Best Fun Restaurants in Middletown

11 restaurants available nearby

A photo of Harrie’s Jailhouse - Middletown restaurant

1. Harrie’s Jailhouse - Middletown

new

4.9

Exceptional(5)

Price: Moderate

• American • Middletown

Booked 10 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.

2. Osa

4.8

Exceptional(725)

Price: Moderate

• Contemporary American • Middletown

Booked 20 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 Sally's Apizza - Wethersfield restaurant

3. Sally's Apizza - Wethersfield

4.2

Awesome(156)

Price: Moderate

• Italian • Wethersfield

Booked 64 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.

4. 1741 Pub & Grill

4.3

Awesome(260)

Price: Moderate

• American • Middlefield

Booked 12 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 The Flying Monkey Grill and Bar restaurant

5. The Flying Monkey Grill and Bar

4.6

Exceptional(39)

Price: Expensive

• American • Newington

Booked 20 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

3.1

Good(778)

Price: Expensive

• Contemporary American • Middlefield

Booked 24 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 The Saybrook Fish House restaurant

7. The Saybrook Fish House

4.8

Exceptional(430)

Price: Expensive

• Seafood • Glastonbury

Booked 24 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.

8. Krust

4.8

Exceptional(186)

Price: Moderate

• Pizzeria • Middletown

Booked 14 times today

Wood Fired Pizza - Craft Beer/Cocktails - Whiskey Bar

A photo of Casa Mia On The Green restaurant

9. Casa Mia On The Green

4.2

Awesome(144)

Price: Moderate

• Italian • Rocky Hill

Booked 2 times today

Named as one of the best Italian restaurants in the country by a leading trade association, Casa Mia On The Green in Rocky Hill, CT has been family owned and operated since 1985. Diners enjoy a low-key and welcoming setting in which to engage in the "art of dining".Menu options at Casa Mia On The Green range from a la carte lunch and dinner menus, to a family style menu and a buffet menu. There are multiple catering menus and special holiday options too. Standard choices include appetizers, salads, pasta and risotto specials and an array of seafood and meat dishes. A nice range of vegetarian dishes are also available, and these go beyond pasta with meatless sauces, including meals such as grilled eggplant with gorgonzola, salad and pasta. Ideal for a meal with family or friends, Casa Mia On The Green is a must try restaurant.

A photo of Casa Mia at the Hawthorne restaurant

10. Casa Mia at the Hawthorne

4.3

Awesome(159)

Price: Moderate

• Steakhouse • Berlin

Booked 1 time today

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

B
Brandy
Baltimore / Maryland •10 reviews
5.0
Dined 4 days ago
We had a wonderful brunch at Harries! I’ve been wanting. To try it for awhile and they didn’t disappoint! Fiona was a great server and the food was sooo good! Can’t wait to come back!
More info
Harrie’s Jailhouse - MiddletownPrice: Moderate• American• Middletown
•
4.9
M
Michael
Caribbean •1 review
5.0
Dined 4 days ago
Chefs Andre and Josh presented a wonderful "Christmas Around the World" menu. From the duck tamales to the prime rib, everything was perfectly prepared. Our servers, Makenzie and Ben, kept the food and drinks coming to our large family party. This was a memorable night.
More info
OsaPrice: Moderate• Contemporary American• Middletown
•
4.8
C
carol
New York City •4 reviews
5.0
Dined 5 days ago
Excellent meals for all three of us, prompt service, waiter was attentive, and atmosphere was fun - everyone seemed to be having great time.
More info
Sally's Apizza - WethersfieldPrice: Moderate• Italian• Wethersfield
•
4.2
T
Tory
New York City •2 reviews
5.0
Dined on Dec 20, 2024
Fun night out with friends. Seated quickly, service was good, as was the food. Martinis were great!
More info
The Flying Monkey Grill and BarPrice: Expensive• American• Newington
•
4.6
J
justin
Greater Boston •1 review
5.0
Dined on Dec 13, 2024
Live music was a really pleasant surprise. Nice duo of standup bass and guitar, hi quality americana music. Vegan Chili and Roasted brussel sprouts were both delicious.
More info
1741 Pub & GrillPrice: Moderate• American• Middlefield
•
4.3

Explore OpenTable

Middletown

Best Fun Restaurants in Middletown

Price

Cuisine

Regions

Neighborhoods

Top Rated

Dining Options

Seating Options

Accessibility

11 restaurants available nearby

1. Harrie’s Jailhouse - Middletown

2. Osa

3. Sally's Apizza - Wethersfield

4. 1741 Pub & Grill

5. The Flying Monkey Grill and Bar

6. Fire at the Ridge

7. The Saybrook Fish House

8. Krust

9. Casa Mia On The Green

10. Casa Mia at the Hawthorne

See what locals rave about

Explore OpenTable