Holiday shopping doesn’t have to be stressful thanks to two upcoming events on the North Fork. Walk through winter wonderlands in Southold and Greenport and check off those last few gifts on your list while enjoying festive treats, entertainment and deals at local businesses.
On Dec. 12 from 5 to 8 p.m. the Southold Holiday Evening Shopping Stroll, featuring 25 Main Road locations, will be back for its third year.
“It’s really nice to shop at night with all the lights twinkling,” says touchGOODS owner, Norine Pennachia. “It feels festive and we find that it’s a great opportunity for last minute shoppers.”
For home products and gifts along the stroll visit touchGOODS, The Bellwether, Fez & Ivy, White Flower Farmhouse, White Flower Garden, One For All Gifts, Forked Road Press, Nicolette’s for the Home, J. McLaughlin, Party Animal North Fork, Pearl on Main, Arni Paperie, Rowan Craft Boutique and Save the Container.
If you’d like to grab a bite to eat or a drink along the way, stop at Southold General, Latin Fuzion, Bogey’s, Maroni Cuisine or North Fork Roasting Co.
To connect with Southold’s community organizations, drop into The Giving Room, CAST and Southold Historical Museum.
And lastly, pop into the real estate and professional service businesses on the list like Signature Premier Properties, The Agency North Fork and Albertson Realty.






Pick up a postcard from any participating businesses to stamp at each stop. No purchase is required for a stamp at most locations, and shoppers can leave their postcard at the final shopping destination they visit to be entered into the holiday raffle, featuring gifts donated by participating shops.
To keep the festivities going, on Dec. 19 from 5 to 8 p.m. Harbor Front Inn and North Fork Art Collective are putting on the second annual Greenport Holiday Stroll and Harbor Front Night Market.
Stop into Harbor Front Inn to pick up a booklet with a map, the list of over 45 participating businesses and a holiday bingo card with 24 stops across the village. By completing the bingo card, be entered to win a local business goodie bag and a one-night stay at Harbor Front Inn.
Front Street, from First to Third Street, will be closed off to cars and Main Street will be decorated with giant candy canes, fire pits and other holiday props provided by the community with most business opening doors for shopping and stopping in. The Greenport Village Blacksmith will also put on demonstrations for passersby.
Plus, get artisanal gifts from Sasha Samuel Jewelry, Nofo Style, Disset Chocolate, North Fork Art Collective creatives and other vendors in the pop-up markets in Harbor Front Inn, The Menhaden and The Hold Fast Studio, Little Creek Oyster’s extension. Enjoy live music and performances from the First Baptist Church of Greenport Carolers, David Berson, the Greenport High School Acapella Club and the Greenport High School Jazz Band, plus seasonal snacks and cocktails at participating businesses.





Kids 12 and under are welcome to ride the Greenport carousel for free, sponsored by Friends of Mitchell Park.
Food drive donations will be accepted at the CAST village schoolhouse, where kids can also find crafts, Floyd Memorial children’s librarian Nina Keller reading for story time and photos with Santa shot by Madison Fender.
“The Holiday Stroll is about coming together as a community and supporting the small businesses and artists that make Greenport so special,” says Kara Hoblin, director of guest culture and experiences at the Harbor Front Inn and founder of The North Fork Art Collective.
Make it a weekend by booking one of The Harbor Front Inn’s packages, or take advantage of special rates at The Menhaden and American Beech, perfect for continuing the holiday fun.