Pittsfield, Massachusetts

Located in the heart of the Berkshires, Pittsfield is by far the largest city of the region and a cultural hub. Known as the “City of Festivals”, Pittsfield has a long history of fairs and celebrations, and there is seemingly always something going on in town no matter when you plan to visit, especially during the summer and fall months.

The Third Thursday celebration is one such event. Every third Thursday, from May through September, the city embraces the summer by closing off a large portion of North Street to host a massive street fair. There, you’ll find an endless selection of food vendors, art exhibitions, craft vendors, performances and much more!

But even if you’re not in town for one of the festivals, you’ll still find plenty of things to do on your visit. Being the largest city, Pittsfield has one of the most vibrant downtown districts in all of the Berkshires, with plenty of shops, entertainment venues, restaurants, galleries, and cultural attractions.

The Berkshire Museum is another must-visit when in town, and actually one of the biggest draws to the entire region! The renowned museum hosts a variety of exhibitions, combining art, science, and history to create an experience that the whole family will enjoy.

And if you’re a history buff, Arrowhead is the place for you. The former home of author Herman Melville is now a museum and the headquarters of the Berkshire County Historical Society, and you’ll find a variety of cultural and historical exhibitions when you visit.

But rest assured, if you’re finding yourself craving some peace and quiet out in nature after the hustle and bustle of the city, the Pittsfield State Forest has you covered. The 11,000-acre park offers visitors an abundance of hiking trails, cross-country skiing trails, and outdoor recreation. You can even bring your swimsuit and go for a swim up at Berry Pond, the highest body of water in the state!

There’s also the Canoe Meadows Wildlife Sanctuary, a 264-acre reserve of forests, wetlands, and fields, and the Bousquet Mountain ski area to hit the slopes during the winter months!

Pittsfield is a city that is bound to please nature lovers and city lovers alike. And with an endless list of things to do, see, and experience, a visit to the city makes for the perfect day trip (or two!) when staying with us here in Lenox. After all, the city is only 15 minutes up the road!