Oakland Travel Guide

Plan your next trip to Oakland, Maryland with this comprehensive travel guide including attractions, activities, local culture, safety tips, transportation options, and more.


Introduction to Oakland

Oakland is a small town located in Garrett County in Western Maryland, in the United States of America. Surrounded by mountains, lakes, rivers, and forests, Oakland offers a unique blend of outdoor adventures and cultural experiences. Whether you’re into history, nature, or food, Oakland has something for everyone. This comprehensive tour guide will help you plan your next trip to Oakland, Maryland.

List of Places to Visit in Oakland

Culturally Important Attractions: Museums and Historical Places

  • The Garrett County Historical Society Museum showcases the history of the area, including exhibits on the logging and railroading industries that once thrived here.
  • The Oakland B&O Railroad Museum is a restored train station that pays tribute to the important role the railroad played in the town’s development.

Natural Attractions of Oakland: Outdoor Adventures and Scenic Views

  • Deep Creek Lake State Park offers a variety of activities, including hiking, camping, fishing, and boating on the lake.
  • Swallow Falls State Park features a stunning waterfall, hiking trails, and opportunities for swimming and fishing.
  • The Savage River State Forest is the largest forest in Maryland and offers hiking trails, camping, and hunting.

Hiking/Biking Routes of Oakland

  • The Mountain-Maryland Trails are a network of scenic trails that stretch for over 50 miles through the mountains surrounding Oakland. They offer opportunities for hiking, biking, and horseback riding.

Best Things to Do in Oakland: Activities and Tours

  • Take a scenic drive along the National Road, which runs through Oakland and features historic sites and beautiful views.
  • Go on a guided tour of the Oakland Historic District to learn about the town’s rich history and architecture.
  • Attend the Oakland Autumn Glory Festival, a 5-day celebration of fall with parades, live music, and food.

Week-Long Itinerary for Oakland

Day Activity
1 Explore the Garrett County Historical Society Museum and the Oakland B&O Railroad Museum
2 Hike the trails at Swallow Falls State Park
3 Spend the day on Deep Creek Lake, renting a boat or paddleboard
4 Drive the National Road and stop at historic sites along the way
5 Take a guided tour of the Oakland Historic District
6 Go camping or hiking in the Savage River State Forest
7 Attend the Oakland Autumn Glory Festival

Food and Drink Scene of Oakland

Must-Try Dishes

  • Maryland crab cakes are a popular local dish. Try them at a seafood restaurant like Dutch’s at Silver Tree.
  • The Cornish Pastie is another local specialty. It’s a meat-filled pastry that’s perfect for a quick lunch.
  • For a sweet treat, try a slice of the “mile high” apple pie at Cornish Cafe.

Local Beverages

  • The Mountain State Brewing Company offers a variety of craft beers and seasonal brews made with local ingredients.
  • Try a glass of wine from the Deep Creek Cellars, a local winery that specializes in dry, European-style wines.

Where to Stay in Oakland: Hotels, Hostels, and Guesthouses

  • The Lake Pointe Inn is a luxurious bed and breakfast overlooking Deep Creek Lake.
  • The Suites at Silver Tree offers spacious suites with lakefront views and a range of amenities.
  • For a more budget-friendly option, try the Oakland Motel, which offers clean rooms at a reasonable price.

What to Buy in Oakland: Souvenirs and Local Products to Bring Home

  • Visit the Oakland Farmers Market for fresh produce and handmade crafts from local artisans.
  • The Swallow Falls Inn Gift Shop sells souvenirs and gifts featuring the park’s waterfall.
  • Shop for antiques and collectibles at Savage River Antiques and Unique Finds.

Local Culture and Customs of Oakland

  • Oakland has a rich history, and its residents take pride in preserving the town’s heritage and traditions.
  • The Autumn Glory Festival is a significant event in the town, with the entire community coming together to celebrate the changing of the seasons.

Best Time to Visit Oakland

  • The fall is a particularly beautiful time to visit Oakland, with the changing leaves and the Autumn Glory Festival.
  • Summer is also a popular time, with outdoor activities like boating, fishing, and hiking.

Do’s and Don’ts of Oakland

Do:

  • Take advantage of the outdoor opportunities, including hiking, boating, and fishing.
  • Support local businesses and artisans by shopping at local farmers markets and gift shops.

Don’t:

  • Don’t litter or damage the natural environment.
  • Don’t ignore the town’s rich history and cultural heritage.

Safety and Health

Safety in Oakland

  • Oakland is a safe town, but visitors should still take necessary precautions, such as locking cars and valuables.
  • Visitors should be aware of wildlife in the nearby forests, including bears and snakes.

Health in Oakland

  • Visitors should be careful when hiking or engaging in other outdoor activities to avoid injury.
  • There are several medical facilities in and around Oakland, including Garrett Regional Medical Center.

Getting to Oakland: Transportation Options and Logistics

Airports Near Oakland

  • The nearest major airports are Pittsburgh International Airport (PIT) and Baltimore/Washington International Thurgood Marshall Airport (BWI).

Bus Stations Near Oakland

  • The closest bus station is in Cumberland, Maryland, about 20 miles away from Oakland.

Other Options

  • Visitors can also drive to Oakland, with easy access from the National Road (Route 40) and Interstate 68.

How to Get Around in Oakland

  • Most attractions in Oakland are within walking distance of each other, but visitors may want to rent a car or bike to explore the surrounding mountains and forests.

Where to Go Next from Oakland: Nearby Destinations and Excursions

  • Cumberland, Maryland, is a historic city with a charming downtown and beautiful architecture.
  • The nearby Nemacolin Woodlands Resort offers luxury accommodations, golf courses, and a casino.

Conclusion

Oakland, Maryland, is a hidden gem in Western Maryland, offering a unique blend of outdoor adventures, cultural experiences, and small-town charm. Whether you’re into hiking, history, or food, Oakland has something to offer. Plan your next trip to Oakland using this comprehensive tour guide and get ready for an unforgettable experience.