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Restaurants near Old Middletown Post Office

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378 restaurants available nearby

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A photo of Stella D'oro restaurant
1. Stella D'oro
4.7
Exceptional(117)
$$$$
• Italian • Middletown
Booked 6 times today
Stella D’oro, a family owned restaurant, was established in 1993 in Old Saybrook, Connecticut. Reopened in Middletown, Connecticut serving fine, northern Italian food.At Stella D’oro you’ll enjoy the best Italian cuisine with a full bar and various wines.View our full, up to date menu. We offer salads, pasta, steak, seafood, and more!
A photo of T-Bone Prime Steakhouse restaurant
2. T-Bone Prime Steakhouse
3.9
Excellent(53)
$$$$
• Steak • Middletown
Booked 5 times today
Located on Main Street in Middletown, CT, T-Bone Prime Steakhouse offers prime cuts of beef, exquisite wine pairings, and a welcoming atmosphere. Join us for elevated cuisine and delicious cocktails. We can’t wait to serve you! To keep up to date with our latest events, announcements, and more, make sure to follow us on social media.
A photo of Fiore II - Middletown restaurant
3. Fiore II - Middletown
4.7
Exceptional(9)
$$$$
• Italian • Middletown
Booked 4 times today
A Taste of Italy in the Heart of MiddletownLocated in downtown Middletown, Fiore II Restaurant offers inspired Italian dishes in a European-style eatery. A local favorite, Fiore II consistently impresses with quality ingredients, great service and a comfortable atmosphere.
A photo of Mezzo Grille - CT restaurant
4. Mezzo Grille - CT
3.8
Excellent(47)
$$$$
• Gastro Pub • Middletown
Booked 7 times today
Mezzo Grille is where elevated dining meets high-energy entertainment in the heart of Central Connecticut. By day and early evening, it delivers a polished yet approachable experience—crafted cocktails, a refined comfort-driven menu, and a vibrant patio atmosphere that sets the tone for any occasion. Hired in 2026, Mezzo's NEW Culinary Director focuses on taking familiar favorites and elevating them—classic dishes reimagined with higher-quality ingredients, bold flavors, and a modern touch that keeps the menu exciting yet approachable. As the night builds, Mezzo transforms seamlessly into a lively social destination, blending top-tier DJs, live music, and a dynamic crowd into an experience that feels both upscale and electric.Known for its versatility and attention to detail, Mezzo Grille offers something for everyone—whether it’s an intimate dinner, after-work drinks, or a full night out.
A photo of Harrie’s Jailhouse - Middletown restaurant
5. Harrie’s Jailhouse - Middletown
4.9
Exceptional(46)
$$$$
• American • Middletown
Booked 2 times today
Comfort Cuisine & Classic Cocktails located in the historic 1850s Pameacha Jailhouse. Please note that reservations are only accepted for our upstairs dining room & cell room. Our basement bar is walk ins only.
A photo of Osa restaurant
6. Osa
4.8
Exceptional(810)
$$$$
• Contemporary American • Middletown
Booked 17 times today
Kevin Wirtes and Rich Garcia of Krust (Middletown), team up in the creation of their latest venture, Osa. Located at 500 Main Street in Middletown, Osa features local food, with a fresh take on New American. The full bar offers crafted cocktails, whiskey, a large wine pour list, and craft beer.
A photo of Red Fox Restaurant restaurant
7. Red Fox Restaurant
4.5
Awesome(448)
$$$$
• Steakhouse • Middletown
Booked 8 times today
Red Fox is a family owned gourmet restaurant that serves top of the line Mediterranean/American cuisine for a reasonable price. With an extensive wine collection and amazing entrée options we are sure to please. We look forward to serving you! Outside dinning available!!!!
A photo of Campagna restaurant
8. Campagna
4.5
Awesome(14)
$$$$
• Italian • Middletown
Booked 2 times today
Campagna Restaurant is a family run restaurant committed to providing delicious food and great service in a friendly neighborhood atmosphere.
A photo of Red Fox Amore restaurant
9. Red Fox Amore
4.7
Exceptional(81)
$$$$
• Italian • Middlefield
Booked 5 times today
Come join us at the Red Fox Amore Italian Kitchen !
A photo of Tavern At The Armory restaurant
10. Tavern At The Armory
3.5
Very Good(21)
$$$$
• American • Middletown
With appealing nightly specials and a tidy list of drinks, Tavern at the Armory provides a charming culinary experience, serving up traditional New England cuisine in a beautiful space. Helmed by Executive Chef Kyle Bates, Tavern at the Armory provides a nice quaint, neighborhood dining experience. During the warmer months, the restaurant's space expands to include a beautiful courtyard. Open for breakfast, lunch, and dinner daily.

