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From Past to Present: Pittsfield’s Story

From Past to Present: Pittsfield’s Story
Camille Reddick
Camille Reddick
May 2, 2025

Are you about to plan an enchanted getaway to Pittsfield, MA? People around the country are drawn to Pittsfield and the rest of the Berkshires because they want to experience the gorgeous scenery, rolling views, wonderful shops and galleries, historic homesteads, and deep New England charm. While you've heard that Pittsfield is full of beautiful natural attractions and historic sites, you may not know much about the actual history of Pittsfield, MA. Here's a quick snapshot of how this quaint town became the fun, relaxing destination we know today.

A Glance at Pittsfield's Early Days

Pittsfield's Early Days

The Mohicans were an Algonquian people who inhabited present-day Pittsfield and the surrounding area until the 18th century. In 1738, a wealthy man from Boston named Jacob Wendell purchased 24,000 acres in what would eventually become Pittsfield. The area was known as Pontoosuck at the time. However, settling the land came with a slow start. What's more, Jacob Wendell would never actually live in Pittsfield. The men arriving to clear the land were interrupted by raids from the French and Indian War. It wasn't until settlers from nearby Westfield arrived in 1753 that real progress was made. In 1761, the place formerly Pontoosuck Plantation was officially named the Township of Pittsfield. Roughly 200 full-time residents called Pittsfield home at this time.

Pittsfield has become the home of many authors and artists over the years. Henry Wadsworth Longfellow, Oliver Wendell Holmes, and Herman Melville all had residences in Pittsfield at various points in their lives. Other notable Pittsfield residents have included Emily Robison of the Dixie Chicks, General Electric's Jack Welch, and Robin Williams.

Pittsfield's City Hall

Pittsfield's Growth

Pittsfield's population grew to 2,000 by the end of the Revolutionary War. The local economy was mostly agricultural at first. Over time, entrepreneurs in the textile, lumber, and grist fields took advantage of the many brooks throughout Pittsfield that flow to the Housatonic River. Pittsfield was also a leader in wool manufacturing for most of the 1800s and 1900s. While manufacturing has slowed down in Pittsfield, the great rise in industry during the 1900s left behind General Electric buildings that eventually became occupied by General Dynamics. In 2018, the ground broke on the new Berkshire Innovation Center, a hub for life sciences and advanced manufacturing.

Moments That Have Happened in Pittsfield Throughout the Years

Downtown Pittsfield

Pittsfield has had some big moments that have truly put this city on the map. There's one presidential moment in particular that American historians know well. In 1902, President Theodore Roosevelt passed through the Berkshires on a political tour when his carriage was struck by a speeding trolley on South Street in Pittsfield. While injured, Roosevelt survived. However, a secret service agent named William Craig became the first Secret Service agent to be killed in the line of duty as a result of the accident.

Pittsfield also had a major role in aviation history. In 1761, Pittsfield was the site of the first trial launch of a passenger-bearing balloon. In 1907, the city was officially declared the Aero Club of America's balloon ascent station.

One last fun piece of Pittsfield history trivia! Locals don't have to be that old to remember the famed Pittsfield Winter Carnival. Running from 1946 to 2008, this winter tradition attracted thousands of attendees with sled races, ice-fishing derbies, skiing tournaments, snow-sculpture contents, toboggan races, dog-sled races, and snowmobile races. Unfortunately, climate issues and logistics forced the Winter Carnival to end.

Experience Pittsfield in Person

While reading about the history of Pittsfield, MA, is one thing, exploring this charming New England city in person is unforgettable! There are also so many amazing restaurants and shops around town. In fact, this is the perfect place to stay if you're planning a trip to browse Berkshires antiques.