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Best Date Night Restaurants in Middletown, Connecticut

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195 restaurants available nearby

How are Featured results ranked

A photo of Stella D'oro restaurant
1. Stella D'oro
4.8
Exceptional(121)
$$$$
• Italian • Middletown
Booked 2 times today
Stella D’oro, a family owned restaurant, was established in 1993 in Old Saybrook, Connecticut. Reopened in Middletown, Connecticut serving fine, northern Italian food.At Stella D’oro you’ll enjoy the best Italian cuisine with a full bar and various wines.View our full, up to date menu. We offer salads, pasta, steak, seafood, and more!
A photo of T-Bone Prime Steakhouse restaurant
2. T-Bone Prime Steakhouse
4.5
Awesome(60)
$$$$
• Steak • Middletown
Booked 2 times today
Located on Main Street in Middletown, CT, T-Bone Prime Steakhouse offers prime cuts of beef, exquisite wine pairings, and a welcoming atmosphere. Join us for elevated cuisine and delicious cocktails. We can’t wait to serve you! To keep up to date with our latest events, announcements, and more, make sure to follow us on social media.
A photo of Osa restaurant
3. Osa
4.8
Exceptional(816)
$$$$
• Contemporary American • Middletown
Booked 4 times today
Kevin Wirtes and Rich Garcia of Krust (Middletown), team up in the creation of their latest venture, Osa. Located at 500 Main Street in Middletown, Osa features local food, with a fresh take on New American. The full bar offers crafted cocktails, whiskey, a large wine pour list, and craft beer.
A photo of River: A Waterfront Restaurant & Bar restaurant
4. River: A Waterfront Restaurant & Bar
4.3
Awesome(3303)
$$$$
• Steakhouse • Wethersfield
Booked 28 times today
At River: A Waterfront Restaurant & Bar, a multi-tiered deck will allow those who wish to dine alfresco a spectacular, panoramic view of the river and the Putnam Bridge. The views are equally sensational from the interior space where every table in the dining room and every seat in the bar enjoy the magnificence of the setting.River: A Waterfront Restaurant & Bar features Prime Steaks and fabulously prepared Italian food, including house-made fresh pasta, wood-fired artisanal pizzas, locally-sourced seafood, and beautifully handcrafted desserts.
A photo of Ruth's Chris Steak House - Hartford restaurant
5. Ruth's Chris Steak House - Hartford
4.8
Exceptional(1951)
$$$$
• Steakhouse • Hartford
Booked 22 times today
Ruth's Chris Steak House serves the finest aged, corn-fed USDA Prime beef. Broiled in a trademark 1800 degree oven & served on a plate heated to 500 degrees, your steak is presented sizzling hot at your table. In addition to steak, the menu features an assortment of chops, as well as fresh seafood and lobsters. We serve only the finest produce and offer over seven different types of potatoes. Dinner is not complete without trying one of our homemade desserts. Ruth's Chris is also proud of its award winning wine list featuring over 225 domestic and imported selections. At Ruth's Chris Steak House, there is truly something for everyone!
A photo of Red Fox Restaurant restaurant
6. Red Fox Restaurant
4.4
Awesome(451)
$$$$
• Steakhouse • Middletown
Booked 6 times today
Red Fox is a family owned gourmet restaurant that serves top of the line Mediterranean/American cuisine for a reasonable price. With an extensive wine collection and amazing entrée options we are sure to please. We look forward to serving you! Outside dinning available!!!!
A photo of Fleming's Steakhouse - West Hartford restaurant
7. Fleming's Steakhouse - West Hartford
4.8
Exceptional(1700)
$$$$
• Steakhouse • Hartford
Booked 33 times today
Your West Hartford Fleming's is located in the historic Educational Building, just off West Hartford Center and next to the Noah Webster Library. Fleming's in West Hartford is an outstanding choice to enjoy an exceptional Prime steak, glass of wine or handcrafted cocktail. Whether you're celebrating a special occasion, hosting a business dinner or simply wanting to enjoy a night out - we will create a safe and memorable evening in our Dining Room. If you prefer to enjoy your fine dining experience at home, you can order and pay for lunch or dinner online and then pick up curbside or select from one of our delivery partners.
A photo of Harrie’s Jailhouse - Middletown restaurant
8. Harrie’s Jailhouse - Middletown
4.8
Exceptional(46)
$$$$
• American • Middletown
Booked 1 time today
Comfort Cuisine & Classic Cocktails located in the historic 1850s Pameacha Jailhouse. Please note that we currently only accept reservations for groups of 6 or more. We have PLENTY of walk in seating options for 6 or less : we look forward to seeing you soon !
A photo of Market Place Kitchen & Bar | Newington restaurant
9. Market Place Kitchen & Bar | Newington
4.6
Exceptional(190)
$$$$
• American • Newington
Booked 20 times today
Market Place, known for its American tavern style cuisine! We celebrate and encourage local, organic and sustainably harvested food and spirits. Open seven days a week, outdoor dining, and brunch Saturdays and Sundays. We look forward to you trying our inventive, seasonally inspired cuisine and cocktails. Eat sustainably, live well, and enjoy your experience at Market Place!
A photo of Mezzo Grille - CT restaurant
10. Mezzo Grille - CT
new
3.8
Excellent(49)
$$$$
• Gastro Pub • Middletown
Booked 1 time today
Mezzo Grille is Connecticut’s Social Destination, located in the heart of Downtown Middletown. Combining elevated American cuisine, handcrafted cocktails, live entertainment, and a vibrant atmosphere, Mezzo offers an unforgettable experience for lunch, dinner, happy hour, weekend brunch, and nightlife.Led by Culinary Director Christopher Maxson, the menu features elevated comfort food made with high-quality ingredients, bold flavors, and a modern approach to classic favorites. Guests can enjoy signature dishes, creative cocktails, and a lively indoor-outdoor dining experience.Whether you’re joining us for an intimate dinner, after-work drinks, live music, watch parties, or a night out with friends, Mezzo delivers a unique blend of hospitality and entertainment. Featuring a spacious patio, live bands, DJs, private event spaces, and an energetic social atmosphere, Mezzo Grille is where great food, drinks, sports, and nightlife come together.

