The 20 Best Restaurants in Oakland, Maryland

Dutch's at Silver Tree offers a classic steak and seafood experience in a well-kept, lodge-style setting accented by fireplaces. The kitchen focuses on carefully prepared dishes such as crab cakes, scallops, and surf-and-turf combinations, complemented by fresh salads. Attentive, professional service and generously portioned entrees contribute to a satisfying dining experience, with desserts like crème brûlée providing a polished finish.

Lakeside Creamery serves house-made ice cream and fresh waffle cones beside the shores of Deep Creek Lake. Guests choose from a wide range of flavors and toppings, enjoyed either indoors or at outdoor tables overlooking the water. Friendly, energetic staff and a casual, family-friendly setting create a lively spot for a cool treat.

Englanders combines a nostalgic antique shop setting with a classic American diner tucked in the back. The kitchen focuses on hearty comfort fare, from traditional breakfast plates like omelets and biscuits with gravy to burgers and thick milkshakes. Freshly made baked items, including popular cinnamon rolls, add to the appeal, while the quick, attentive service supports a lively, old-time café atmosphere.

Brenda's Pizzeria serves classic, New York–influenced pizza with a well-balanced sauce, flavorful cheese blend, and crisp, satisfying crust. Guests note the consistently fresh-tasting pies and reliable quality, even during busy periods. Attentive, professional service and views over Deep Creek Lake contribute to an enjoyable, laid-back dining experience.

Ace's Run Restaurant & Pub offers lakeside dining with a focus on inventive, flavor-driven dishes and thoughtful presentation. Guests highlight the chef’s creativity and attention to texture, with surprising touches in each plate. A popular midweek feature is the interactive pasta night, where custom pasta dishes are prepared to order at a live cooking station, complemented by attentive, personable service.

Arrowhead Market serves as a long-standing neighborhood hub, combining a full grocery selection with a busy deli and hot food counter. Guests find fresh meats, cheeses, produce, and a range of prepared dishes, including roasted chickens and rotating take-out options. Freshly baked items, such as cinnamon rolls and pepperoni rolls, are frequently highlighted for their appealing flavor. The setting offers the convenience of a market with the feel of a casual, local eatery.

3rd Street Diner serves straightforward American comfort food, from hot roast turkey sandwiches with mashed potatoes and gravy to grilled cheese with tomato soup. Guests mention homemade soups and desserts, generous portions, and consistently satisfying breakfasts and lunches. The atmosphere is simple and unpretentious, with quick, attentive service that adds to the welcoming feel.

The Casselman Cafe Bakery offers a casual spot near Deep Creek Lake for fresh, house-made breakfast and lunch. Guests appreciate hearty breakfast sandwiches, BLTs, and flavorful soups such as Maryland crab. The bakery showcases popular treats including cinnamon sticky buns, pies with flaky pastry, and snack mixes. A steady crowd and inviting atmosphere make it a comfortable place to enjoy simple, well-prepared food.

Honi-Honi Bar offers a vibrant, social setting with ample outdoor seating and frequent live entertainment. Guests enjoy casual favorites such as pizza and nachos alongside a broad selection of summer-friendly frozen drinks. Play areas give families with children space to relax, while attentive staff contribute to the upbeat, welcoming atmosphere.

JG's PUB is a laid-back neighborhood spot known for hearty pub fare and a welcoming, unpretentious vibe. Guests highlight the cheesesteaks, wings, onion rings, and meatballs with garlic bread, along with occasional special dinners such as an Oktoberfest menu. Recent updates to the exterior and interior give the space a refreshed yet still comfortable feel.

Housed in a charming 19th-century Victorian inn, Deer Park Inn offers refined country-style cuisine prepared with fresh, carefully chosen ingredients. Breakfast features thoughtfully made dishes such as pancakes, eggs, and house-baked breads with homemade jams, while dinner showcases skillful, wine-friendly cooking. A small dining room with a working fireplace creates an intimate, romantic setting in the heart of Garrett County.

The Vagabond Taproom offers a focused menu of comforting pub-style dishes, from grilled cheese and pulled pork to hearty salads and seasonal vegetables. A rotating selection of craft beers, playful wine offerings, and house sodas complement the food. The intimate space combines an upscale pub feel with distinctive decor, and attentive staff contribute to an easygoing, welcoming experience.