Posted on 2/2/2026 by Stacy Carlson

Oakland Winter Fest

Oakland Winter Fest is a favorite event that offers plenty of frosty fun! 

The streets of Oakland's charming historic district come alive with creativity and community spirit. You can enjoy dazzling ice sculptures, lots of family activities, a wine walk, sleigh rides, and plenty of local charm.

Oakland Winter Fest is held annually, and it takes place on the Saturday of President's Day weekend. When you are visiting Deep Creek Lake for the weekend, the festival is a great way to celebrate the season.

Ice Sculptures Throughout Downtown Oakland

The centerpiece of Oakland Winter Fest is the collection of beautifully carved ice sculptures displayed throughout downtown. Large blocks of ice are transformed into detailed works of art that line the sidewalks and storefronts of the Oakland Arts & Entertainment District.

As you stroll through town, you can admire a variety of creative designs and take photos with your favorite sculptures. The displays turn downtown Oakland into a winter art gallery and create a magical atmosphere!

Horse-drawn Sleigh Rides

One of the most memorable experiences at Oakland Winter Fest is the opportunity to enjoy a horse-drawn sleigh ride. The rides offer a nostalgic way to take in the sights of the festival while enjoying the crisp winter air.

Families especially love this activity, as it adds a classic winter feel to the day.

Winter Farmers Market

The Oakland Winter Fest Farmers Market at the Mountain Fresh Pavilion is another highlight of the event. Local vendors gather downtown to offer a variety of fresh foods, handmade goods, and locally produced products.

You can browse items like baked goods, artisan crafts, locally grown foods, and specialty products while supporting small businesses from the Garrett County area. It’s a great place to pick up unique gifts or tasty treats while exploring the festival.

Winter Wine Walk

For adults attending Oakland Winter Fest, the Wine Walk is a popular way to experience the event. Participants can sample wines while checking out the ice sculptures and visiting participating businesses. The Wine Walk is a fun way to explore Oakland’s shops and restaurants.

A Perfect Addition to a Deep Creek Lake Winter Getaway

Located just minutes from Timber Rock Village and Deep Creek Lake, Oakland Winter Fest is an easy addition to any winter trip. It's a great option for families or for the non-skiers in your group.

With its beautiful ice sculptures, sleigh rides, local vendors, and lively downtown setting, Oakland Winter Fest has become a beloved winter tradition.

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