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Dining near Old Middletown Post Office at a glance

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Most popular restaurant

popular restaurant

Harrie’s Jailhouse - Middletown

4.9

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Discover local gems

Exceptional reviews

Most popular cuisine

popular cuisine

Contemporary American

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$30 and under

See what locals rave about

From verified diners like you
From verified diners like you
  • Heather
    New York City •5 reviews
    4.0
    Dined 7 days ago
    Overall it was an excellent meal and experience. It seemed they were understaffed and some staff maybe needed more direction on how to be helpful. Our waitress was working very hard. It took a long time to get some bar drinks. Waters were not kept full.
    More info
    T-Bone Prime Steakhouse$$$$• Steak• Middletown
    •
    3.9
  • Diane
    Connecticut •8 reviews
    5.0
    Dined on May 18, 2026
    We had a nice Quiet dinner with great service, drinks and food from an extensive menu. Delicious bread was served complimentary. Will go back another time for HappyHour at the bar!
    More info
    Stella D'oro$$$$• Italian• Middletown
    •
    4.7
  • ShelbyGold
    Greater Boston •177 reviews
    5.0
    Dined on May 10, 2026
    What a hidden gem! Great tasting food, excellent service, and huge portions. Everyone enjoyed their meals. Everything was unique and fresh. I ordered the house salad. Very fresh and tasty. The salad could serve 4 people! My friend ordered the spring chicken sandwich with onion straws. Stating the sandwich was the best she ever had! My mom and sister ordered the Folsom chicken sandwich with onion straws and fries. Everything was mouth watering they said! Packed with flavor! The strawberry rhubarb pie and carrot cake were so delicious! I don’t even eat that pie annd I enjoyed it. BCP snacks were out of this world! Moe excellent service! Great waiter who was genuine and fun! Thank you!😊
    More info
    Harrie’s Jailhouse - Middletown$$$$• American• Middletown
    •
    4.9
  • Angel
    San Diego •2 reviews
    5.0
    Dined on Apr 25, 2026
    Fiore’s is our go-to restaurant for family celebrations! Their garlic knots are AMAZING as well as their espresso martinis!! Service is absolutely amazing every single time!
    More info
    Fiore II - Middletown$$$$• Italian• Middletown
    •
    4.7
  • PriscillaFGold
    New York City •13 reviews
    5.0
    Dined on May 31, 2019
    Great summer atmosphere on back deck. Food was terrific
    More info
    Mezzo Grille - CT$$$$• Gastro Pub• Middletown
    •
    3.8

Discover best restaurants near Old Middletown Post Office

Discover the charm of the Old Middletown Post Office, a historic landmark that adds character to the neighborhood. Where to Eat Near Old Middletown Post Office? The dining scene near this iconic site is vibrant and eclectic, offering something for every palate. Enjoy hearty American classics in a casual setting, or savor Mediterranean flavors that highlight fresh ingredients. If you're in the mood for something comforting, you can dive into the rich tastes of Italian cuisine accompanied by fine wines. Options range from laid-back bistros serving burgers and steaks to delightful spots for pasta and seasonal dishes. With a variety of atmospheres, dining near the Old Middletown Post Office is sure to be a memorable experience.

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