See what locals rave about

From verified diners like you
From verified diners like you
  • AdamGold
    Atlanta •34 reviews
    5.0
    Dined 6 days ago
    Excellent service and the pork chops were terrific
    More info
    Ruth's Chris Steak House - Hartford$$$$• Steakhouse• Hartford
    •
    4.8
  • Sonny
    Hawaii •8 reviews
    5.0
    Dined 7 days ago
    Love the food here, always one of my favorite meals!
    More info
    Osa$$$$• Contemporary American• Middletown
    •
    4.8
  • Kathy
    Caribbean •1 review
    5.0
    Dined on Jun 20, 2026
    We always enjoy our time at Red Fox. The food is great.
    More info
    Red Fox Restaurant$$$$• Steakhouse• Middletown
    •
    4.4
  • TJ
    Greater Boston •2 reviews
    5.0
    Dined on Jun 18, 2026
    Came to Mezzo with a group of friends to watch a World Cup game and had a great experience. The atmosphere was awesome, the crowd was into the match, and there wasn’t a bad seat in the house. The food really impressed me. I got the Steak Frites and it was cooked perfectly. The burgers at our table looked incredible too, even though I didn’t get a chance to try one. It’s exactly the kind of elevated bar food you hope to find but rarely do. Great service, great drinks, and a perfect spot to watch a big game. We’ll definitely be back!!
    More info
    Mezzo Grille - CT$$$$• Gastro Pub• Middletown
    •
    3.8
  • ShelbyGold
    Greater Boston •182 reviews
    5.0
    Dined on May 10, 2026
    What a hidden gem! Great tasting food, excellent service, and huge portions. Everyone enjoyed their meals. Everything was unique and fresh. I ordered the house salad. Very fresh and tasty. The salad could serve 4 people! My friend ordered the spring chicken sandwich with onion straws. Stating the sandwich was the best she ever had! My mom and sister ordered the Folsom chicken sandwich with onion straws and fries. Everything was mouth watering they said! Packed with flavor! The strawberry rhubarb pie and carrot cake were so delicious! I don’t even eat that pie annd I enjoyed it. BCP snacks were out of this world! Moe excellent service! Great waiter who was genuine and fun! Thank you!😊
    More info
    Harrie’s Jailhouse - Middletown$$$$• American• Middletown
    •
    4.8

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