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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 since 2007. 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 two dining areas and a bar to choose from, you’ll love our warm, inviting ambience. We can ensure the highest quality of food and service. During holidays and weather events, please check our Facebook/ Instagram to check our hours. Thank you.
Quaint, comfy spot offering gourmet sandwiches, American mains & a full bar in a historic space.
Address and Contact Information
Address: 14 W Main St, Middletown, MD 21769
Phone: (301) 371-4433
Website: https://www.themaincup.com/
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The Main Cup
See our latest menu, find our hours, and order online directly from us. Locations in Middletown, MD.
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The Main Cup 14A W Main St. 14 West Main Street, Middletown, MD. Delivery.
The Main Cup | Middletown MD – Facebook
The Main Cup, Middletown. 12031 likes · 57 talking about this · 21718 were here. All American restaurant located in Downtown Historic Middletown, MD.
Reviews
Kenzie Kramer
We stopped by The Main Cup for the second time—our first visit was just for drinks, but this time we stayed for both food and beverages, so it felt right to share a full review.
Parking is a bit tight, located behind the restaurant in a small lot with roughly a dozen spaces. Keep that in mind if you’re visiting during a busy time.
The staff were quick to greet us and get us seated. Everyone we interacted with was friendly, knowledgeable, and attentive throughout our meal.
We started with the buffalo wings. While they don’t offer an all-flats option, the 50/50 mix was fine. The wings were char-grilled with the sauce served on the side, which gave them a great texture—big, juicy, and flavorful.
For dinner, I ordered the blackened chicken tacos and paired them with one of their signature house crushes. We also ordered a side of mac & cheese for our daughter. My husband chose The Maryland Burger (topped with imperial crab) and a fall margarita, along with a crush to compare. He preferred the margarita, noting it was more flavorful and stronger, while the crush tasted mostly like orange juice. Unfortunately, he found the burger rather bland and mentioned it tasted different from what he remembered under the previous ownership—perhaps the recipe has changed. That’s largely why we settled on four stars instead of five.
Our server was pleasant, though we did have to ask several times for water refills and extra napkins—after wings, one paper napkin just isn’t enough.
Overall, the food was decent, and we’d definitely return for a casual lunch. However, nothing particularly stood out to make us eager to come back for dinner.
A few small improvements could easily make the experience great.
… moreParking is a bit tight, located behind the restaurant in a small lot with roughly a dozen spaces. Keep that in mind if you’re visiting during a busy time.
The staff were quick to greet us and get us seated. Everyone we interacted with was friendly, knowledgeable, and attentive throughout our meal.
We started with the buffalo wings. While they don’t offer an all-flats option, the 50/50 mix was fine. The wings were char-grilled with the sauce served on the side, which gave them a great texture—big, juicy, and flavorful.
For dinner, I ordered the blackened chicken tacos and paired them with one of their signature house crushes. We also ordered a side of mac & cheese for our daughter. My husband chose The Maryland Burger (topped with imperial crab) and a fall margarita, along with a crush to compare. He preferred the margarita, noting it was more flavorful and stronger, while the crush tasted mostly like orange juice. Unfortunately, he found the burger rather bland and mentioned it tasted different from what he remembered under the previous ownership—perhaps the recipe has changed. That’s largely why we settled on four stars instead of five.
Our server was pleasant, though we did have to ask several times for water refills and extra napkins—after wings, one paper napkin just isn’t enough.
Overall, the food was decent, and we’d definitely return for a casual lunch. However, nothing particularly stood out to make us eager to come back for dinner.
A few small improvements could easily make the experience great.
Alex Pierce
Great experience here on a Monday for lunch. It was very quiet as we came during the week. The restaurant is clean and beautifully decorated. Our server was fantastic. I ordered the grilled chicken sandwich and my friend ordered the friend chicken sandwich. Bother were delicious and portion sizes were plenty. I will say I felt some of the prices were a little high, but otherwise I enjoyed my experience!
… moreVeronica Cannon
Excellent food and service! Such a surprise to find this gem of a restaurant in Middletown, MD. This place is worth the trip north. Excellent braised short ribs and the best burgers!
… moreAri Kon
Stopped by with my wife, we had some cocktails and a delicious meze platter fir starters. Our main meal was the mains burger with bacon . The burger was great but way to much on all the sauces, a light coating wouldve been sufficient, i prefer to enjoy the meat not fir it to be drowned in all the sauces. Stopped by again with my wife, this time we had potato skin appetizer which was delicious, and the bacon burger. I didn’t get sauce on it this time but we also didnt get medium burgers, they were well done, no pink, tasty but overcooked. Our server Theresa was on point, also the drinks for happy hour cant be beat
… moreKyleOfTheBeard
The Main Cup is a nice American-style restaurant nestled in the heart of Main Street Middletown, MD.
