Family-friendly WinterFest returns to Southold on Feb. 21 with more offerings for kids than ever before
Bundle up and head to Main Road, Southold, on Saturday, Feb. 21, from 10 a.m. until 3 p.m. for a big day of small-town fun at the fifth annual WinterFest.
The festival will feature community-driven fun for all with over 50 exhibits of food and beverage sampling, performances by local bands, musicians, and a live DJ, firepits with s’mores, baked potatoes, discounts from local shops, special events and prizes, and plenty for kids of all ages.
Member of the Southold Economic Development Committee, WinterFest Founder, and Owner of East End Pool King, Jennifer Del Vaglio, shared some of this year’s family-friendly offerings, “We’ll have sandcrafts, paper airplane making, library crafts, inflatable large snow globe great for photos, face painting, roaming characters, a stilt walker performing magic shows, and the star of the show: ice carving by Apple Ice.”
This year, Southold Free Library will be offering snowmen and paper mitten crafts; there will be sand art and hot chocolate at the First Presbyterian Church of Southold, as well as crafts, food, and entertainment at the Southold Historical Museum, plus some exciting new additions.
“Some new special [family-friendly] treats for this year include pony rides, a snow machine and friendly snowball fight, Uncle Tony’s Reptile show, and an indoor climbing wall and obstacle course,” Jennifer told us.
This year’s festival entertainment includes live performances by Points East, Julia Grace, and the North Fork Dirt Band in the Southold Village Green gazebo, the Eastern Long Island Old Time Jam Band at the Southold Historicall Museum, the Wantagh American Legion Pipe band on Main Road, the Hoodoo Loungers at the First Presbyerterian Church of Southold, as well as Roth, Fuhr Men Band and Julia Grace at North Fork Taps and Corks, and more. Visit here for the complete schedule, including performance times.
WinterFest has always had the goal of generating business for our local community during winter while giving residents something fun to do, and encouraging new visitors to experience the charm of Southold. Its fifth year of Winterfest will be no different.
“It is always just a magical day with smiles on everyone's faces,” said Jennifer. “The town is alive and thriving, giving a true sense of small-town community and charm with plenty of shops and restaurants to pop in and out to stay warm.”
The Southold Town Economic Development Committee, along with CAST, the Southold Free Library, the Cutchogue New Suffolk Free Library, the First Presbyterian Church, the Southold Historical Museum, and other local merchants, have worked hard to support this event, building it into the success it is today.
WinterFest is free to attend and welcomes all. A raindate is scheduled for Sunday, February 22, should it be needed.

