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Restaurants near Middletown Woodrow Wilson High School

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365 restaurants available nearby

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A photo of Harrie’s Jailhouse - Middletown restaurant
1. Harrie’s Jailhouse - Middletown
4.8
Exceptional(49)
$$$$
• American • Middletown
Booked 7 times today
Comfort Cuisine & Classic Cocktails located in the historic 1850s Pameacha Jailhouse.
A photo of Pastaio | Middletown restaurant
2. Pastaio | Middletown
4.5
Awesome(25)
$$$$
• Italian • Middletown
Booked 17 times today
Pastaio is a Chef Owned restaurant in Middletown, CT specializing in hand made pastas and innovative Italian-American specialties. Our passion is creating a memorable experience for our guests with the highest quality ingredients, expertly prepared with care and delivered with the highest level of hospitality.
A photo of Stella D'oro restaurant
3. Stella D'oro
4.4
Awesome(129)
$$$$
• Italian • Middletown
Booked 5 times today
Stella D’oro, a family owned restaurant, was established in 1993 in Old Saybrook, Connecticut. Reopened in Middletown, Connecticut serving fine, northern Italian food.At Stella D’oro you’ll enjoy the best Italian cuisine with a full bar and various wines.View our full, up to date menu. We offer salads, pasta, steak, seafood, and more!
A photo of Osa restaurant
4. Osa
4.8
Exceptional(833)
$$$$
• Contemporary American • Middletown
Booked 12 times today
Kevin Wirtes and Rich Garcia of Krust (Middletown), team up in the creation of their latest venture, Osa. Located at 500 Main Street in Middletown, Osa features local food, with a fresh take on New American. The full bar offers crafted cocktails, whiskey, a large wine pour list, and craft beer.
A photo of T-Bone Prime Steakhouse restaurant
5. T-Bone Prime Steakhouse
4.1
Excellent(74)
$$$$
• Steak • Middletown
Booked 6 times today
Located on Main Street in Middletown, CT, T-Bone Prime Steakhouse offers prime cuts of beef, exquisite wine pairings, and a welcoming atmosphere. Join us for elevated cuisine and delicious cocktails. We can’t wait to serve you! To keep up to date with our latest events, announcements, and more, make sure to follow us on social media.
A photo of Illiano's Ristorante and Pizzeria restaurant
6. Illiano's Ristorante and Pizzeria
new
(0)
$$$$
• Italian • Middletown
Nestled in the ethnically diverse dining destination of Middletown, Connecticut, Illiano's South Main Street has been a beloved family favorite since its opening in March 2001. Founded by Vinnie Scileppi, this inviting Italian restaurant and pizzeria offers a traditional atmosphere where guests are genuinely treated like family. Illiano's is renowned for its unwavering commitment to fresh, quality ingredients, generous portions, and first-rate service, delivering a delightful fusion of classic Italian favorites with a distinct New York flair. It's a cherished local establishment where culinary excellence consistently meets warm hospitality, ensuring every visit is a memorable and comforting experience for the community.
A photo of Mezzo Grille - CT restaurant
7. Mezzo Grille - CT
3.8
Excellent(50)
$$$$
• Gastro Pub • Middletown
Booked 2 times today
Mezzo Grille is Connecticut’s Social Destination, located in the heart of Downtown Middletown. Combining elevated American cuisine, handcrafted cocktails, live entertainment, and a vibrant atmosphere, Mezzo offers an unforgettable experience for lunch, dinner, happy hour, weekend brunch, and nightlife.Led by Culinary Director Christopher Maxson, the menu features elevated comfort food made with high-quality ingredients, bold flavors, and a modern approach to classic favorites. Guests can enjoy signature dishes, creative cocktails, and a lively indoor-outdoor dining experience.Whether you’re joining us for an intimate dinner, after-work drinks, live music, watch parties, or a night out with friends, Mezzo delivers a unique blend of hospitality and entertainment. Featuring a spacious patio, live bands, DJs, private event spaces, and an energetic social atmosphere, Mezzo Grille is where great food, drinks, sports, and nightlife come together.
A photo of Red Fox Restaurant restaurant
8. Red Fox Restaurant
4.7
Exceptional(467)
$$$$
• Steakhouse • Middletown
Booked 12 times today
Red Fox is a family owned gourmet restaurant that serves top of the line Mediterranean/American cuisine for a reasonable price. With an extensive wine collection and amazing entrée options we are sure to please. We look forward to serving you! Outside dinning available!!!!
A photo of Fiore II - Middletown restaurant
9. Fiore II - Middletown
4.7
Exceptional(13)
$$$$
• Italian • Middletown
Booked 2 times today
A Taste of Italy in the Heart of MiddletownLocated in downtown Middletown, Fiore II Restaurant offers inspired Italian dishes in a European-style eatery. A local favorite, Fiore II consistently impresses with quality ingredients, great service and a comfortable atmosphere.
A photo of Campagna restaurant
10. Campagna
4.5
Awesome(16)
$$$$
• Italian • Middletown
Booked 3 times today
Campagna Restaurant is a family run restaurant committed to providing delicious food and great service in a friendly neighborhood atmosphere.

