Best Cozy Restaurants in Middletown

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodFusion / EclecticComfort Food

Regions

HartfordMiddlesex

Neighborhoods

BerlinGlastonburyMiddlefieldMiddletownNewingtonWethersfield

Top Rated

Good for business mealsGood for groupsGood for special occasionsGreat for brunchGreat for happy hourGreat for live music

Dining Options

All dining options

Delivery only

Takeout only

Seating Options

BarCounterStandardHigh TopOutdoor

Accessibility

Wheelchair access

10 restaurants available nearby

How are Featured results ranked

1. Stella D'oro

4.5

Awesome(88)

$$$$Price: Expensive

• 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 Harrie’s Jailhouse - Middletown restaurant

2. Harrie’s Jailhouse - Middletown

4.5

Awesome(20)

$$$$Price: Moderate

• American • Middletown

Booked 1 time 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.

3. Campagna

4.3

Awesome(10)

$$$$Price: Expensive

• Italian • Middletown

Booked 1 time today

Campagna Restaurant is a family run restaurant committed to providing delicious food and great service in a friendly neighborhood atmosphere.

A photo of Tavern At The Armory restaurant

4. Tavern At The Armory

3.7

Very Good(14)

$$$$Price: Moderate

• American • Middletown

Booked 1 time today

With appealing nightly specials and a tidy list of drinks, Tavern at the Armory provides a charming culinary experience. This neighborhood restaurant serves up traditional New England cuisine in a beautiful space. Helmed by Executive Chef Kyle Bates, the seasonal menu offers classic delights like braised short ribs, clam chowder, herb-encrusted salmon, and Angus beef burgers. Tavern at the Armory provides a nice backdrop for social luncheons – enjoy a meal next to the fireplace while savoring a cool beer. During the warmer months, the restaurant's space expands to include a beautiful courtyard. Tavern at the Armory is open for breakfast, lunch (starting April 1), and dinner daily.

A photo of The Flying Monkey Grill and Bar restaurant

5. The Flying Monkey Grill and Bar

4.4

Awesome(106)

$$$$Price: Expensive

• American • Newington

Booked 12 times today

The Flying Monkey- a local business offering authentic fusion cuisine, in an inviting atmosphere Featuring acclaimed Jazz and Blues artists to enhance your dining experienceLet Your Monkey Fly!Established 2016.

6. Fire at the Ridge

3.8

Excellent(807)

$$$$Price: Expensive

• Contemporary American • Middlefield

Booked 2 times today

All year-round casual mountain side dinning in the spectacular grounds of Powder Ridge Mountain Park & Resort.Inspired by native New England flavors and locally-sourced ingredients, Fire at the Ridge is an unexpected gem in Middlefield, CT offering indoor, terrace or firepit dinning, locally brewed beers, and craft cocktails. Saturday night outdoor live musicSunday brunch & outdoor Summer markets. Check the event calendar at https://fireattheridge.com/ for weekly Live music and outdoor events.

A photo of Sally's Apizza - Wethersfield restaurant

7. Sally's Apizza - Wethersfield

4.4

Awesome(225)

$$$$Price: Moderate

• Italian • Wethersfield

Booked 32 times today

Sally's Apizza is a popular pizzeria located in Wethersfield, Connecticut. It is the fifth location of the famous Sally's Apizza restaurant in New Haven, Connecticut. Sally's Apizza is known for its thin-crust pizza, which is cooked in a coal-fired oven and topped with fresh, high-quality ingredients. Sally's Apizza Wethersfield also offers a variety of Italian classics, including fried mozzarella, chicken parmesan, salads, calamari, and Calabrian chicken wings. The restaurant has a casual, family-friendly and lively atmosphere that is a favorite among locals and visitors alike.

A photo of The Saybrook Fish House restaurant

8. The Saybrook Fish House

4.7

Exceptional(477)

$$$$Price: Expensive

• Seafood • Glastonbury

Booked 9 times today

Saybrook Fish House is the spot to go to in the area when craving seafood and great wine. The venue uses quality ingredients that really make their dishes standout. The seafood used comes from the New England coast. Saybrook Fish House is open for business seven days a week. It's a great eatery for celebrations and for fun date nights.From the raw bar, diners can dig into jumbo shrimp cocktail and oysters on the half shell. For appetizers, the restaurant offers everything from fried mozzarella and mussels in white wine, to baked mushrooms and crab cakes. Clam lovers must try the fried whole belly clam entrée, which is fried to perfection. Another seafood favorite is the king crab legs served with decadent drawn butter.

9. 1741 Pub & Grill

4.5

Awesome(278)

$$$$Price: Moderate

• American • Middlefield

Booked 3 times today

While our signature burgers are the stars, we offer a wide array of sandwiches and entrees that will surely please. A fully stocked bar with signature cocktails and great local draft beer on tap compliment our great food.

A photo of Casa Mia at the Hawthorne restaurant

10. Casa Mia at the Hawthorne

4.2

Awesome(165)

$$$$Price: Moderate

• Steakhouse • Berlin

Casa Mia at the Hawthorne is one of the premier destinations in Connecticut for banquets, fine dining, and entertainment. Our large facility is located on the Berlin Turnpike right in the heart of the state. In between New Haven and Hartford, we’ve hosted area business, families, and tourists. Call for reservations or stop in for nightly entertainment.Lounge & EntertainmentIf fantastic time is in your game plan then huddle up to Lounge 2421 at the Hawthorne. It’s the ultimate arena. Catch the big game, tackle your appetite with our fabulous bar and lounge menu and favorite beverage while enjoying live entertainment.Special OccasionsWhether you are planning a shower, baptism, communion, birthday celebration or any other affair, we will provide the proper menus and address any special needs that will make your event a special one!

See what locals rave about

From verified diners like you

J
Joseph
Greater Boston •18 reviews
5.0
Dined 6 days ago
Love this place. Great brunch. Delicious bloody Mary’s.
More info
The Flying Monkey Grill and BarPrice: Expensive• American• Newington
•
4.4
L
Lynn
Greater Boston •8 reviews
5.0
Dined on Jun 12, 2025
What a fun atmosphere, beautiful old building! Food and drinks were excellent and service was top notch
More info
Stella D'oroPrice: Expensive• Italian• Middletown
•
4.5
A
Andrea
Greater Boston •1 review
5.0
Dined on May 18, 2025
The value for the delicious food was incredible. I told everyone I spoke to the next day about my rave reviews. I will definitely be returning to that restaurant.
More info
CampagnaPrice: Expensive• Italian• Middletown
•
4.3
J
Jenny
Seattle / Eastern Washington •2 reviews
5.0
Dined on May 11, 2025
This place has the best atmosphere. We ate in their outside dining area which was really fun. Food was great too. Service was excellent.
More info
Harrie’s Jailhouse - MiddletownPrice: Moderate• American• Middletown
•
4.5
P
Patricia
Connecticut •1 review
5.0
Dined on Apr 20, 2025
Everyone was very helpful, dining area had very nice decor for Easter The food was very good and quite plentiful! Totally enjoyable
More info
Tavern At The ArmoryPrice: Moderate• American• Middletown
•
3.7

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