8 Best American Restaurants in Middletown

“Recently we reviewed service from a young man Monty.Monty was polite, courteous n made us comfortable by meeting our needs.Monty is an asset to Chills. Go Monty!“

“We had our wedding here on 10/4/25 and it was absolutely incredible! The venue itself was gorgeous and had such a great charm to it. All of our guests couldn’t stop complimenting us on how great it really was. Our photographer kept saying how good a place to take photos it was. Obviously we had high expectations for this night and it was exceeded. My wife said that it was so much better than she had ever dreamt it could be. The staff went above and beyond and made our special day as stress free as can be. Elaina and Steven were fantastic! Everyone was, but unfortunately I only wrote down those two names so apologies to anyone else who may have been working this event but THANK YOU to everyone. Friendly and patient staff I can’t recommend this place enough. The food was incredible and the beers were cold. They accommodated us so well and we are extremely thankful. If you’re looking for a place to host an event this is it! Or if you’re just looking to grab a drink and a bite this is also the place to go. Thank you to everyone at Clemson for making this the best night of our lives!!“

“Been coming here for years. Actually love this diner by far. Today was the worst. I previously put in my review about today’s visit to the Americana so I won’t put it in again. I just want to clarify that I would always give this place 5 stars except for today. Had a sloppy and somewhat ride waitress that didn’t even get the whole order right and it wasn’t much that we ordered. Had to also be someone different or stingy cooking today because my BLT had more tomatoes and lettuce than it did bacon. Seriously??? TODAY I GICE A 2 STAR , and never want that sloppy somewhat rude waitress again.“

“We have eaten here many times and love it so much! The ingredients are super fresh, the flavors and combinations are expertly put together, and the owner is a true showman who clearly loves the food and sharing it with the community. The danish dog is my favorite, and my husband loves the Italian sausage with onions. Even the basic chili dog is better than average, and his inventive sauces add so much flavor to the dogs that they can’t be replicated anywhere else. The building is small and it’s crowded and dingy and sometimes smoky inside, but we truly feel that it adds to the charm and makes the experience even more unique. Just go - you’ll be so glad you did!“

“My experience was phenomenal. Will go again.“

“This is such a great spot!!“

“A welcome addition to Hudson Valley NY menu changes just enough to keep it interesting and the food is always prepared and presented correctly wait staff are congenial and helpful if needed interesting and eye appealing inside with plenty of room for all diners“

“Harrison was awesome! I recommend the lemon drop martini he makes the best! great wings, wonderful atmosphere, awesome service with a smile 🌟 🌟 🌟 🌟 🌟“