The beloved Oakland Winter Fest will land on Valentine’s Day in 2026!
Bundle up and join the Oakland Arts & Entertainment District on Saturday, February 14th, from 11 am to 4 pm for the annual celebration, filled with fun for the whole family!
This year’s theme celebrates love in its many forms, with ice sculptures of hearts, love birds, and cherubs; games and interactive sculptures for family entertainment; and mouthwatering treats by local bakers. Also, don’t miss out on the chili cook-off hosted by St. Peter’s Catholic Church!
Guests will find plenty to enjoy, with activities scattered throughout the downtown Oakland area. Live musical performances create a romantic feeling, while local shops offer exclusive Winter Fest specials, perfect for a little treasure-hunting. Don’t miss multiple photo-opportunities, including installed artwork in Banker’s Alley and various themed cut-outs and romantic backdrops. Also, locally made breads, chocolates, and cheeses will delight your tastebuds!
Winter Fest Wine Walk
For those 21 and older, don’t miss the ever-popular Wine Walk! You’ll receive a wristband, punch card, and tasting cup to sample a curated selection of wines, located at stops throughout the district. Bring a friend or Valentine and toast at each of the locations in the Oakland A&E!
Early bird tickets are $25, to be purchased by 5:00 pm, February 13th. On the day of the event, tickets are $35, so don’t wait! A limited number of tickets are available, so snag yours today to avoid missing out! Buy tickets online (https://garrettcountyartscouncil.ticketspice.com/2026-winter-fest-wine-walk). Remember, all Wine Walk participants must be 21 or older and present a valid ID at check-in.
Winter Fest 2026 promises a day packed with joy, camaraderie, and plenty of frosty fun! This event is made possible through the collaboration of the Garrett County Arts Council, Town of Oakland, and the Oakland Arts & Entertainment District’s community partners. Whether you’re discovering unique handmade gifts, enjoying music, or toasting to your Valentine, you’ll enjoy this winter celebration that will warm your heart!
Written by Garrett County Arts Council.