Pittsfield, MA

A Food Writer's guide to Pittsfield, Massachusetts

Stephanie Gravalese

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Spread of tacos, rice beans and cheese, margaritas in a restaurant setting at Tito's in Pittsfield, MassStephanie Gravalese

Pittsfield is a city that has been a part of my life for many years. It is a great place to visit and live because it offers stunning natural beauty and because of the food. I've gathered a list of 10 small-town spots in Pittsfield you need to try while visiting or living there. These are the few of many so if you don't find your favorite spot listed, know that there's a lot more food news and info from Pittsfield coming your way. So whether you're visiting for business, on vacation, or looking for a meal out, plenty of dining options are available to keep you full and happy.

The Berkshires is a region known for its world-class art and culture, but it's also home to great food. From comfort food to vegan and vegetarian fare, you won't be disappointed by the culinary scene in the largest city in The Berkshires. 

This guide to the best restaurants in Pittsfield will come in handy when you want a bite to eat. The city of Pittsfield itself has seen quite a resurgence as of late, with new restaurants opening and much more on the way. As a result, the downtown area is home to many great options for dining out.

Located just over an hour from Albany and about two hours from Boston or Hartford, Pittsfield is great for a day trip or weekend getaway in western Massachusetts!

  1. If you're looking for the perfect cup of coffee, Dottie's Coffee Lounge is the place for you. You'll be hard-pressed to find an espresso drinker or foodie who does not love this place. This spot is excellent for a quick cup of coffee or to eat while in downtown Pittsfield.
  2. Suppose you want to mix craft cocktails and serve comfort food all in one, head over to Methuselah Bar & Lounge. It's a great spot before or after seeing a Barrington Stage Company show since it's conveniently located in the North Street area of Pittsfield.
  3. Ayalada is a must-visit spot for frozen yogurt lovers when you're in Pittsfield. Their rotating list of flavors is delicious, and they have boba! So stop by for a treat, where you can try any combination of flavors with any range of toppings.
  4. Something about Pittsfield is just perfect for coal-fired, thin-crust pizza. And the best way to get a slice of that perfect pizza is at East Side Café in Pittsfield. The stone oven pies are cooked with care, and you can choose your toppings or go for their Special with sausage, hot peppers, garlic, and mushrooms.
  5. Italian-American comfort food is what you'll find at family-friendly Mazzeo's Ristorante in Pittsfield. The Mazzeo family still owns and operates the restaurant, following a tradition of fresh pasta made daily from scratch. Its menu includes fresh pasta and other ingredients, such as eggplant parmesan tower, brick oven pizza, and popular daily specials.
  6. If you're a craft beer enthusiast, then you know that it's hard to find new beers to try. So if you live in Pittsfield, Massachusetts, and are looking for something new, don't stress! Chico's Wine and Spirits have got you covered. They have cases of all your favorite brews, but they also carry plenty of options from small breweries around the country.
  7. The Thrive Diner is the first plant-based diner in Pittsfield, Massachusetts. The diner focuses on providing fresh and flavorful food in a warm and inviting atmosphere—plenty of menu items to fit any vegan's diet. They source their ingredients locally and make many things in-house.
  8. Start your Saturday morning off right by visiting the Pittsfield Farmers Market. The market, which is open from 9 am to 1 pm on Saturdays, offers a wide variety of locally-grown produce, meats and cheeses, handmade goods, and plenty of friendly faces. It's a great weekend stop to stock up on fresh seasonal fruits and vegetables for that afternoon barbecue or snag some locally-made gifts for friends and family. And with plenty of produce available in late June, you won't want to miss out on the chance to pick up some delicious strawberries or asparagus!
  9. In a food guide to Pittsfield, there are some unmissable must-stops. One of those is King Cone, a little ice cream stand at the corner of King and Hancock Streets. It's an example of how sometimes less is not only more. It's all you need. This is especially when it comes to summertime snacking! It's just good ice cream that you can eat on a beautiful summer evening. Also, catch the free Downtown Pittsfield Farmers Market just steps away from King Cone on Saturday mornings!
  10. The Smokey Divas is a great takeaway spot just a few minutes from downtown Pittsfield. This female and multigenerational family-owned business serves up great smoked meats with various sides. You can pick from brisket, pulled pork, or chicken and sides such as macaroni and cheese, potato salad, and collard greens.

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Stephanie Gravalese is a writer and photographer based in upstate New York and western Massachusetts, where she writes about food, farming and the craft beer industry.

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