

“The bingo card made it fun for everyone to visit different shops, which brought in a ton of foot traffic and gave our in-store sales a great boost,” she said. “We received many new customers because of the bingo cards. It was a busy day for all of us and really helped build connections with new and returning customers.”

The stroll, which returns this year on December 19, from 5 to 8 p.m., will bring back the bingo card, as well as vendors and artisans inside the Harbor Front Inn and The Menhaden, snacks and drinks along the way, and another chance to win a stay at the inn and more prizes from Greenport businesses. According to Hoblin, other businesses participating in this year’s stroll include Little Creek Oysters, the Weathered Barn, Harbor Pet, the North Fork Art Collective, Encanto Crepes, One Love Beach, Aldo’s Coffee Company and First and South.

The Harbor Front Inn lobby will serve as the central hub for all things for the stroll, where visitors can pick up event booklets, bingo cards and information about the festivities. The Harbor Front Inn and The Menhaden will also present a curated Night Market, showcasing local artisans, makers, and small businesses offering handcrafted gifts and holiday treasures. Throughout the village, shops, galleries, and restaurants will keep their doors open late, inviting guests to enjoy festive cocktails, pop-up vendors, interactive photo ops and glittering holiday window displays.

Hoblin said many restaurants last year had specials to celebrate as well, and she expects the same this time around. She hopes this year that she’s able to work with the town to close off a section of Front Street so the strollers can have more room.

Like last year, it is free to participate.

“You don’t have to necessarily buy something, so I feel like that allows people who maybe don’t have the funds also to participate in something fun,” Hoblin said. “And I love the holidays, and Greenport has such beautiful lights. It just feels like it’s nice to see the village activated in the cold months.”