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Winter whimsy takes over Southold on Saturday

While it’s easy to gloat about the never-ending cold, a tried-and-true cure to the winter blues is to get outside and embrace it. 

Coming off another weekend snowfall, Southold WinterFest could not be timed more perfectly, packed with community, entertainment and a frenzy of free samples. On Feb. 21, from 10 a.m. to 3 p.m., swing by Southold’s Main Road between Hortons Lane and IGA for the fifth annual seasonal celebration.

Jennifer Del Vaglio, chairperson of Southold WinterFest and the small team of organizers for the event, started planning in September. In its half a decade, Del Vaglio says the day has evolved exponentially, starting with just a handful of vendors and is now up to 60 with a waitlist. 

“It’s been really fun to watch it grow,” says Del Vaglio. “It just kind of started out as a little pipe dream, something that we thought would be really great for the community. It was twofold really — to generate business in a really quiet time of year for the North Fork, but also something fun for all of our local residents to come out of the house for the day with the kids and give everybody something to do when there’s not quite as much to do in this area in the off season.”

This year, Main Road will feature ice sculptures from Apple Ice, face painters, jugglers, line dancing and shopping at local storefronts. 

Photos courtesy of Southold WinterFest Committee

New additions to the annual lineup include a climbing trailer with 40 feet of climbing walls and obstacle courses for kids, plus 45-minute shows from Uncle Tony’s Reptile Show at the Southold Library

One return attraction will be the Southold Village Green Gazebo snow globe. And bring your appetite, as there will be samples from food vendors like  Southold Fish MarketKK’s the FarmDisset ChocolateFields of DoughTommy PicklesBeleza BBQ and Hoffman Bread. 

At Southold Historical Museum, experience historic campus tours, handmade crafts, hot chocolate, a snow machine play area and snacks from North Fork Flour Shoppe

On the entertainment side of things, WinterFest goers are in for a treat with music from Points EastJulia GraceNorth Fork Dirt BandEastern Long Island Old Time Jam BandWantagh American Legion Pipe BandHoodoo Loungers and Roth and Fuhr Men Band spread throughout the event at the Southold Village Green Gazebo, Southold Historical Museum, First Presbyterian Church of SoutholdNorth Fork Taps & Corks and along Main Road.

Photos courtesy of Southold WinterFest Committee

North Fork Community Theatre will preview its March-opening show, 1776: The Musical

And the fun doesn’t have to end after the Norman Rockwell-esque event; bring home the festivities in the form of a raffle basket packed with community goodies.

“It’s really the whole experience that everyone enjoys,” says Del Vaglio. 

Plan your day with the schedule and learn more at Southold WinterFest’s Facebook page


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