10 Best Things to Do in Oakland, Maryland

By VacationIdea Staff on June 19, 2023 - Updated

Town of Oakland, Maryland

Oakland is a small town in the west-central part of Garrett County, Maryland. Oakland is located near Deep Creek Lake and only few miles from the source of the Potomac River. Oakland Historic District has a number of beautifully restored Victorian buildings, which today house galleries, pharmacy, a library and fashionable boutiques.

Swallow Falls State Park is located on the bank of the Youghiogheny River, and is known as the location of the 53-foot Muddy Creek Falls, the highest falls in Maryland.

1. Swallow Falls State Park

Swallow Falls State Park is located on the west bank of the Youghiogheny River, about nine miles from Oakland, Garrett County, Maryland. The park is known as the location of Maryland's highest free-falling waterfall, the 53-foot Muddy Creek Falls. There is also a number of smaller waterfalls on the Youghiogheny River and Tolivar Creek. The park is famous for its stand of old growth hemlock trees. Some of them are more than 300 years old, and are part of the last stand of its kind in Maryland. The park has 65 campsites, a lovely picnic area with a pavilion and kids’ playground. There is a mile-long hiking trail through the old growth hemlock forest. Another, a 5.5-mile long hiking and biking trail, connects the Swallow Falls park with Herrington Manor State Park.

2470 Maple Glade Rd, Oakland, MD 21550, Phone: 301-387-6938

2. The Oakland B&O Railroad Museum, Oakland, Maryland

The Oakland B&O Railroad Museum in Oakland, Maryland is located inside the 1884 train station, an exquisite Queen Anne style structure designed by E. Francis Baldwin. With its circular tower, a bell-shaped roof, half-timbered gables, and fish-scale shingles, the station is considered one of the most significant historic depots in the country. The building was completely renovated in the early 1990’s by a group of local citizens. The Museum contains a number of local artifacts from the Garret County’s rich rail history. The museum organizes frequent rotating exhibits with artifacts from the B&O Railroad Museum in Baltimore. The Station is also an educational center for the county, hosting guest speakers who detailed the rich history and importance of the railroad to Garrett County and the region in general.

117 E Liberty St, Oakland, MD 21550, Phone: 301-334-3204

3. Things to Do Near Me: Garrett County Historical Museum, Oakland, MD

The Garrett County Historical Society combines different aspects of the history of Garrett County into three museums with diverse displays and presentations. The Garrett County Historical Museum features a variety of artifacts that portray the history of generations of Garrett County residents. The Museum houses a range of exhibits related to the history of the land, the founding of Garrett County and the Garrett County citizens’ way of life for from years past. The museum contains a replica of a B&O train called "Little Maryland." The train was built by Stephen Pagenhart when he was only 16 years old. The train was featured in the Chicago World's Fair in 1893. The Exhibitions cover nine rooms, each presenting a specific era in the history of Garrett County

107 S 2nd St, Oakland, Maryland 21550, Phone: 301-334-3226

4. Things to Do Near Me: Brenda's Pizzeria, Oakland, Maryland

Brenda’s is a bright and spacious New York Style Pizzeria located on the lakefront at Trader's Landing, along Rt. 219. Brenda’s offers a wide range of entrée favorites and a few interesting surprises such as seafood, vegetarian dishes and gluten-free pasta. The dough for pizzas, calzones and breadsticks is made every day from scratch, and so is their tomato sauce, made only from the best Italian Tomatoes. Brenda's appetizers and fresh salads can be ordered with chicken or steak or as Antipasto. The menu also includes traditional Heros, the entire assortment of Parmigianas: chicken, meatball and eggplant, and a Steak & Cheese with a twist called the Bronx Belly Buster. Brenda's Neapolitan and White pizzas are available with more than 30 toppings. Their beverage menu is includes beer, wine and mineral and sparkling waters.

21311 Garrett Hwy #2, Oakland, MD 21550, Phone: 301-387-1007

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5. Things to Do Near Me: Ace's Run Restaurant & Pub, Oakland, MD

Ace’s Run is a large, cozy contemporary restaurant and pub in Oakland, Maryland, overlooking the lake and offering New American comfort food and drinks at the beautiful semi-circular bar. This family-owned and run spot opened in 2013 and a has a balcony dining area, boat docks, and a menu that changes seasonally. It was one of the first restaurants to offer Farm to Table process. Most of the items on the menu are grown or raised locally including vegetables, meats, cheeses and more. All desserts are made in-house, including fresh ice cream and milkshakes. Open Kitchen Nights feature events such as Pasta Mania – the guests watch their pasta being cooked just the way they like it. The Pub, with panoramic lake views, warm fireplace, and imaginative cocktails, is the popular place to meet friends for a drink with friends.

20160 Garrett Hwy, Oakland, MD 21550, Phone: 301-387-6688

6. Things to Do in Oakland, Maryland: Garrett County Museum of Transportation

Learn all about the different modes of transportation in this unique museum. Home to various exhibits spread throughout two floors, the Garret County Museum of Transportation displays original and well-preserved transportation vehicles dating back to the 1950’s. On the first floor, visitors can learn all about early forms of transportation including sleighs, carriages, and buggies. Engine-powered automobiles are also touched on in the first-floor exhibits along with fire department artifacts. Some of their key displays include an original Garrett County sailboat and snowmobile. Visitors can then view the Deep Creek Gallery on the second floor, which chronicles and displays the history of Deep Creek Lake alongside other Maryland State Parks.

108 E Liberty Street, Oakland, Maryland 21550; Phone: 301-334-3226

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7. Things to Do in Oakland, Maryland: The Alley

Gather at The Alley for some quality time the whole family will enjoy. The bowling alley is great for all skill levels—even young kids—as it features ramps, automatic bumpers, light weight balls, and bowling shoes that go all the way down to a toddler’s size 7. On top of their kid-friendly bowling alley, visitors will also find pool tables, ping pong tables, an air hockey table, a shuffle board table, and an arcade filled with 20 redemption games. Dining isn’t a problem either, thanks for their restaurant which serves up delicious meals and sweet treats alongside both alcoholic and non-alcoholic beverages.

499 Oakland Drive, Oakland, Maryland 21550; Phone: 301-334-3040