I went around 7:30pm on a Tuesday night. Got seated quickly and my waitress (absolutely wonderful and delightful to talk to) got my drink and starters in. I got a Diet Coke and some wings—the Diet Coke came out in a mason jar, which is a pet peeve of mine that I really dislike (Who likes ribbed glass up against their teeth when they drink??) but, thankfully, it came with a straw.
The wings were BIG with a ton of meat on the bone and very nice buffalo sauce that wasn’t overly intense or spicy.
My entree was Cajun Raviolinis that came with marinated grilled chicken, peas, bell peppers, onions, Parmesan raviolinis, Cajun spiced Alfredo sauce. It was very good but EXTREMELY salty.
My waitress convinced me to go with the brownie sundae for dessert and she was spot on. It was delicious and not too filling!
Overall, The Main Cup is a solid establishment with a ton of great menu options and an excellent staff! It can get a bit pricey and the interior is a bit dark and dim, but the food and great service more than make up for that.
Go try their brunch menu!
… moreI went around 7:30pm on a Tuesday night. Got seated quickly and my waitress (absolutely wonderful and delightful to talk to) got my drink and starters in. I got a Diet Coke and some wings—the Diet Coke came out in a mason jar, which is a pet peeve of mine that I really dislike (Who likes ribbed glass up against their teeth when they drink??) but, thankfully, it came with a straw.
The wings were BIG with a ton of meat on the bone and very nice buffalo sauce that wasn’t overly intense or spicy.
My entree was Cajun Raviolinis that came with marinated grilled chicken, peas, bell peppers, onions, Parmesan raviolinis, Cajun spiced Alfredo sauce. It was very good but EXTREMELY salty.
My waitress convinced me to go with the brownie sundae for dessert and she was spot on. It was delicious and not too filling!
Overall, The Main Cup is a solid establishment with a ton of great menu options and an excellent staff! It can get a bit pricey and the interior is a bit dark and dim, but the food and great service more than make up for that.
Go try their brunch menu!
Gloria Maser
We arrived at our favorite restaurant, expecting good food and great servers. We were not disappointed with servers and greeters, efficient, friendly and accommodating as usual. However, my chicken quesadilla, which is what I normally order, came out with the cheese dried up, as tho it had been under a heat lamp for some time. I shared that with our waitress, who took it to the chef and manager, Ricky. He said he made it and it was fresh. The waitress asked if I wanted to talk with Ricky, I said I did, but he would not talk to me. So, what has always been an enjoyable event, turned into something unpleasant. We have been coming to the Cup at least twice a week for the past 2 years. I’m afraid we will be patronizing Fratellis in the future. It would have been so easy to make this right. Gloria Maser
… moreLouisa Alexander
Cozy atmosphere; restaurant with nice bar, but bar doesn’t impose on dining. Excellent service from start to finish. Everyone in our party thoroughly enjoyed the food (burger, risotto, salad, desserts). I had a salad meal, and I am not exaggerating when I say that it was one of the freshest, most delicious salads I’ve ever had locally. Every ingredient in the salad, from lettuce to avocado and tomato, was perfectly fresh (in February). The chicken was tasty, not over-seaspmed and not dry. As a dinner salad person, I was SUPER pleased. Last but not least is the brown butter cake. Magical! I have to say magical. And the creme brulee had a perfect crust of caramel on top, with a smooth custard beneath. This place is a hidden gem, for sure.
… moreF Scott
The food is so good! We have never had a bad meal here. I highly recommend the Farmers Ravioli. The Veggie & Shroom Risotto is amazing! I added Salmon to mine and it was perfect.
… moreSusan Palmer
Love this place this time of year. Their Holiday drinks menu has so many choices so festive and full of flavor. I had the Holiday mule and it was just the best with the ginger beer and floating cranberries in a frosty copper mule cup. My friend tried different beers and she loved them as well, she also had the sliders which were moist and the perfect light meal. I had the crab dip, full of crab and cheese served with crunchy pita triangles. Our waitress in the bar area was absolutely fabulous, wish I got her name. Just a perfect place to sit and talk and enjoy!
… moreAnnie
We stopped here in Middletown to grab a bite to eat and it was amazing. The interior is gorgeous and the food is great. I highly recommend the mezze platter, especially if you’re going with friends or family. I will definitely be coming here again. Thank you so much!
… more