During my 15 years in the Berkshires, Pittsfield has been a city that’s grown on me the longer I’ve lived in the region. Over the past few years, I’m glad to have had a chance to meet with the chefs and people putting out food in the area. 

I put together a guide of some of my favorite food experiences for those visiting Pittsfield. Whether you’re in town to visit a relative, on a business retreat, or attending one of the many cultural events, there are plenty of options to have a good meal in the largest city in the Berkshires. 

Jump to:

• Coffee and desserts at Dottie’s Coffee Lounge
• Milkshakes at Joanne’s Pittsfield Luncheonette
• Cocktails at Methuselah Bar & Lounge
• Bread at Berkshire Mount Bakery Pizza Cafe
• Frozen yogurt at Ayalada
• Craft beer at Thistle & Mirth
• Tacos and margaritas at Tito’s Mexican Grille
• Pizza at East Side Cafe
• Eggplant Parmesan at Mazzeo’s Ristorante
• Craft beer to go at Chico’s Wine & Spirits
• Vegan Eats at Thrive Diner
• Everything local at the Downtown Pittsfield Farmers Market
• Soft serve at King Cone

Coffee and desserts at Dottie’s Coffee Lounge

Coffee & sweet treats at Dottie’s Coffee Lounge (444 North St, Pittsfield, MA 01201)

This North Street spot is the place to do in downtown Pittsfield for espresso drinks and sweet treats. I’m partial to sitting by the windows, but any seat is good.

Milkshakes at Joanne’s Pittsfield Luncheonette

A classic American diner in the Elm Street neighborhood of Pittsfield, this spot is not only a place to grab a short stack of pancakes but to grab a milkshake!

Cocktails at Methuselah Bar & Lounge

Located on Pittsfield’s North Street, this is the spot to grab a craft cocktail in downtown Pittsfield. A short walk from Barrington Stage Company, stop by Methuselah before a show or for a nightcap!

Bread at Berkshire Mount Bakery Pizza Cafe

While the bakery’s flagship location is in nearby Housatonic, the Pittsfield outpost is a spot where you can get all of the baked goods that Richard Boudon has to offer, including his famous Bread & Chocolate.

Frozen yogurt at Ayalada

Family-owned, and all the toppings! A short drive from downtown Pittsfield, grab a cone from their list of rotating flavors and top it with a range of sweet additions (from fresh fruit to boba and cereal!)

Craft beer at Thistle & Mirth

On the tail end of downtown Pittsfield, Thistle & Mirth offers about a dozen rotating taps, an extensive whiskey list, and more. A casual atmosphere, bring a group, grab some brews and settle around a board game for a fun night in the Berkshires!

Tacos and margaritas at Tito’s Mexican Grille

If you’re looking for a low-key spot for tacos and margaritas, Tito‘s is the place for you! They’re expensive lunch and menu options to offer something for everyone. Coming in for a weekday lunch? In my experience, the service has been quick and service friendly, and the food hot.

Pizza at East Side Cafe

The East Side Cafe is a Pittsfield landmark and one of the few places to get a coal-fired pizza. The Pizza toppings are simple — customers can build their own or go for the local’s favorite: The Special with sausage, mushrooms, garlic, and hot peppers. I’m a simple girl and go for pepperoni pizza all the way.

Eggplant Parmesan at Mazzeo’s Ristorante

Thin layers of eggplant are breaded and layered to make a small tower of sauce cheese that is the epitome of Italian-American comfort food. Eggplant parmesan is off of my favorite meals, and Mazzeo’s does it well.

Craft beer to go at Chico’s Wine & Spirits

Located on West Housatonic Street, Chico’s is worth a stop if you’re looking to stock up on your favorite brews for camping or want some craft beer recommendations while in Pittsfield.

Vegan Eats at Thrive Diner

While this is not the first time Pittsfield has had a plant-based restaurant, Thrive Diner is a good spot to know about if you are looking for vegan dining options in downtown Pittsfield. Sourcing locally as much as possible and making much of their food in-house is the place to grab a meal for those vegans in the Berkshires.

Everything local at the Downtown Pittsfield Farmers Market

Looking to stock up on local produce and meats and local vendors? Check out the Downtown Pittsfield Farmers Market, organized by Roots Rising. Occurring every Saturday in the summer with indoor options in the winter, Pittsfield’s farmers market features produce from local farmers all around the Berkshires, artisans selling their handmade wares, and live entertainment and activities for the family. As you can see from the photo, I’m a pretty big fan.

Soft serve at King Cone

Ice cream at King Kone (133 Fenn St, Pittsfield, MA 01201)

A short distance from the Farmers Market, King Cone is where you can get cheap soft serve on a warm summer night. This isn’t a place where you’ll find 50 different flavors: they keep it easy for good reason. Vanilla with sprinkles for me!

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