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Best Historic Restaurants in Cheshire

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46 restaurants available nearby

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A photo of Il Gusto Italian Wine and Bar restaurant
1. Il Gusto Italian Wine and Bar
4.5
Awesome(205)
$$$$
• Italian • Cheshire
Booked 19 times today
Welcome to Il Gusto Restaurant and Wine Bar, Cheshire's newest Italian dining experience, brought to you by restaurateur Gina Baca and Frederico Agraja, the chef and owner of the acclaimed Adriana's Restaurant and Wine Bar in New Haven. Situated at the historic location of the former Waverly Inn at 286 Maple Ave., Il Gusto revives a cherished local landmark, combining the rich heritage of its predecessor with the vibrant flavors of modern Italian cuisine. Il Gusto will feature a menu reminiscent of Adriana's, offering a delectable selection of traditional and contemporary Italian dishes. With seating for over 220 guests and a spacious banquet room, we are the perfect venue for dining, parties, meetings, and special events. Our goal is to preserve the history of the Waverly Inn by showcasing framed photographs of the original establishment, creating a warm and nostalgic atmosphere for our guests.
A photo of The Library Wine Bar & Bistro restaurant
2. The Library Wine Bar & Bistro
4.6
Exceptional(841)
$$$$
• American • Wallingford
Booked 14 times today
A UNIQUE DINING EXPERIENCEWe've combined the essence of historic downtown Wallingford with exquisite cuisine, along with a worldwide wine selection to bring you Wallingford's most unique dining experience.The Library Wine Bar and Bistro is Wallingford's original town library. Built in 1899, it was passionately and lovingly restored back to its classic, architectural beauty in 2014.Executive Chef Jonathan Harris, and the Massella family invite you to come and dive into a new chapter of an old Wallingford landmark. Savor the comforts of traditional cuisine, wine, and spirits while nestled at a comfortable table near our cozy fire, and let the story begin!
A photo of New Mill Restaurant restaurant
3. New Mill Restaurant
4.9
Exceptional(2052)
$$$$
• Contemporary American • Southington
Booked 28 times today
Plantsville's well-known Old Mill is now New Mill Restaurant, featuring the culinary talents of its new Executive Chef, Bob Martucci. This lovely 1737 cider mill has been a Connecticut favorite for many years, and has now completely renovated by its owners, Chris and Michelle Calvanese. Menu specialties include fresh-only seafood and raw bar selections, "chop house" Angus steaks, and homemade pastas and desserts. An expanded wine list and a large sociable bar round out the new offering.
A photo of Union League restaurant
4. Union League
4.8
Exceptional(2951)
$$$$
• French • New Haven
Booked 8 times today
Located across from Yale University and overlooking Yale’s Old Campus, Union League is a maison of French cuisine that brings together Old World charm, French classical traditions, and a contemporary approach to flavors, textures, and natural ingredients. Its chefs and culinary team create our award-winning cuisine with local and organic fish, meats, cheeses, produce, and rare specialty products from around the world. Tracing its lineage to the Union League Club founded in 1884, Union League continues to serve as the preeminent home of Connecticut’s special occasion and fine dining, sought out for its superb cuisine, acclaimed wine list, and professional staff and service.
A photo of The Griswold Inn restaurant
5. The Griswold Inn
4.5
Awesome(1106)
$$$$
• American • Essex
Booked 29 times today
The Griswold Inn is an inn and restaurant located in the historic seaport village of Essex. The Gris, as it is affectionately known, has been in continous operation since 1776.`Currently we are offering dine in, dine out, and Gris To Go! Inside, guests may enjoy dining in historic, art-filled rooms which exude character, charm and tradition. Seating for the alfresco experience is available on a first-come, first-served basis, with the exception of larger parties of 7 or more which may be made by calling 860.767.1776. The Inn boasts a wine list consistently recognized by Wine Spectator with the prestigious Award of Excellence; Food & Wine and Travel + Leisure have recently recognized the Inn's restaurant as "Connecticut's coziest" and it is included in Patricia Schulz's "1000 Places to See Before You Die". The Griswold Inn is also the recipient of Connecticut's Highest Award for Hospitality. The best of old and new meet here.
