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Southold WinterFest is at no cost to all residents and visitors. It includes live entertainment, free food and beverage samples, fun activities for adults and children, special events, as well as free prizes and gift raffles. Restaurant, pub and winery favorites such as Maroni Cuisine, Latin Fuzion, North Fork Taps and Corks, Eastern Front Brewery, North Fork Roasting Co., Pindar Vineyards, Southold General, and The Giving Room will offer free beverage and food samples. 


Activities include a DJ, shows at CAST with the Caribbean Vibe Steel Drum Band and Lucy Kalantari and the Jazz Cats. The popular Foster Europe Band and the talented Jay Shepard Band will be playing at the Village Green. There will be main stage events at the First Presbyterian Church with Lady T’s Highway Dancers and the Hoodoo Loungers band. The event includes cha-cha and swing dance lesson, a caricaturist, crafting workshops, cupcake decorating, free drawings for gift baskets and jewelry, face painting, glitter tattooing, flame juggling, hair tinseling, ice sculpting, a popcorn station, a snow making machine and even a WinterFest “Selfie” Station. Visit SoutholdWinterfest on Facebook for updates.