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Oakland is a quick drive along US Route 219, southwest of Deep Creek Lake.
- 1 Oakland B&O Railroad Museum, 117 E Liberty St, ☏ . 10:00AM-3:00PM Fri and Sat; 12:00PM-3:00PM Sun (also 10:00AM-3:00PM Wed and Thu in Summer).
- 2 Garrett County Museum of Transportation, 107 S 2nd St, ☏ . 10:00AM - 3:00PM Fri and Sat.
- 3 Our Town Theater, 121 E Center St, ☏ . Theatrical plays and performances.
- 4 Garrett County Historical Museum, 107 South Second St, ☏ , ✉ email@example.com. 10AM - 3PM Mon-Sun (Summer); 10AM - 3PM Thu-Sat (Winter). Garrett County exhibits include the county's founding, its history, and the way of life for its historical residents.
- 1 Herrington Manor State Park, 222 Herrington Lane (From Oakland, take Liberty Street westbound, continue onto Herrington Manor Road, turn left into the park entrance), ☏ . Herrington Manor State Park is a 365-acre (1.5-sq km) forest. There are hiking paths, a swimming beach, and a fishing pier. Boats, canoes, and kayaks are available to rent from mid-April to mid- October.
- 1 Book Mark'et and Antique Mezzanine, 111 S 2nd St, ☏ . 9:30AM - 5:30PM Mon-Fri; 9:30AM - 5:30PM Sat; Closed Sun. Bookstore. Large collection of books for children.
- 2 Englanders, 205 E Alder St, ☏ . 8:30AM - 3PM, Mon-Sun. Antique store with a restaurant in the back.
- 3 Alders Antiques and Gifts, 200 E Alder St. 10AM - 5PM Mon-Fri; 9AM - 5PM Sat-Sun. Antique store.
- 4 Cabin Fever Antiques and Collectibles, 17 E Liberty St, ☏ . 10AM - 5PM Fri-Sun. Antique store.
- 1 [dead link] The Cornish Manor, 830 Memorial Dr, ☏ . M-Sa 11AM-9PM, Su 11AM-8PM. A great deal for a rather fancy American restaurant, located in a pretty, historic mansion. $20-35.
- 2 Cornish Cafe, 106 S 2nd St, ☏ . 8AM - 4PM Mon-Sat. Coffee, espresso, baked goods, light lunch.
- 1 Oakland Motel, 243 North 3rd St, ☏ . A newly renovated, clean, fine motel, which is going to be the best dirt cheap option in the Deep Creek Lake area. $50-60.
- Cabins at Herrington Manor State Park, 222 Herrington Lane (From Oakland, take Liberty Street westbound, continue onto Herrington Manor Road, turn left into the park entrance), toll-free: . Rent a rural cabins surrounded by a state park. Cabins have electricity, heat, beds, bathrooms with a shower, kitchens with refrigerator and dishes, and wood-burning fireplaces. Guests must bring their own towels, bed sheets, pillows, pillow cases, blankets, soap, and food. Cabins sleep two, four, or six people, depending on size. Two cabins are accessible for people with physical disabilities.