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Dining near Middletown Woodrow Wilson High School at a glance

Updated on

Most popular restaurant

popular restaurant

Krust

4.8

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Discover local gems

Exceptional reviews

Most popular cuisine

popular cuisine

Contemporary American

Average check amount

$30 and under

See what locals rave about

From verified diners like you
From verified diners like you
  • Sherry
    New York City •4 reviews
    5.0
    Dined 7 days ago
    Food was delicious service was great. Sit in bar area more private than dinning room
    More info
    Stella D'oro$$$$• Italian• Middletown
    •
    4.4
  • Laura
    1 review
    5.0
    Dined 7 days ago
    Consistently fabulous drinks and food! Creative and flavorful!!!
    More info
    Osa$$$$• Contemporary American• Middletown
    •
    4.8
  • shanna
    New York City •3 reviews
    4.0
    Dined 7 days ago
    Great ambience, nice server. Presentation of food was great. However ordered steak medium well and it was beyond well. However, I would eat here again
    More info
    T-Bone Prime Steakhouse$$$$• Steak• Middletown
    •
    4.1
  • Ruth
    Connecticut •1 review
    5.0
    Dined on Oct 24, 2026
    This place is great !. Wonderful ambience. Excellent food. Real value
    More info
    Harrie’s Jailhouse - Middletown$$$$• American• Middletown
    •
    4.8
  • Jovonnie
    1 review
    5.0
    Dined on Oct 21, 2026
    A Wonderful Surprise and an Exceptional Dining Experience! Since Pastaio had only opened a couple of months ago, I wasn’t quite sure what to expect, but my partner and I were absolutely delighted with our experience! From the moment we arrived, everything was fabulous. The drinks were excellent, our waiter was attentive and welcoming, and the ambiance was beautiful and inviting. I ordered the scallops with mushroom risotto, which was delicious, while my partner had the veal ossobuco with cheesy polenta, and it was fantastic! Every dish was full of flavor and beautifully prepared. For such a new restaurant, Pastaio is off to an incredible start! We had a wonderful evening and truly enjoyed every aspect of our dinner. We will definitely be back and highly recommend giving this restaurant a try. A fantastic addition to the dining scene!
    More info
    Pastaio | Middletown$$$$• Italian• Middletown
    •
    4.5

Discover best restaurants near Middletown Woodrow Wilson High School

Discover the rich history and vibrant atmosphere surrounding Middletown Woodrow Wilson High School, a key institution in the community’s educational landscape. Where to Eat Near Middletown Woodrow Wilson High School? Near the high school, you’ll find an eclectic array of dining options perfect for students, families, and visiting guests. Enjoy a lively dining scene that includes casual taverns with classic American fare, cozy pizzerias serving wood-fired pies, and charming steakhouses offering savory dishes with a Mediterranean twist. Each spot promises a welcoming ambiance that's ideal for unwinding after school or elevating any special occasion. Explore an appealing blend of flavors and cuisines that reflect the community’s diverse tastes while enjoying convenient access to delightful meals just a short stroll away.

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