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5 Favorite Oakland Winter Fest Activities

Oakland Winter Fest Ice Carving

Oakland Winter Fest is held the Saturday 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. For the second year, you can buy a $15 ticket for the Wine Walk. You can taste approximately 12 different wines, which will be available at a number of locations throughout the town.

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.

Oakland Winter Fest

Take a horse drawn sleigh ride. 

Take 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 clothes at Rudy’s, pick up some classic vinyl at Flipside Sounds or shop for treasures made by local artists at The Gallery Shop. Oakland Mercantile is a new spot where you will find lots of unique items. Plus, you can walk to three different antique stores!

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, grab lunch and check out cool retro decor at Alder Street Diner or visit Dottie’s Soda Fountain in Englander’s. If you haven’t been to Sipside Lounge or The Vagabond Taproom, I suggest checking them out!

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