Pittsfield Muni (PSF)
Private Jet Charter

Stationed in the middle of the sprawling Berkshires, Pittsfield is proudly known as the “City of Festivals.” Ever since the first agricultural fair was held there in 1810, the area has always found a way to highlight its local achievements. 

Pittsfield has turned more towards the arts over the passing years. A designated cultural district, downtown Pittsfield is home to music, dance, theater and community festivals. The Berkshire Theatre Group and the Barrington Stage Company both put on compelling live performances. The art scene is also quite extensive with multiple galleries and artist studios in the area. The monthly First Friday Artwalk winds through Pittsfield; the self-guided tour showcases dozens of artists sharing their work.

Visitors can’t come to the Berkshires without taking in some of its natural beauty. Springside Park offers visitors 231 acres of hills, meadows and streams. In the spring and fall, visitors should listen closely to hear the migrating songbirds that stop to rest in the park. The park is also home to the Hebert Arboretum, a memory garden, and a lilac walk.

A jet charter airport in Pittsfield brings bibliophiles to Arrowhead, also known as the Herman Melville house. Melville wrote Moby Dick while at Arrowhead, which has been restored to its appearance at the time of Melville’s residence.

Downtown Pittsfield is full of small, one-of-a-kind shops and restaurants. Housewares, clothing, jewelry can all be found at the local retailers. Summertime farmer’s markets add an additional brightness to the area with flesh florals and local produce.