A photo of ZINC restaurant
6. ZINC
4.6
Exceptional(2980)
$$$$
• Contemporary American • New Haven
Booked 6 times today
Across from the historic New Haven Green, ZINC offers an innovative seed-to-plate menu that celebrates the surrounding community. Sustainable food has been the focus of ZINC since opening its doors in 1999 and has helped earn our place as a fixture in the downtown landscape. Our modern interpretation of “Globally Inspired Cuisine” is local market inspired and globally infused with a focus on sustainable food, offering a dining experience fit for the most enthusiastic of foodies. ZINC offers a Wine Spectator award-winning wine menu.
A photo of Diorio's Restaurant and Bar restaurant
7. Diorio's Restaurant and Bar
4.8
Exceptional(687)
$$$$
• Italian • Waterbury
Booked 10 times today
Please call the restaurant at 203-754-5111 for additional availability.The legendary history of Diorio Restaurant began in the 1920s. The late Rocco Diorio was responsible for the fine traditional food and many lasting memories for most of the people in the greater Waterbury area. The restaurant was closed in 1980 and reopened in 1991 after total restoration to its original splendor. The legend continues as we remain true to those endearing memories. We have the original marble bar, over-sized mahogany bankers booths, tin ceiling, and the most impressive acid-etched mirrors displaying historical Waterbury. Diorio Restaurant has once again reclaimed its reputation as Waterbury's finest.
A photo of Fleming's Steakhouse - West Hartford restaurant
8. Fleming's Steakhouse - West Hartford
4.7
Exceptional(1679)
$$$$
• Steakhouse • Hartford
Booked 52 times today
Your West Hartford Fleming's is located in the historic Educational Building, just off West Hartford Center and next to the Noah Webster Library. Fleming's in West Hartford is an outstanding choice to enjoy an exceptional Prime steak, glass of wine or handcrafted cocktail. Whether you're celebrating a special occasion, hosting a business dinner or simply wanting to enjoy a night out - we will create a safe and memorable evening in our Dining Room. If you prefer to enjoy your fine dining experience at home, you can order and pay for lunch or dinner online and then pick up curbside or select from one of our delivery partners.
A photo of The Charles - Wethersfield restaurant
9. The Charles - Wethersfield
4.5
Awesome(1968)
$$$$
• Contemporary American • Wethersfield
Booked 56 times today
Vintage Feel, Modern Taste – Welcome to The CharlesLocated in the historic Old Wethersfield, CT, The Charles blends timeless charm with contemporary cuisine. Whether you're dropping in for a craft cocktail and small bite at the bar, enjoying a fireside dinner, hosting a business meeting in our state-of-the-art Board Room, or celebrating a special occasion in our private dining room, The Charles offers an experience for every guest.As we proudly celebrate 5 years in June 2025, The Charles has earned over 70 awards for excellence in culinary innovation, beverage programs, service, ambiance, and community involvement.Come see why The Charles continues to be a local favorite and a destination dining experience.CT Magazine's 2025 Best RestaurantsStatewide Finalist▪ Business Lunch▪ Most Romantic▪ Wine SelectionStatewide Runner-Up▪ American New▪ Fine DiningHartford County Winner▪ American New▪ Fine Dining▪ Most RomanticCRA (2022)Best Restaurant – North Region
A photo of Steakhouse at Millpond Gathering restaurant
10. Steakhouse at Millpond Gathering
4.7
Exceptional(477)
$$$$
• Steakhouse • North Haven
Booked 6 times today
At Millpond Gatherings, we are an all encompassing hospitality center where you can eat, celebrate, shop, and stay with us here in the quaint town of Northford, Connecticut. The Millpond Steakhouse, run by Executive Chef Pedro Avila, is a farm-to-table modern American steakhouse with a fine dining flare. Our dry-aged grass fed beef is sourced from our own cattle farm just 2 miles up the road, and accompanied with local produce from our surrounding farmers. Downstairs in the Tavern we encompass the spirit of historic New England with a cozy laid back atmosphere and weekly live music on Thursdays and Sundays. Millpond Events is our venue hall located adjacent to the restaurant. This rustic charming space will harvest many special memories and celebrations.

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