Diners' Choice: Great for outdoor dining restaurants in Middlesex

OpenTable

Updated June 05, 2025

Looking for the best restaurants that are great for outdoor dining in Middlesex? You’re in the right place. Each month, OpenTable analyzes nearly 2 million global diner reviews from the past four months. We sort the results by location and category to help you discover new favorite restaurants. It's a great partnership: you reserve, eat, and review. We listen...and deliver the results for all to benefit. Enjoy!

The Essex

4.9

4.9 (1069)

$31 to $50

American

Old Saybrook

About the restaurant

Set in the heart of downtown, across from the Katharine Hepburn Cultural Arts Center, the “new” Essex will continue to offer the progressive, modern, approachable cuisine that has made it a top restaurant in the region. Whether it’s a pre-theater dinner, a casual gathering with friends, or a tasting menu for a special evening, guests can gather at The Essex to create memories with family and friends while enjoying excellent cuisine.

The Essex menu showcases modern American cuisine that draws inspiration from the land, sea and deep heritage of the Connecticut River Valley, using the freshest locally sourced products available from farm and sea. All will inspire an ever-changing menu of progressive interpretations of timeless dishes.

"Voted Best New Restaurant in New England" Yankee Magazine
"Best Restaurants in Connecticut" CT Magazine
"Not to be Missed" Town & Country Magazine
"Rising Chef Star" CT Mag

Top review

TamiVIP

Dined 4 days ago

I had 2 amazing birthday dinners here - the tasting menu is always a feast! Great service, good ambiance and a gorgeous interior make it a good choice for any occasion

Luigi's Restaurant - Old Saybrook

4.9

4.9 (116)

$30 and under

Italian

Old Saybrook

About the restaurant

Coming Soon!

Top review

RussellVIP

Dined 4 days ago

Service was great they were friendly, attentive and professional. The food was excellent. Had the steak it was cooked to the right temperature , juicy and tasty. The drinks were great. What more can we ask from a restaurant.

Little Pub- Old Saybrook

4.8

4.8 (149)

$30 and under

American

Old Saybrook

About the restaurant

Great food, generous drinks, and a lively pub atmosphere you'll feel right at home in. A rustic neighborhood gathering place with a relentless focus on customer service, value, and fun.

Top review

Tammy

Dined on May 29, 2025

Our server, Kyle, was great. Friendly and attentive. Food was amazing and came out quick. The restaurant was full on our side but not noisy. My parents were in town for my 50th and it was a perfect place to have a casual yummy dinner.

Fresh Salt

4.5

4.5 (1582)

$31 to $50

Seafood

Old Saybrook

About the restaurant

Fresh Salt is more than just a restaurant; it is a place to enjoy one another’s company and experience the breathtaking views of the Long Island Sound quietly intertwined with the Connecticut River. Utilizing the chef’s simple yet high quality approach, the fresh, seasonal local ingredients of Connecticut are transformed into beautifully inspired dishes. Our Local Food Commitment allows us to work with local farmers and artisans to ensure the quality of locally grown ingredients from the sea, land and soil. These fresh ingredients and vibrant tastes of Fresh Salt are available daily for breakfast, lunch and dinner. Located right on the water means seriously fresh seafood and our menu definitely delivers. From the beloved Lobster Roll to the cherished Clam Chowder and so many more specialties, Fresh Salt dishes are guaranteed to please every palate. We offer indoor and outdoor dining, outdoor dining is based on a first come first serve basis, outdoor dining is non-reservable.

Top review

lisaVIP

Dined 2 days ago

We were 5 ladies and all of our dishes was fantastic…I had the 1/2 salad with Lemon Vinaigrette dressing on the side with a blackened piece of Salmon cooked to perfection! Ambiance was also beautiful with all the boats overlooking the restaurant

Red Fox Restaurant

4.5

4.5 (367)

$30 and under

Steakhouse

Middletown

About the restaurant

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!!!!

Top review

NicholasVIP

Dined 4 days ago

Very nice menu with good choices. Food delicious. Service could have been more attentive- didn’t seem that the restaurant was that busy. Nevertheless it was good an experience.

1741 Pub & Grill

4.5

4.5 (278)

$30 and under

American

Middlefield

About the restaurant

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.

Top review

Bill

Dined on May 9, 2025

The food was great, service was very good, they had a singer there, excellent voice and song choices. We will definitely go back.

Harrie’s Jailhouse - Middletown

4.5

4.5 (20)

$30 and under

American

Middletown

About the restaurant

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.

Top review

Jenny

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.

Dattilo Fine Italian at Water’s Edge

4.4

4.4 (901)

$31 to $50

Italian

Westbrook

About the restaurant

Located on the expansive grounds of the Water’s Edge Resort and Spa sits a beautiful restaurant with magnificent ocean views, Dattilo Fine Italian, the jewel of the Connecticut shoreline. The cuisine is fresh, creative and bold, with flavors reminiscent of old-world Italy. A rich authentic menu pairs with our extensive wine list features wines from across the globe. In addition to the seasonal menu Dattilo also offers nightly dining specials and themed dinners. Each Sunday we end the weekend with one of the finest Brunches in Connecticut featuring carving, pasta, crepe, and omelet stations. The brunch theme changes each week offering a new variety of fare to experience.

Top review

Abbi

Dined 5 days ago

Beautiful setting outside on the deck looking out into the water. Food was excellent and service was wonderful!

Surfridge Brewing Company

4.3

4.3 (53)

$30 and under

Pub

Centerbrook

About the restaurant

Wood fired Artisanal pizza and brewpub. Cold and hot share plates, Neapolitan Pies, and chef driven cuisine. House brewed beers, wines, mixology. Large patio, family and dog friendly.

Top review

pete

Dined on May 30, 2025

Surfridge Brewing Company is "THE BEST". The brewpub is located in an old industrial facility that has a ton of charm. The food and brew is top notch. They have regular specials ( which change with the seasons ) which are consistently outstanding. The Management team and Waitstaff are super friendly and engaging. We love coming here !!!! I highly recommend checking them out.

Fire at the Ridge

3.7

3.7 (808)

$31 to $50

Contemporary American

Middlefield

About the restaurant

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 music
Sunday brunch & outdoor Summer markets.

Check the event calendar at https://fireattheridge.com/ for weekly Live music and outdoor events.

Top review

Kurt

Dined on Jun 15, 2025

Great service and delicious food. Place was pretty empty and quiet. A very nice lunch.

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