Restaurants near Winchester Square

Restaurants in this area are known for American, Italian, Contemporary American, Fusion / Eclectic and Steak cuisines.

Some of the popular local menu items include Crab Cake Appetizers, Swordfish Special, Grilled Mahi Mahi, Home Fries and Lobster Bisque.

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77 restaurants available nearby

A photo of Cal Mare - MGM Springfield restaurant
1. Cal Mare - MGM Springfield
4.2
Awesome(206)
  • $$$$
  • Italian
  • Springfield, Massachusetts
Booked 7 times today

Phenomenal food and service. However heard they are changing over to a new type of restaurant they have in other MGM establishments across the country, called Costa. Anyway if you can get there before they make the change, do it. Best Caesar Salad ever. Excellent entrees. Fabulous desserts.

A photo of TAP - MGM Springfield restaurant
2. TAP - MGM Springfield
3.6
Very Good(10)
  • $$$$
  • Sports Bar
  • Springfield, Massachusetts

I was impressed with the food - the pulled chicken sandwich was really good and I'm usually disappointed with pulled chicken. Our waitress Yasmine was great & friendly, even when it was busy. The one thing that dampened our experience was check in at the front desk. We made reservations via Open...

A photo of Topgolf Swing Suite - MGM Springfield restaurant
3. Topgolf Swing Suite - MGM Springfield
4.1
Excellent(4)
  • $$$$
  • Sports Bar
  • Springfield, Massachusetts
Booked 1 time today

This place is amazing! Very clean and comfortable. Not just golf games as the name would seem to indicate, either. We played soccer, baseball, football, zombie dodgeball, carnival games, etc.! Very fun time, and we will definitely be back. We needed 1.5 hrs to get through the games we wanted to...

A photo of The Chandler Steakhouse - MGM Springfield restaurant
4. The Chandler Steakhouse - MGM Springfield
4.5
Awesome(178)
  • $$$$
  • Steakhouse
  • Springfield, Massachusetts
Booked 6 times today

It was exquisite!

A photo of 350 Grill restaurant
5. 350 Grill
4.0
Excellent(748)
  • $$$$
  • Steakhouse
  • Springfield, Massachusetts
Booked 9 times today

Centrally located in the Springfield Downtown Entertainment District. The 350 Grill restaurant is one not to miss. Fine dining at it best ! Excellent menu selection as well as a fully stocked bar. In an atmosphere that set the stage for a good night out.

A photo of Picks at The Sheraton Springfield restaurant
6. Picks at The Sheraton Springfield
2.4
(3)
  • $$$$
  • American
  • Springfield, Massachusetts
Booked 1 time today

Discover a wide variety of dining choices, ideal for relaxing with colleagues, clients, or friends. Start off at our renowned PICKS Restaurant.

A photo of Max's Tavern restaurant
7. Max's Tavern
4.4
Awesome(1963)
  • $$$$
  • American
  • Springfield, Massachusetts
Booked 31 times today

As always, the filet was magnificent, perfectly cooked to a 'medium rare' (or, as one waitress put it, 'rare plus') degree, and the mushrooms were equally great. Our guests had never been to the restaurant before, but instantly became new fans; their only non-complimentary comment was "It's rather...

A photo of The Student Prince Cafe restaurant
8. The Student Prince Cafe
4.3
Awesome(218)
  • $$$$
  • German
  • Springfield, Massachusetts
Booked 13 times today

Have never been disappointed by the Student Prince Cafe!!

A photo of Uno Pizzeria & Grill - Riverfront restaurant
9. Uno Pizzeria & Grill - Riverfront
5.0
Exceptional(1)
  • $$$$
  • Pizzeria
  • Springfield, Massachusetts
Booked 6 times today

Birthday for relative

A photo of Villa Napoletana restaurant
10. Villa Napoletana
4.5
Awesome(327)
  • $$$$
  • Italian
  • East Longmeadow
Booked 4 times today

Delicious food & attentive service. Enjoyed the atmosphere and the guitarist.

Dining around Winchester Square Hot Spots

Business area


  1. Old State House