Living Near Pittsfield

32 of the 101 towns sit within fifty driving minutes of Pittsfield, and roughly 7,429 people across the region already commute to work there. Minutes are town centre to workplace on open roads, without traffic, your street and your rush hour will differ.

Pittsfield, the point the drive times are measured to

Within 20 Minutes

Town	Drive	Median Home (Assessed)	Tax on Median	Wired Internet	Schools Through 12	Already Commute
Dalton Berkshire	12 min	$315,300	$5,319/yr	cable	yes	≈1,275
Lanesborough Berkshire	13 min	$309,850	$5,357/yr	cable	yes	≈615
Lenox Berkshire	16 min	$543,800	$5,488/yr	cable	yes	≈468
Richmond Berkshire	17 min	$531,400	$5,447/yr	cable	tuitions out	≈183
Cheshire Berkshire	20 min	$305,000	$3,227/yr	cable	yes	≈512
West Stockbridge Berkshire	20 min	$535,700	$5,629/yr	cable	yes	below the count floor

20 to 35 minutes

Town	Drive	Median Home (Assessed)	Tax on Median	Wired Internet	Schools Through 12	Already Commute
Lee Berkshire	22 min	$371,350	$4,208/yr	cable	yes	≈471
New Ashford Berkshire	24 min	$442,500	$2,505/yr	town fibre	tuitions out	below the count floor
Washington Berkshire	26 min	$336,450	$4,650/yr	town fibre	yes	below the count floor
Windsor Berkshire	26 min	$289,650	$2,731/yr	town fibre	yes	≈159
Stockbridge Berkshire	27 min	$702,200	$4,891/yr	cable	yes	below the count floor
Becket Berkshire	28 min	$328,200	$3,170/yr	town fibre	yes	≈172
Hinsdale Berkshire	28 min	$355,700	$3,781/yr	cable	yes	≈357
Adams Berkshire	29 min	$246,850	$3,858/yr	cable	yes	≈910
Peru Berkshire	29 min	$267,800	$4,309/yr	cable	yes	≈126
Hancock Berkshire	33 min	$352,600	$769/yr	cable	tuitions out	≈120
Tyringham Berkshire	34 min	$563,500	$3,736/yr	cable	tuitions out	below the count floor

35 to 50 minutes

Town	Drive	Median Home (Assessed)	Tax on Median	Wired Internet	Schools Through 12	Already Commute
North Adams Berkshire	37 min	$191,450	$3,057/yr	cable	yes	≈824
Savoy Berkshire	37 min	$207,950	$3,019/yr	cable	tuitions out	≈87
Cummington Hampshire	38 min	$330,000	$4,122/yr	town fibre	yes	below the count floor
Williamstown Berkshire	39 min	$466,450	$6,728/yr	cable	yes	≈201
Great Barrington Berkshire	40 min	$518,000	$7,024/yr	cable	yes	≈243
Clarksburg Berkshire	41 min	$211,100	$2,594/yr	cable	tuitions out	≈119
Worthington Hampshire	41 min	$350,300	$4,880/yr	cable	tuitions out	below the count floor
Plainfield Hampshire	42 min	$244,850	$4,300/yr	town fibre	yes	below the count floor
Alford Berkshire	43 min	$1,066,450	$4,340/yr	town fibre	yes	below the count floor
Chester Hampden	43 min	$214,100	$3,867/yr	cable	yes	below the count floor
Middlefield Hampshire	43 min	$234,550	$3,959/yr	cable	yes	below the count floor
Otis Berkshire	43 min	$449,300	$2,678/yr	town fibre	tuitions out	below the count floor
Monterey Berkshire	45 min	$620,850	$4,483/yr	no wired cable	yes	below the count floor
Chesterfield Hampshire	49 min	$360,500	$5,501/yr	town fibre	yes	below the count floor
Goshen Hampshire	49 min	$338,000	$4,700/yr	town fibre	yes	below the count floor

Reading This Honestly

Drive times are computed town centre to workplace over the open road network, free of traffic. A hilltown's own roads, snow, and rush hour all add real minutes.
Median home values are assessed values from the towns' own rolls, asking prices run different, usually higher.
"Already commute" counts come from the federal commute census, which counts jobs by workplace, small flows fall below its floor and show as such, never as zero.
"Tuitions out" means older students attend a neighbouring district by arrangement, every grade has a school.

Sources

Drive times over the open road network (OpenStreetMap); town assessment rolls and certified tax rates. Checked 2026-08-05.
Federal commute census (LODES). Figures through 2022.

"Figures through" is the period the publisher's data describes; "checked" is only when we last asked. The full sourcing: sources and method.