Craving small-town charm, mountain views, and outdoor adventure? Head to Oakland, Maryland! Nestled in the Allegheny Mountains, this historic town offers lake escapes, train rides, scenic trails, and cozy downtown vibes. Whether you're into foliage, festivals, or farm-fresh food, Oakland is a western Maryland gem.

Best Time to Visit

The best time to visit Oakland is from late spring through fall (May to October). Enjoy mild weather, fall foliage, and lively festivals. Winter is also great for snow sports and cozy cabin stays near Deep Creek Lake.

How to Get There

  • If you are traveling by car: Oakland is located off U.S. Route 219 in western Maryland, about 3 hours from Washington, D.C., and 2 hours from Morgantown, WV or Pittsburgh, PA.
  • By Bus: Local Garrett Transit provides limited bus service within the county; regional bus options are minimal.
  • By Train: There is no Amtrak service directly to Oakland, but nearby Cumberland (about 1 hour away) has a station served by the Capitol Limited route.

Where to Stay

  • Oakland Motel – Affordable and convenient lodging close to downtown and local attractions.
  • Inn at Deep Creek – Lakeside lodge-style inn with a pool and cozy mountain vibes, just 15 minutes away.
  • Haley Farm Inn and Retreat Center – Rustic-chic retreat with spa services, perfect for couples or wellness getaways.

Top Attractions

Hike to Stunning Waterfalls at Swallow Falls State Park

Hike to Stunning Waterfalls at Swallow Falls State Park

© walt1957/stock.adobe.com

Swallow Falls State Park is located on the west bank of the Youghiogheny River, about nine miles from Oakland, Garrett County, Maryland. This must-see 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, MA 21550, Phone: 301-387-6938

Step Into Railroading History at the Oakland B&O Railroad Museum

Step Into Railroading History at the Oakland B&O Railroad Museum

© The Oakland B&O Railroad Museum

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

Discover Local Heritage at the Garrett County Historical Museum

Discover Local Heritage at the Garrett County Historical Museum

© Garrett County Historical Museum

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.

Garrett County Historical Museum, 107 S 2nd St, Oakland, MD 21550, Phone: 301-334-3226

Where to Eat

Satisfy Your Pizza Craving at Brenda's Pizzeria

Satisfy Your Pizza Craving at Brenda's Pizzeria

© Brenda's Pizzeria

Brenda's Pizzeria 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

Dine Lakeside with a View at Ace's Run Restaurant & Pub

Dine Lakeside with a View at Ace's Run Restaurant & Pub

© Ace's Run Restaurant & Pub

Ace's Run Restaurant & Pub 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

If you are traveling with kids:

Explore Vintage Rides at the Garrett County Museum of Transportation

Explore Vintage Rides at the Garrett County Museum of Transportation

© 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 Garrett 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

Bowl, Game, and Eat at The Alley Family Fun Center

Bowl, Game, and Eat at The Alley Family Fun Center

© 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

Must-see if you are a first-time visitor:

  • Deep Creek Lake State Park – Swim, hike, or boat on Maryland’s largest freshwater lake.
  • Swallow Falls State Park – Explore trails and waterfalls, including the tallest in Maryland.
  • Downtown Oakland – Browse antique shops, art galleries, and cafes in a charming historic district.

If you are interested in local events:

  • Autumn Glory Festival (October) – A five-day celebration of fall with parades, crafts, food, and foliage tours.
  • Little Yough Summer Music Festival – Free concerts in the park every Friday evening (July–August).
  • Oakland Winter Fest (February) – Ice sculptures, sledding, and winter-themed activities downtown.

If you are looking for unique day trips within 30 Minutes of Oakland, Maryland:

  • Deep Creek Lake (10–15 min) – Go boating, fishing, or zip-lining, or relax at lakeside parks and resorts.
  • Wisp Resort (15–20 min) – Ski in winter, golf or ride mountain coasters in summer at this year-round resort.
  • Herrington Manor State Park (20–25 min) – Rent a cabin, paddle on the lake, or hike forested trails.
  • Friendsville (20–25 min) – Raft the Youghiogheny River, visit quirky shops, or relax riverside.
  • Grantsville (25–30 min) – Visit Spruce Forest Artisan Village or walk the historic Casselman Bridge.
  • Accident, MD (15–20 min) – Stop by FireFly Farms Creamery, stroll quaint shops, or try a local brewery.
  • New Germany State Park (25–30 min) – Ski, sled, fish, or hike in this peaceful forest hideaway.

FAQ:

  • Where is Oakland located?
    • Oakland is a small town in the west-central part of Garrett County, near Deep Creek Lake and only a few miles from the source of the Potomac River.
  • What can visitors see in the Oakland Historic District?
    • The Oakland Historic District features a number of beautifully restored Victorian buildings, which today house galleries, a pharmacy, a library, and fashionable boutiques.
  • What is a must-visit natural attraction near Oakland?
    • Swallow Falls State Park is located on the bank of the Youghiogheny River and is home to Muddy Creek Falls, a stunning 53-foot waterfall—the highest falls in Maryland.

At a Glance:


Best Time to Visit Places to Stay Tips for Visiting
Spring (March-May) – Mild temperatures and blooming flowers. The Lodge at Wisp – A comfortable stay near Deep Creek Lake. Explore Swallow Falls State Park – See stunning waterfalls and scenic hiking trails.
Summer (June-August) – Warm weather, ideal for lake activities. LakeStar Lodge – A lakeside retreat with beautiful views. Enjoy boating on Deep Creek Lake – Rent kayaks or take a scenic boat tour.
Fall (September-November) – Crisp air and stunning autumn foliage. Inn at Deep Creek – A cozy and rustic getaway. Take a scenic drive through Garrett County – Experience vibrant fall colors in the mountains.

Map:


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