OSA - Middletown
About This Spot
Stepping into OSA in Middletown feels like entering a space where thoughtful care shapes every detail. The warm, inviting interior blends understated charm with just enough polish to mark it as a place for intentional, unrushed dining. Whether it’s a quiet weekday evening or a lively Friday night, the rhythm here encourages guests to settle in, savoring moments between shared plates and gentle conversation.
The atmosphere builds quietly around a carefully curated menu that honors both familiar comfort and inventive twists. Snacks arrive with an artful simplicity—fresh vegetables, wood-roasted oysters, and intriguingly textured tofu—each bite crafted to coax out layers of natural flavor. Moving through the mains, dishes bring together bold and subtle notes, from spiced lamb preparations to the nuanced embrace of house-fired seafood, inviting diners to explore tastes that feel both rooted and unexpected.
OSA’s wine selection quietly complements the culinary experience, offering a range that can elevate an evening from casual to celebratory without ever feeling ostentatious. Sparkling, rose, and white wines bring balance and brightness, encouraging small discoveries throughout a meal.
This is a place where the staff’s genuine attentiveness makes an impression—not only with their knowledge but with the simple kindness that makes each visit feel personal and well-considered. It’s a spot where the care taken in the kitchen is matched by the ease found at the table, creating moments that linger beyond the meal.
What’s Available Here
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Outdoor seating
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Takeaway
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Dine-in
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Delivery
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Fast service
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Great beer selection
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Great cocktails
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Great dessert
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Great wine list
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Serves local specialty
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Dinner
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Solo dining
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Wheelchair-accessible car park
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Wheelchair-accessible entrance
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Wheelchair-accessible seating
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Wheelchair-accessible toilet
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Alcohol
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Beer
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Cocktails
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Coffee
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Comfort food
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Food
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Food at bar
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Small plates
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Spirits
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Vegetarian options
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Wine
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Dinner
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Dessert
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Seating
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Table service
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Bar on site
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Toilet
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Wi-Fi
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Wi-Fi
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Casual
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Cosy
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Trendy
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Upmarket
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Family friendly
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Groups
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Tourists
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Dinner reservations recommended
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Accepts reservations
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Credit cards
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Debit cards
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NFC mobile payments
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Credit cards
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High chairs
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Free of charge street parking
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Paid parking lot
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Paid street parking
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Parking
Location & Hours
| Monday | Closed | |
| Tuesday | 05:00 PM - 09:00 PM | |
|---|---|---|
| Wednesday | 05:00 PM - 09:00 PM | |
| Thursday | 05:00 PM - 09:00 PM | |
| Friday | 05:00 PM - 10:00 PM | |
| Saturday | 05:00 PM - 10:00 PM | |
| Sunday | 05:00 PM - 09:00 PM |
Sally A. 04 Jan 2026
Osa is a gem located in Middletown Connecticut. With its stunning interior and friendly weight staff, this is definitely a place to check out. We've been two times now and the service and food quality are consistent. The first time we went I had a fish dish and I didn't care for it. It was a little too smoky and fishy for me. But it looks lovely. What I remember from our first visit was the burger that my husband had so when we recently revisited I knew that was the thing to get. And I have no regrets. Everything was delicious Including the cocktails. While there are so many places to visit in Middletown and we have lots to explore, we definitely recommend making Osa a priority.
Eric Dowling 19 Dec 2025
A fantastic experience from start to end. It was super easy to get a reservation on a Friday night and when we got there our server was incredibly knowledgeable and helped us pick the perfect dishes. Starting with the corn ribs and the octopus are a strong recommendation from me. I ordered the chicken Milliese and my friend got a burger. Both were perfect. The side salad helped with the chickens heaviness. But ending the night with the caramel bread pudding is the best and really only choice. The atmosphere makes you feel like you aren't in Middletown, CT it's chic and fun and also very easy to have a conversation at. One of the top spots I have been to in Connecticut
Todd Fellerman 17 Dec 2025
LOVE this gem in Middletown! Such an adorable ambiance and look inside. They had a great food and drink menu. Everything we had was very good (pear salad, various dips, breads, oysters, wines). Definitely will come back here, as I want to try more things!
Chris Connelly 15 Dec 2025
The level of detail this place puts into each dish is notable. The chefs go the extra mile in terms of flavor, and I like how it’s a smaller place, ideally leaving the kitchen to more time and care for each dish. A little expensive, but seemingly worth every penny. A great place to celebrate a special occasion, but pricey enough to keep to a once in a while treat. Amazing overall, couldn’t recommend enough.
Melissa Oddo 05 Dec 2025
I have eaten at OSA many times and always LOVE the experience there. When we ate there this past weekend, it prompted me to take a moment to finally write them a well-deserved 5 star review. On this night, I was on the fence about ordering the corn ribs to start and asked our server Vanessa about them. Though they sounded tasty, my husband and I decided not to get them. Vanessa was so kind and actually brought us some anyway so that we could see exactly what she was talking about. They were SO GOOD! Not only was this gesture beyond sweet, she continued to provide us exceptional service throughout the night- checking in just enough but also giving us space to enjoy our first date-night out in a while. The food, drinks, and service are always a win at OSA.
Shalin Shah 03 Dec 2025
OSA was fantastic. Super cool vibe, very reasonably priced for the quality and great staff. I sat at the bar and had the bread, octopus, pasta and dessert. Everything was gorgeous, well balanced and nicely proportioned. Jay was my bartender and server at the bar and HE WAS AMAZING. I was in the mood for a fun drink and he invented one for me. Great spot - it will be my first choice if I’m ever back in Middletown.
Michael Astorino 24 Oct 2025
Osa is a world class restaurant that happens to reside in Middletown, CT. The food is excellent and constantly updated by the season. BEN is the best. We’ve been coming here for several years and he makes us feel at home here, take care of us and goes above and beyond every time. And the atmosphere, somehow every time we’re at OSA, conversations flow better, jokes are funnier, the restaurant just brings out the best in people. Raving review, but it is a special place.