Pittsfield trip planner
Create a fully customized
day by day itinerary for free
day by day itinerary for free
Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. It is the principal city of the Pittsfield, Massachusetts Metropolitan Statistical Area which encompasses all of Berkshire County. The population was 44,737 at the 2010 census. Although the population has declined in recent decades, Pittsfield remains the third largest municipality in western Massachusetts, behind only Springfield and Chicopee.In 2005, Farmers Insurance ranked Pittsfield 20th in the United States as "Most Secure Place To Live" among small towns with fewer than 150,000 residents. In 2006, Forbes ranked Pittsfield as number 61 in its list of Best Small Places for Business. In 2008, Country Home magazine ranked Pittsfield as #24 in a listing of "green cities" east of the Mississippi. In 2009, the City of Pittsfield was chosen to receive a 2009 Commonwealth Award, Massachusetts' highest award in the arts, humanities, and sciences. In 2010, the Financial Times proclaimed Pittsfield the "Brooklyn of the Berkshires", in an article covering its recent renaissance.In 2012, the city was listed among the 10 best places for single people to retire in the U.S. by U.S. News, due to the high number of single older residents and higher likelihood of finding companionship or a partner.Whether you only want to go to Pittsfield, or have a whole adventure planned, Inspirock has you covered with our user-friendly United States trip itinerary tool.
Create a full itinerary — for free!
Plan your trip to Pittsfield
Get a personalized tripA complete day by day itinerary
based on your preferences
Customize itRefine your trip. We'll find the
best routes and schedules
Manage itEverything in one place.
Everyone on the same page.
Popular things to do in Pittsfield
Side trips from Pittsfield
Hidden gems in Pittsfield
Nature in Pittsfield
Shopping in Pittsfield
Winter Sports in Pittsfield
Places to visit with Pittsfield
BostonTrip planner BEST FOR: Historic Walking Area, History Museum, Art Museum ProvincetownTrip planner BEST FOR: Beach, Dolphin / Whale Watching, Landmark CambridgeTrip planner BEST FOR: University / School, Landmark, Natural History Museum PlymouthTrip planner BEST FOR: History Museum, Monument, Historic Site SalemTrip planner BEST FOR: Nightlife, History Museum, Gift & Specialty Shop
Recently planned trips to Pittsfield
3 days in Berkshires BY A USER FROM UNITED STATES Pittsfield 14 days in Martha's Vineyard, Cape Cod & Berkshires BY A USER FROM UNITED STATES Edgartown Hyannis Provincetown 6 days in Massachusetts BY A USER FROM UNITED STATES Boston Salem Pittsfield 7 days in Pittsfield BY A USER FROM UNITED STATES Home of Franklin D. Roosevelt Vanderbilt Mansion National Historic Site The Dr. Oliver Bronson House 8 days in Pittsfield & Los Angeles County BY A USER FROM UNITED STATES Pittsfield Los Angeles 3 days in Berkshires BY A USER FROM UNITED STATES Pittsfield