5 Favorite Oakland Winter Fest Activities

Oakland Winter Fest Ice Carving

Oakland Winter Fest is held the Saturday and Sunday of President’s Day weekend each year. It is a great way to celebrate the season with friends and family. You can stroll through the historic downtown as you enjoy delicious food and fun activities.

I picked out 5 of my favorite Oakland Winter Fest activities that you absolutely don’t want to miss!

Oakland Winter Fest

Watch Master Ice Carver Bill Sandusky create beautiful sculptures.

Each year, Bill travels from Erie, PA to create more than 30 unique ice carvings that decorate the sidewalks. You can watch his demonstrations or check out one of the interactive sculptures like the ice bowling alley that is a big hit with the kids!

Oakland Winter Fest

Take a horse drawn sleigh ride. 

Pleasant Valley Dream Rides is on hand to take you on a free sleigh ride through the streets of this picturesque small town. It is a classic winter experience that you will always remember.

Oakland Winter Fest

Get a local history lesson.

When you need to warm up, step inside the Garrett County Historical Museum, the Garrett County Transportation Museum or the Oakland B&O Railroad Museum. Each one features interesting displays that will take you back in time. See what life what like throughout Garrett County’s history.


You can browse for clothes at Rudy’s, one-of-a-kind accessories at the Chic Shack, or treasures made by local artists at The Gallery Shop. Plus, you can walk to three different antique stores and craft vendors are also on-hand!

Oakland Winter Fest

Enjoy yummy food from cafes, restaurants & vendors.

Try one of the sweet treats at Cornish Cafe with a cup of hot coffee or visit Dottie’s Soda Fountain in Englander’s. It is an old-school spot where you can sit a lunch counter and order one of their famous milkshakes.

Experience the charm of Oakland Winter Fest with your favorite people. It is truly “A Great Small Town”!

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