Dine-In Restaurant
Full-service restaurant with generous portions of comfort food classics. Multiple seating areas including bar and dining room.
- Weekly dinner specials
- Extensive sandwich and sub menu
- Hot and cold appetizers
⭐ 4.4 (704 reviews)
Visibility: 87/100Old Oscar's stands out in Cumberland's dining scene for its massive portions, affordable prices, and authentic local tavern atmosphere featuring a beautiful historic bar. Known for their exceptional subs, homemade hot chips, and famous Reuben sandwich, this restaurant consistently delivers quality comfort food that keeps customers coming back. The friendly staff and multi-purpose venue offering regular dining, bar service, and catering makes it a versatile choice for any occasion.
Based on 704 customer reviews
Address: 1103 E Oldtown Rd, Cumberland, MD 21502, USA
Phone: (301) 724-7827
Hours: Friday 11:00 AM – 9:00 PM, Monday 11:00 AM – 8:00 PM, Sunday 11:00 AM – 7:00 PM, Tuesday 11:00 AM – 8:00 PM, Saturday 11:00 AM – 9:00 PM, Thursday 11:00 AM – 8:00 PM, Wednesday 11:00 AM – 8:00 PM
Parking: Free parking available in front, behind, and beside building
Peak times: Friday-Saturday evenings 6-9pm
Nearby neighborhoods: South Cumberland, Rolling Mill, Decatur Heights
Nearby landmarks: Near I-68 corridor, 5 minutes from downtown Cumberland, Close to Western Maryland Railway Station
Full-service restaurant with generous portions of comfort food classics. Multiple seating areas including bar and dining room.
Historic bar area popular with locals featuring cold beer and casual atmosphere. Keno gaming available for entertainment.
Off-site catering for events and gatherings with the same generous portions and quality food.
Separate dining area available for private parties and special occasions with personalized service.
⭐ 4.4 out of 5
704 total reviews
Consistently high ratings over past year with strong praise for portions and value. 18 new reviews this month.
“Passing through Cumberland and wanted to stop at one of my favorite local joints, only to find they're closed Sundays so we started looking at other options. Came across this place, saw great reviews and decided to give it a try. After one visit, it will absolutely become a regular for us. It's not too far off the highway. Parking can be difficult at their busiest times, but there's space in front, behind and beside the building. They offer catering, private dining, regular dining and bar area. Inside has a beautiful old bar that was filled with locals. There's a keno machine and regular/weekly dinner specials. The beer is CHEAP and cold. The food portions are LARGE and delicious. Prices for food are fair and Staff is friendly and helpful. Zero complaints and can't wait to go back. Absolutely check them out.”
— Ashley Gilles“Everytime we go here the food is tasty. Had the wings, cajun chicken wrap with hot chips and Chicken crab dip sandwich with ranch chips. Do not pass up trying the homemade hot chips. Delicious! The staff is always pleasant. Good experience all the way around.”
— So Blessed“All I can say is WOW ❗. You better bring an appetite.. So many good choices on the menu. Have something for everyone. We all got the " SUBS " steak and cheese, and Italian sub. They were Huge.. Very reasonable prices and had attentive staff. Highly recommend stopping here to eat. We will be back for sure .”
— Colin Gnibus“This restaurant is excellent. The food portions are huge. You will not leave hungry for sure. If your traveling on a budget just order 1 and split it, you will still be satisfied. The steak sub was absolutely huge and delicious. However for all you rueben lovers you won't find a better one anyyyywhere. Our waitress was stellar , great atmosphere. We will be back.”
— Jennifer SchrinerNo, Old Oscar's is closed on Sundays. We're open Monday through Saturday.
Yes, we provide catering services for events and gatherings with our full menu available.
Yes, we have parking spaces in front, behind, and beside the building, though it can be busy during peak times.
Yes, we have a beautiful historic bar area with cold beer at great prices and a keno machine for entertainment.
Our subs, especially the steak and cheese and Italian, are very popular, along with our famous Reuben sandwich and homemade hot chips.
Status: Open now
Peak hours: Friday-Saturday 6-9pm
Daily specials: Weekly dinner features
Popular this month: Reuben sandwich, Steak subs, Wings
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