11 Best Bars in Middletown

Chili's Grill & Bar Tex-Mex • $$
33 Crystal Run Crossing, Middletown

Customers` Favorites

Chicken Bacon Ranch Quesadillas
Crispy Chicken Crispers Combos
Chili's Secret Sauce Burger
Chili's House Mar-Go-Rita
Bottomless Chips & Salsa
Grilled Chicken Fajitas
Bottomless Tostada Chips
Alex's Santa Fe Burger
Molten Chocolate Cake
Southwestern Eggrolls

“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!“

4.1 Good114 Reviews
Scotchtown Craft Bar • $$
741 NY-211 E, Middletown

Customers` Favorites

Braised Short Rib over Gnocchi
Selection of Draught Beer
Cuban Sandwich with Fries
Smokehouse Burger
Short Rib Poutine
Buffalo Wings
French Fries
Onion Rings
Pulled Pork
Craft Beer

“This is such a great spot!!“

4.7 Superb71 Reviews
Nelsons Bar Bar • $
44-46 Roberts St, Middletown

“An unusual "dive bar" in a very unusual town?. It's unusual because it's primarily a black dive bar with a white owner?. She's a sweetheart and I love the place. This town Middletown NY is a unique place I love it! Drinks are good..music is good“

4.8 Superb4 Reviews
Players Bar • $
30 Henry St, Middletown

“great people great staff all around great bar.“

4.3 Superb8 Reviews
Highball Tavern Bar • $
42 Ingrassia Rd, Middletown

Customers` Favorites

Bourbon Chicken Wings
Chicken Cordon Bleu
Macaroni Salad
Chicken Club

“Wow! Food and service were great! We'll be back!“

4.3 Superb11 Reviews
Perla Escondida Mexican Restaurant Mexican • $
133 Wickham Ave, Middletown

“la comida riquísima y la atención de los dueños muy buena 100 % recomendable“

4.1 Good4 Reviews
The Switch Inn Gastropubs • $
126 E Main St, Middletown

Customers` Favorites

Chicken Cutlet Sandwich with Fries
Chicken Cutlet Sandwich w Fries
Chicken or Steak Quesadilla
Burger Deluxe with Fries
Corned Beef and Cabbage
Pint of Domestic Beer
Jumbo Buffalo Wings
Breakfast Burrito
Meatloaf Dinner
Grilled Cheese

“My experience was phenomenal. Will go again.“

4.7 Superb100 Reviews
Hook & Reel Cajun Seafood & Bar Seafood • $$
8 Orange Plaza Ln, Middletown

Customers` Favorites

Fried Oyster and Sweet Potato Fries
Crab Leg and Scallop Boil
Almejas En Salsa Picante
Seasoned Garlic Butter
Chicken Tender Basket
The Perfect Storm
Clam Chowder Soup
Mozzarella Sticks
Snow Crab Legs 1
Shrimp and Fries

“Finally got to Hook & Reel!! Great vibe, great food! We sat at the bar and enjoyed Danielle’s company. Rob, was an incredible insight to the short history of this restaurant and is wonderful. We chatted about the history of this type of venue in Middletown and how to survive. He gets it. While chatting, his head was on a swivel, watching his guests and crew. Rob spoke so highly about his crew, you would think they were family. I am so glad I went and enjoyed the family atmosphere. Well done team!!“

4.5 Superb233 Reviews
DeStefano's Olde Erie Pubs • $$
7 W Main St, Middletown

Customers` Favorites

Steamed Clams in Garlic Butter and Roasted Red Pepper Tower
Ravioli Fresca Appetizer Exquisite
Veal Parmagiana with Penne Pasta
Portion of Chicken Parmesan
Chicken Parmesan and Fries
Meatball Parmigiana Hero
Chicken Parm with Penne
Loaf of Italian Bread
Pasta and Meatballs
Bread and Olive Oil

“I had the pleasure of being at Destefano's for a bridal shower this past weekend. The food was amazing, the atmosphere cozy and the staff was so friendly - although it was their day off, they served with bright smiles and were very accommodating. I would definitely recommend them for dinner or catered party. Thank you!“

4.4 Superb89 Reviews
Clemson Bros. Brewery American • $$
22 Cottage St, Middletown

“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!!“

4.4 Superb155 Reviews
Copperbarn Coffeebar & Eatery Coffee & Tea • $$
368 E Main St, Middletown

Customers` Favorites

Italian Eggplant Ciabatta Sandwich
Sesame Crusted Grilled Ahi Tuna
Steak and White Cheddar Panini
Blueberry Ricotta Pancakes 2
Eggplant Parmesan Lasagna
California Club Sandwich
Cinnamon Bun Pancakes
Surf and Turf Burger
Pulled Pork Sliders
Barn blt Sandwich

“Just had lunch at Copper Barn. Had the avocado soup....soooo good!! My husband and I both had a turkey BLT on a panini. Took half of mine home so I could have a piece of their sour cream coffee cake (the best!). With all that said, the icing on the cake was the server, Shanelle. She was informative, personable and sweet with a great sense of humor!!! Thank you Shanelle and Copper Barn for a great lunch!!😊😊“

4.3 Superb126 Reviews

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