We have visited here a few times when staying in the area. The atmosphere is local but fun. Staff is always nice and the food is pretty good. Only thing they can up is the calzone. Pay pretty good money but not a lot of filling and the ends are complete dough. In the end cooked perfectly just needs more filling for the cost. read more

The Penalty Box - Big Bad Bruin - Sports Bars Near Me - Damariscotta, Maine

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The food was way beyond we expected. The beer also very good. But the cheesecake is the kick ass. We had to comeback the next day for the cheese cask. read more

Food always as described. Staff friendly. Pub atmosphere. Daily specials. Known for pizza,surprisingly varied n

It's a sports bar with good quality bar food. Plenty of seating for watching games or events. The service was quick & friendly. Seemed to be a local crowd when we were there. Some desserts were homemade & delicious. read more

horrible customer service! The waitress just walked up and asked if I knew what I wanted yet or what. No Hi, No introduction as a server, just straight bullshit. and not only that her face was clearly showing how happy she was to be there! if I had her name I would tell you guys. read more

The menu here is huge and everything we have tried has been delicious. The pizzas are tasty as are the sandwiches and appetizers. The dining room is spacious and the service is very friendly. Don't forget dessert! read more

Their food is really good food, they have really good service and they are very respectful!!!

Bobby Orr pizza was fantastic. Our friend ordered the Olympian Pizza and it was spot on. Server was very friendly and helpful. When we return for our next Maine vacation we will definitely plan a return trip. read more

Love love love the food very satisfied the owner she's older short grey hair with glasses is the sweetest

We've been here plenty of times for the good food even though there is a huge difference in how regulars or the rest of us are treated. Once we were even asked with a sneer, "Where ya from?". (We live 25 miles away.) This was our first time going with a gluten-free person. The ONLY options are salad, chowder (which our relative can't have) or a 10" pizza. She was told that it can't be made into a calzone, only pizza. The pizza was OK but had to be sent back to be sliced again because it couldn't be ripped apart. It was re-sliced on the aluminum pan so returned with metal shards under it. When we got the bill, we were charged for a 14" as well as given a hidden charge for the GF dough. (The menu says it has the GF option but does not have a charge listed.) Each topping is charged differently depending on the size of the pizza. We were charged $25.25 instead of $18.88 which is still expensive for a 10". We brought it to their attention. The owner came over saying that the card had already been run so couldn't be reversed but he agreed to give us the GF dough free because the waitress forgot to tell us about that charge. He handed us $1.15 and said that we were set. He then argued with us about the expense of printing menus, having to offer GF dough, running a business, etc. He finally raised his voice when we mentioned that GF was listed as an option but had no price listed with it, "Well, it doesn't say 'free'!" Our card was charged the full amount. Nothing had been corrected. The owner told us he had "run the math 3 times." We have enjoyed coming here for a few years now and were able to ignore being treated like we are not locals but we will not be back again now. It is not our relative's fault that she needs GF options nor is it our fault that the charges were run incorrectly. We did not appreciate the owner raising his voice to us. read more

The pizzas here are awesome. I alternate between the Bruin and Orr (Works or all meat). Get a 16" and keep leftovers for later. Box is just small enough to slip into a full size fridge. Gluten free crust available at 14" size. The service is friendly and familiar. Solid staple that is better that delivery or supermarket. Not gourmet like Ottos, but certainly better value for money too. read more

The Penalty Box - 10" Orr - Sports Bars Near Me - Damariscotta, Maine

Stopped here for lunch while on vacation. The menu made everyone happy. Perfect spot for a hungry family!

I ordered the 20 inch pizza with toppings and wings Togo. I walk in an am greeted by the owner. Who ask for my name, and then says your the one with weird pizza. ( if it's that weird then don't offer the toppings ) onion, steak, spinach and artichoke. Been here plenty of times and ordered the same pizza and every other time I've only seen smiling faces and thanks you's, not tonight though. Maybe I caught her on a bad day. I'm not a local, but I can tell you I'll spend my $54 closer to where I live in stead of coming here. Only thing I find weird, is the way you run your business. read more

Usually this place is great, super friendly staff, good food. But tonight we seemed to have annoyed the staff just by showing up. We aren't regulars. All the regulars seemed to be able to order dinner and drinks without attitude. She served one table 3 rounds of drinks before she finally took our order. Server got mad when we asked for a refill of coke said "her shift was over" but she's standing next to us rolling silverware so not sure how we're suppose to know that. They seemed very nice to everyone but us. I ordered a drink and the bartender asked at least 5 other people if that wanted "another" and made them all drinks. Finally my husband politely asked is I could get my drink. Eventually she made it and slammed it down on the corner of the table. Maybe we just look like jerks. Maybe asking for gluten free options pissed then off. Next time I'll get my food to go or just sit in the dining room ( not the pub area with the regulars) where I clearly belong. I hope they have a better night. Food was good but hard to enjoy when it comes with a heaping slice of attitude. read more

Kids love the garlic knots, mozzarella sticks and pizza. This is our go to stop when we are looking for a thicker crust.

