The Main Cup
Crab Cake
Wine & Cake

Welcome to The Main Cup


The Main Cup is an All-American restaurant that sits on the National Historic Road in Middletown, Maryland. Our locally owned and operated restaurant has been in business for 10 years. In that time, we have developed a large number of regular customers who love our wonderful environment, delicious food, and unbeatable service. The quality of our food is excellent.

Everything is made FRESH, and with four dining areas to choose from, you’ll love our warm, inviting ambience. The owners are very involved and hands on, so they can ensure the highest quality of food and service. Have questions? Contact us today.



Upcoming Events and Holiday Hours





  The Valley Jazz Jam – The second Thursday of every month 7:30pm to 10:00pm


Come in and check out our new Happy Hour Menu! (we have some great bar food!!)


NEW HOURS! Happy Hour Monday-Friday 3pm-6pm


After Dinner Happy Hour at the Bar: Friday and Saturdays 9pm-11pm




Our History

The Main Cup is located in Historic Downtown Middletown, Maryland. Its name is derived from the building’s history, which began more than 100 years ago, when C.F. Main began making and selling ice cream here.

Main’s Ice Cream and Butcher Shop became a renowned Maryland institution as the business grew regionally. Presidents and state officials were known to stop at Main’s on their way to Shangri-La, now known as Camp David.

Ice cream was last churned here in 1969, and the Main family subsequently sold the factory.

Main's Ice Cream


Main Cup Construction Map

As of January 2017, Middletown, Maryland has begun the long anticipated Streetscape Project with the State Highway Administration. Our beautiful town will be updated with new sidewalks, new pavement and gutters, landscaping down the entire Main Street (Route 40A) and a new water main. This is projected to be a two-year project.

In order to get to the historic downtown and The Main Cup during construction hours of 9am to 3pm, there are alternative roads that will bring you to your destination with fewer delays.

From Frederick: Traveling on Rt. 40A, make a left onto Middletown Parkway at the light. Turn right at the stop sign onto Holter Rd. At the end of Holter at the stop sign, make a right onto Rt. 17. Make your second left onto Washington Street and park either in our lot on your right or go down two blocks to the Elm Street lot also on your right.

From Boonsboro: Traveling on Rt. 40A, make a left onto North Pointe Terrace. At stop sign make a left onto West Green Street. Parking is located in the Municipal Lot behind Town Hall or you can go down to Rt 17, make a right and pass over Main Street, then turn right onto Washington Street and then another right into our lot.



One feature that sets us apart from other restaurants is our large number of dining areas, which creates a truly fantastic atmosphere for people to dine out. The full-service restaurant and bar are open from 11 am to closing time. Our friendly staff is always on hand to help you with anything you need.

14 W Main St Middletown, MD 21769


Bar Hours

Mon - Thurs 11am to 10pm Friday 11am to Midnight Saturday 8am to Midnight Sunday 9am to 9pm

Grill Hours

Mon - Thurs 11am to 9pm
Friday 11am to 10pm
Saturday 8am to 10pm
Sunday 9am to 8pm

Featured on BuzzFeedWe Accept Visa, MasterCard, Discover, AmEx, Cash & Check