Gather Here. Eat Well. Celebrate Often.

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Welcome to Oscar’s Restaurant, a Cumberland favorite for great food, cold drinks, and a relaxed, family-friendly atmosphere. From Italian-American classics and steaks to seafood, sandwiches, wings, pasta, and daily specials, Oscar’s is the perfect place for lunch, dinner, drinks, catering, and special gatherings.

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Oscar’s Restaurant has been a Cumberland favorite since 1993, serving up great food, cold drinks, and a welcoming atmosphere for families, friends, and groups of all sizes.

Known for Italian-American favorites, steaks, seafood, sandwiches, pasta, wings, and daily specials, Oscar’s is the kind of place where everyone can find something they love. Whether you’re stopping in for lunch, meeting friends to watch the game, enjoying dinner with family, or planning a special event, we’re here to make every visit feel comfortable and memorable.

With a relaxed Georgetown-style atmosphere, full-service bar, seasonal outdoor patio seating, catering options, and private event space, Oscar’s is more than just a restaurant — it’s a place to gather, celebrate, and enjoy good food with good people.

From our family to yours, thank you for making Oscar’s part of the Cumberland community for over 30 years.

Great Food. Good times. Every Day.

  • Red circular icon with fork and knife silhouettes symbolizing food or dining.

    Delicious food.

    Italian classics, hand-cut steaks, fresh seafood, hearty pasta, crispy wings, flavorful sandwiches, tempting appetizers and much more.

  • Red outline of a beer mug with foam, inside a red circle.

    Full- Service Bar

    Enjoy your favorite drinks and handcrafted cocktails, plus a rotating selection of 13 beers on tap.
  • Icon of two adults and a child holding hands, inside a red circle

    Family friendly

    A comfortable place for the whole family to enjoy — Oscar’s Restaurant offers a warm, welcoming atmosphere where every generation feels at home. From classic Italian-American favorites and tender steaks to fresh seafood and crowd-pleasing kids’ options, our menu has something for everyone. Spacious seating, attentive service, and a relaxed pace make us ideal for weekday dinners, weekend gatherings, and special celebrations. Join us for a casual meal, a family night out, or catering for your next event — family-friendly dining made simple and satisfying.
  • Red alarm clock icon with a circular border and two bells on top.

    Catering.

    Oscar’s Restaurant Catering brings the same Italian‑American favorites, signature steaks, and fresh seafood you love to any event in Cumberland and the surrounding area. Whether you’re planning a family gathering, business lunch, wedding, or casual get‑together, our full‑service and drop‑off catering options are designed to fit your needs and budget. Choose from plated dinners, buffet spreads, party platters, and customizable menus featuring pasta classics, hand‑cut steaks, seasonal sides, and crowd‑pleasing desserts. Dependable delivery, professional setup, and attentive service make hosting effortless—so you can focus on your guests while Oscar’s handles the food. Contact us to discuss menu options, dietary accommodations, and tailored packages for groups of all sizes.
  • A circular icon with a party popper emitting stars and confetti, outlined in red.

    Private events

    Our private event spaces accommodate intimate gatherings to larger parties, ideal for birthdays, rehearsal dinners, business luncheons, and family reunions. Customized menus, flexible seating arrangements, and experienced staff ensure a smooth, memorable event tailored to your needs. Ask about full-service catering, beverage packages, and audiovisual support to make your occasion effortless and enjoyable.

Visit Us

1103 E. Oldtown Road
Cumberland, MD 21502

Hours
Monday - Thursday: 11:00 a.m. – 8:00 p.m.
Friday - Saturday: 11:00 a.m. – 9:00 p.m.
Sunday: 11:00 a.m. – 7:00 p.m.

Phone
(301) 724-7827

 

  • "Great locally owned restaurant! Big portions and everything tasted great! I didn't get a pic of my husband's Philly cheesesteak but he got the small and it was still huge! The menu is good and has a lot of variety so it's hard to choose!

    Cirstin R.

    Bloomfield, Pittsburgh, PA

  • "Oscars food is delicious!! I had turkey and my date had steak. Beautiful salads and perfectly cooked food. Our server, Amber was so efficient and kind. She helped choose from the menu for us and despite how busy she was kept checking on us. The cherry limeade from the bar was so refreshing. Very cute place and we will return."

    Erin B.

    San Francisco, CA

  • "I love Oscar's food. I get something different every time and I love it all. They make a mac n cheese flatbread that is to die for. The ranch is great. Service is great and super quick. Restaurant is super clean and it's a great atmosphere. They have outdoor and indoor dining"

    Abigail B.

    Cresaptown, MD

Something for Every Appetite

From comfort food favorites to hearty entrées, Oscar’s menu is filled with options for every craving. Enjoy Italian classics, fresh seafood, steaks, burgers, sandwiches, wings, salads, pasta dishes, flatbreads, and more.

Whether you’re grabbing a quick lunch, sitting down for dinner, or enjoying drinks with friends, Oscar’s makes every visit feel easy and enjoyable.

Close-up of grilled ribs with a smoky, caramelized exterior, placed on a wooden cutting board.
Close-up of food being taken out of a stainless steel chafing dish with tongs. The food appears to be cooked meat, possibly chicken or beef, garnished with herbs.
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