Middletown (Connecticut) Restaurants
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Osa
Price: Moderate•Contemporary American•4.8(750)Kevin Wirtes and Rich Garcia of Krust (Middletown), team up in the creation of their latest venture, Osa. Located at 500 Main Street in Middletown, Osa features local food, with a fresh take on New American. The full bar offers crafted cocktails, whiskey, a large wine pour list, and craft beer.Harrie’s Jailhouse - Middletown
Price: Moderate•American•4.7(19)Comfort Cuisine & Classic Cocktails located in the historic 1850s Pameacha Jailhouse. Please note that reservations are only accepted for our upstairs dining room & cell room. Our basement bar is walk ins only.
Outdoor dining in Connecticut
See what locals rave about in Middletown (Connecticut)
- JJakeGreater Boston •9 reviews5.0Dined on Apr 27, 2025Excellent experience - service and food! There were two very large parties there at the same time as us, but we still got plenty of attention and prompt service. When we were placing our order and considering a paella, the waitress let us know that it would take a while, which was both appreciated and an indicator that it would be done right. Food highlights - Gambas a la Plancha - shrimp was excellent. Grilled Octopus was super-tender. Cazuela de Mariscos - seafood broth was amazing. Crema Catalana dessert - don't miss it.More infoEl Pulpo & Tapas Bar - MiddletownPrice: Moderate• Tapas / Small Plates• Middletown•4.3
- CChristinaConnecticut •1 review5.0Dined on Apr 26, 2025We really had a nice time here and the food is both casual and creative which can be hard to balance. Staff is friendly and accommodating, We will be back ….they had me at Parmesan pesto fries and Expresso Martini. This place is a gem if you are looking for a casual relaxing meal and a great cocktail.More infoHarrie’s Jailhouse - MiddletownPrice: Moderate• American• Middletown•4.7
- JJohnGreater Boston •5 reviews4.0Dined on Apr 21, 2025Delicious food with portion sizes that were not too big and not too small - just right.More infoStella D'oroPrice: Expensive• Italian• Middletown•4.6
- OTOpenTable DinerNew York City •4 reviews5.0Dined on Mar 20, 2025I love the consistency of the menu at Fiore’s! Excellent meals every time I go!!More infoFiore II - MiddletownPrice: Expensive• Italian• Middletown•4.7
Trending dishes in Middletown (Connecticut)
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Celebrate special occasion at the best restaurants in Middletown (Connecticut). Our customers recommend Red Fox Restaurant, Osa and Stella D'oro
As of May 9, 2025 there are 9 restaurants in Middletown (Connecticut). Filter by “outdoor dining”, “romantic” or “dog friendly”.
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