15 Best Things to Do in Pittsfield (MA)

June 27, 2025

5 min read

Researched by Emily Roberts

Olivia Smith

Nestled in the picturesque heart of the Berkshire Mountains, Pittsfield, Massachusetts, is a vibrant city that often surprises visitors with its rich tapestry of culture, history, and natural beauty. Far more than just a stop on the way to other Berkshire towns, Pittsfield serves as a dynamic hub, offering an authentic New England experience brimming with artistic flair, outdoor adventure, and intriguing historical connections. Imagine strolling through a downtown alive with art, then moments later hiking a scenic mountain trail, or stepping back in time within a Shaker village.

This guide will unveil the 15 best things to do in Pittsfield, ensuring your visit is packed with discovery and delight. To make the most of your trip, consider visiting during the summer for vibrant arts festivals and outdoor activities, or in the fall for breathtaking foliage. Weekdays generally offer a more relaxed experience at popular attractions, but weekends often bring special events and a lively buzz. Get ready to explore a destination that truly has something for everyone.

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Herman Melville’s Arrowhead

Dive into the mind of a literary giant at Herman Melville’s Arrowhead, the very farmhouse where the author penned his magnum opus, “Moby Dick.” This historic property offers an unparalleled glimpse into Melville’s life and the inspirations behind his iconic works. You will explore the preserved rooms where he lived and wrote, feeling the palpable presence of history and creativity. The house is meticulously maintained to reflect its 1850s appearance, complete with period furnishings and personal effects that offer intimate insights into his daily life.

Step outside, and you are greeted by breathtaking, unobstructed views of Mount Greylock, a landscape that profoundly influenced Melville’s imagination and found its way into his narratives. Knowledgeable guides bring his stories to life, sharing anecdotes about his family, his struggles, and his creative process. It is not just a house tour; it is a journey into the literary past, perfect for history buffs, literature enthusiasts, and anyone seeking a tranquil, reflective experience. Consider visiting during the quieter weekday mornings for a more intimate tour.