The staff is knowledgeable and friendly, and the food is consistently good. We have enjoyed several apps, including the mozzarella sticks, chicken wings, breadsticks, bchicken quesedilla, and others. The pizzas, nachos, subs, burgers, sandwiches, and pastas are always great. Very rarely have we had anything less than delicious. Highly recommend. read more

We ordered two different kinds of pizzas, chicken tenders/fries, burger/onion rings. Food was amazing. Our waitress had a great sense of humor and was awesome. Will definitely be back when we stop through the area again. read more

We recently had two very different experiences here. The first one we stopped in for a drink and to watch some of the Patriots game. The bartender mad a nice margarita and social distancing was comfortable. Several nights later we went back for a drink and the place was packed!!! There was 1 empty table that we were heading to when the bartender (not the same one!) told us we had to sign in first. No problem, was about to sign in when the bartender was clearly heard saying "this is turning into the worst night!" As it was only 6:30 pm and the night was young we took as a clear sign to turn around and walk out. One more thing, I'm not sure that EVERYONE was eying us when we walked in but it was clear that only regulars are welcome! read more

We love all the different types of Pizza here-- although I most frequently order the gluten free Bobby Orr pizza! The staff are kind and to-go orders are typically handled promptly. The only negative is the over full parking lot which can make pick up difficult! Maybe they need to start a curbside pick up! read more

Very very yummy. So much food I couldn't finish.... Will be eating it for dinner tonight.

I'm from New Hampshire so I liked it just fine- the company I was with (from California and New York) we're unimpressed. New Englanders do their pizza differently. Not necessarily for the better- but hey it's nostalgic for me. read more

Very good food, friendly service. When I'm back in my home town of damariscotta I will definitely eat here again. They have everything from sandwiches, burgers, pizza, salads ect. read more

My husband and I and two of our good friends who were visiting from out of town went to dinner and Karaoke at the Penalty Box last night .We arrived at 5:00pm and sat in the bar to have dinner so that we could enjoy the Karaoke entertainment afterward. My husband and our two friends had several cocktails each throughout the evening and I had ONE glass of wine with dinner and DID NOT drink any more alcohol as I chose to be the designated driver At around 8:30 pm my husband and our friends decided to have one more drink before we settled our bill for the evening. The bartenders refused to serve my husband and our friends another drink and when he simply asked Why? She replied " we have a responsibility " OK here is what I do know. We were there for 3 1/2 hours we ALL had a full dinner and my husband and our friends had 3 cocktails each over that 3 1/2 hour period, I had ONE glass of wine with dinner and NOTHING else the rest of the evening as I was the designated driver and both bartenders were fully aware of that! And most importantly is the fact that we were just four senior citizens quietly having dinner and a few drinks. we were NEVER rude or loud or disrespectful or obnoxious or out of control in any way at any time. So I have to ask ? What exactly is the bartender responsible for? When my husband posed this same question to the owner he was told that the conversation was over and he was told to leave immediately or the police would be called! I was in the food and bar business for over fourty years and this horrible experience is a perfect example of what happens when you give someone with zero integrity or common sense a little bit of authority! read more

I have visited the Penalty Box on several occasions and have always had a good meal and a good experience until tonight. in my lifetime I have been to thousands of restaurants and I have never once been charged for a glass of water. this was ordinary water, not bottled water or special water. I was not told that there would be a charge for it when I asked the waitress for a water. When the bill came, I was charged $2.29 for a glass of water. my granddaughter had a soda that was the same price. I really thought a mistake had been made on the bill. Needless to say, I will never go back there and I will tell everyone I know about how this restaurant is gouging it's customers. I was also charged .99 for 2 raw onion rings on a sub. read more

I ordered pizza and wings to go and everything was delicious. It was incredibly busy. I can see why.

We ordered the Celtic pizza for take out. The crust was thick and chewey. The box was saturated with oil. The cheese was rubbery and pesto was tasteless. Would not order again. read more

Good sports bar atmosphere, it was great fun. You can also pick up things to go. The pizza quality is good. Most of the pasta dishes are OK. The burgers are pretty good too. read more

Just finished a wonderful dinner at the Penalty Box. The Heater pizza thin crust was delicious. Samantha our server was wonderful We will be back. read more

Been here a few times. Pizza and calzones appear to be their specialty. Other meals are mediocre. If you're in a hurry, best to order take-out. In restaurant service tends to be slow. Bar area is ok, nothing special, although there is entertainment in the evening. read more

I loved the Penalty Box. I had a calzone and some mozzarella sticks. Both were great. Mozzarella sticks were very normal, nothing special, but still very good. The Calzone was also very good, lots of cheese. My favorite thing about this restaurant was the staff all seemed like they hated each other. You could sense the tension. It was quite entertaining. Little glares here and there, it was funny. Who had happened? Who's fault was it? I'll never know. read more

Great atmosphere, good food and nice beer selection.

Awesome food. Friendly service. thin crust pizza was loved by all. Fried hock basket was amazing!

Just got done eating here. Very busy tonight so it took a while to get the server to come over, but when we ordered the pizza came really quick. The 20" is HUGE and we had half a pizza to take home (2 people dining) so this is a great value. This by far is the best pizza anywhere near here and seriously $28 before tip to dine in two people with a huge pizza and free refill soda?? Home run!! We TOTALLY will be back!! I'm very very picky about my pizza and all I can say is damn. read more

very good food, affordable prices, a nice place for a good family dinner, workers very nice and always helpful with recommended food, i've never had a bad meal there always cooked to perfection. would definitely recommend for families and is a very nice atmosphere for when games are on read more