WinterFest to Return to Southold

Pictured Above: The Rob Europe Band will play on the Southold Village Green from 11 a.m. to 2 p.m.

Downtown Southold will come alive again this President’s Day Weekend with the second annual WinterFest along the Main Road on Saturday, Feb. 18 from 10 a.m. to 4 p.m.

The event, free to all residents and visitors, will have many exhibits featuring local businesses and organizations. It will also include live entertainment, free food and beverages, activities for adults and children, special events and prizes.

“In 2021, we started talking about developing a winter event to support our local businesses and provide something fun and exciting for both visitors and Southold Town residents,” said Jack Malley, chairperson of the Southold Town Economic Development Committee. In 2022 we created the template for this event, which attracted over 30 organizations and hundreds of visitors. That enabled us to create a solid launching pad for the 2023 event. We expect participation to double this year. An experienced operations team is in place and we already have participation commitments from many more local businesses and organizations.”

Here’s the schedule of events:

First Presbyterian Church

11:00am-3:00pm Fire pits, s’mores, and stuffed potatoes – Sponsored by First Presbyterian Church

11:45am-1:45pm Lady T DJ music and line dancing

10:00am-4:00pm No Dogs Left Behind

Nicolette’s for the Home

In-store discounts

Taps and Corks

12:00pm-4:00pm – Free warm beverage samples 

2:00pm-4:00pm – Rothman Band 

Latin Fusion

Free chili and soup samples

One for all Gifts

Free popcorn and chocolate samples

South Parking Lot

10:00am-4:00pm DJ at parking lot across from library

10:00am-4:00pm Face Painting and Hair tinsel – provided by Boces ($)

10:00am -4:00pm Ice Sculpture – Sponsored by East End Pool King

12:00pm-3:0pm Girl Scouts

Winter Festival Committee Table

NYU Langone

PTA Table

Chris Hamilton Photography

Southold Library – main road parking area

11:00am-1:00pm Southold Library Empowering Discovery SLED 

CAST – sponsoring the following:

10:30am Sammy and Tudies Magic Circus 

11:15am Sammy and Tudies plate spooning and balloon making on stage

Cookie decorating in the Cast Kitchen 

2:00pm Lite Bites from North Fork Culinary Program 

3:00pm Juana Cala Flamenco Dancing and Music Flamenco 

Maroni Southold

Free Chocolate mousse cupcakes with toasted marshmallow topping

Petty’s Blacksmith Shop – 340 Mechanic Street 

10:00am-2:00pm– Tours and historical Display

Southold Historical Museum 

1:00pm-4:00pm – tours and children’s activities 

Southold Indian Museum

Southold Town Hall Annex 

East Marion Community Association

Sea-Tow Foundation

Southold Peconic Civic Association

First Universalist Church of Southold

Kolb Heating and Cooling

SINY Dermatology

Alison Shelby – crafts

11:00am-3:00pm Caricaturist

Village Green (gazebo)

10:00am-4:00pm Southold Fish Market

10:00am-4:00pm create telescope like viewers and arrange stars into constellations on magnetic boards – Sponsored by Peconic Community School

11:00am-2:00pm Rob Europe BandSponsored by Economic Development Committee

11:00am-3:00pm Balloon ArtistSponsored by New Vine Wine Tour and Luxury Transporter

12:00pm-4:00pm Custer Institute and Observatory – Solar gazing

Eastern Front Brewing Co.

Pindar Vineyards – wine tasting

Vintage Mattituck Wine and Spirits – giveaways

Satnick Jewelers – free jewelry cleaning and discounted jewelry 

Rotary Club – raffles and giveaways – free hot cider

Southold Youth Group and Southold Recreation

Country Corner Café

free scoop of ice cream – mention the Southold Winterfest

North Fork Roasting Company

Free samples of Chai Latte

Beth Young

Beth Young has been covering the East End since the 1990s. In her spare time, she runs around the block, tinkers with bicycles, tries not to drown in the Peconic Bay and hopes to grow the perfect tomato. You can send her a message at

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