Southold’s 3rd Annual WinterFest is what’s to do this weekend

Bundle your fam up and head to downtown Southold this weekend on Saturday, Feb. 17, from 10 a.m. until 3 p.m. for a day of small-town fun with WinterFest.

There, you’ll find local businesses and residents celebrating the season while providing entertainment, shopping, food (hello, free, freshly-shucked Littleneck clams compliments of Southold Fish Market!), drinks, crafts, live and DJ music, and more spilling onto Main Road in a street festival-style outdoor event. Outdoor highlights include ice sculpting, face painting, hair tinseling, glitter tattoos, and a caricature artist.

Some local businesses are opening their doors with special offerings coinciding with the festival. While some happenings will be geared toward adults like The Giving Room’s Gallery Show from 12 - 5 p.m., featuring work from local artists, there will also be many family-friendly and kid-centric offerings happening throughout the day. Here are some of our favorites that are great for your petite crew.

Sweet Tunes and Treats at CAST

The Center for Advocacy, Support and Transformation (CAST) has a day of free family-friendly programming planned inside their building — a perfect way to warm up. Kicking it off at 10 a.m. with cupcake decorating in the CAST kitchen, attendees are invited to decorate (and enjoy!) cupcakes. Then, from 10:30 to 11:30 a.m., feast your ears on a super fun, bilingual live performance by Lucy Kalantari & the Jazz Cats. Later in the day, from 1 to 2:30 p.m., head back to CAST for another live performance, this time by the Caribbean Vibe Steel Drum Band, whose tunes will transport you somewhere warm! Lite bites and refreshments will be provided by CAST’s North Fork Culinary Program throughout the day.

A Frosty Favorite at The Country Corner Cafe

The Country Corner Cafe will serve free ice cream cones during WinterFest, thanks to owner Martin and his staff. While you’re there, dig into cozy comfort food that’s sure to warm you up like their amazing homemade soups.

Cotton Candy and Crafts at the Southold Free Library

Spot the cotton candy machine on Main Road at the Southold Free Library and pick up your craft voucher. Then, head into the library where the voucher can be redeemed for a DIY snowman craft with a special treat inside.