Private charter · Pittsfield, MA
Private charter to & from Pittsfield
Fly private to Pittsfield, gateway to the Berkshires, for Tanglewood, summer theater and the hills of western Massachusetts
- PSF
- KAQW
- HCC
Price a private flight from Pittsfield
Fly private in Pittsfield
Pittsfield, without the hub.
- 3
- Airports
- 5
- Passengers
- 33
- Direct routes
Pittsfield is the largest city in Berkshire County and the practical center of the Berkshires, a region of wooded hills, lakes and small towns that has drawn summer residents from New York and Boston for well over a century. The city grew up around General Electric’s transformer and plastics operations, and today its economy relies on healthcare, plastics and defense manufacturing, and a cultural sector that includes the Colonial Theatre and the Berkshire Museum. Lenox, home of Tanglewood, and Stockbridge are a short drive south.
The Berkshires are close to both Boston and New York on a map but awkward to reach in practice, roughly three hours by car from either city, often in heavy weekend traffic. Flying private into Pittsfield Municipal Airport puts Lenox, Williamstown and the region’s inns and second homes within about half an hour. Summer visitors come for Boston Symphony Orchestra concerts at Tanglewood, Jacob’s Pillow dance, the Williamstown Theatre Festival and Shakespeare & Company, while fall foliage and winter skiing keep the region busy most of the year.
Airports
Charter to and from Pittsfield airports
Fly into whichever airport puts you closest to where you're going. Littlebird flies to and from these airports in and around Pittsfield, and the price is for the whole airplane, however many seats you fill.
PSF
Regional airportPittsfield Municipal Airport
Pittsfield · KPSF
- From downtown
- 3 mi
- Longest runway
- 5,792 ft
KAQW
Regional airportHarriman and West Airport
North Adams
- From downtown
- 17 mi
- Longest runway
- 4,300 ft
HCC
Regional airportColumbia County Airport
Hudson
- From downtown
- 26 mi
- Longest runway
- 5,350 ft
Top attractions
Things to do in Pittsfield
When to go. Summer is the Berkshires’ cultural high season, when Tanglewood, Jacob’s Pillow and the region’s theater companies run from late June through August. Fall foliage peaks in early to mid-October and fills inns on weekends. Winter brings downhill skiing at Jiminy Peak and Bousquet, along with cross-country trails, while spring can be muddy but quiet, with good deals on lodging.
- 01
Tanglewood
In Lenox, the summer home of the Boston Symphony Orchestra presents concerts in the open-sided Koussevitzky Music Shed and Seiji Ozawa Hall, with picnickers spread across the lawn.
- 02
Hancock Shaker Village
Just west of downtown, this living history museum preserves a former Shaker community, including its distinctive 1826 round stone barn, working farm and collection of Shaker furniture.
- 03
The Mount
Edith Wharton designed and built this Lenox estate in 1902, and its house and formal gardens are open for tours that explore her life, writing and ideas about design.
- 04
Mass MoCA
About 20 miles north in North Adams, a vast former factory complex holds one of the largest contemporary art museums in the country, along with performances and festivals.
- 05
The Clark Art Institute
In Williamstown, the Clark pairs a fine collection of French Impressionist and American paintings with walking trails across its hillside campus and views of the surrounding mountains.
- 06
Mount Greylock State Reservation
The highest point in Massachusetts rises north of Pittsfield, with a summit road, the Veterans War Memorial Tower, the Appalachian Trail and Bascom Lodge for meals and overnight stays.
Popular routes
Private flights from Pittsfield

Pittsfield Manchester
98 mi · about 35 min

Pittsfield Providence
103 mi · about 35 min

Pittsfield Boston
112 mi · about 40 min

Pittsfield New York City
126 mi · about 45 min

Pittsfield Burlington
140 mi · about 50 min

Pittsfield Stamford
98 mi · about 35 min

Pittsfield The Hamptons
115 mi · about 40 min

Pittsfield Newport
120 mi · about 40 min

Pittsfield Portsmouth
132 mi · about 45 min

Pittsfield Stowe
144 mi · about 50 min

Pittsfield Nantucket
181 mi · about 1 hr 5 min

Pittsfield New Haven
81 mi · about 30 min
Flights to Pittsfield
- Stamford98 mi · about 35 min
- New Haven81 mi · about 30 min
- New London96 mi · about 35 min
- Boston112 mi · about 40 min
- Nantucket181 mi · about 1 hr 5 min
- Martha’s Vineyard154 mi · about 55 min
- Hyannis162 mi · about 55 min
- Provincetown159 mi · about 55 min
- Worcester75 mi · about 25 min
- Plymouth136 mi · about 45 min
- Manchester98 mi · about 35 min
- Portsmouth132 mi · about 45 min
Every route from Pittsfield
- Manchester98 mi · about 35 min
- Providence103 mi · about 35 min
- Boston112 mi · about 40 min
- New York City126 mi · about 45 min
- Burlington140 mi · about 50 min
- Stamford98 mi · about 35 min
- The Hamptons115 mi · about 40 min
- Newport120 mi · about 40 min
- Portsmouth132 mi · about 45 min
- Stowe144 mi · about 50 min
- Nantucket181 mi · about 1 hr 5 min
- New Haven81 mi · about 30 min
- White Plains101 mi · about 35 min
- Hanover102 mi · about 35 min
- Westerly104 mi · about 35 min
- Martha’s Vineyard154 mi · about 55 min
- Killington86 mi · about 30 min
- Laconia118 mi · about 40 min
- Hyannis162 mi · about 55 min
- Montpelier130 mi · about 45 min
- North Conway154 mi · about 55 min
- Provincetown159 mi · about 55 min
- Buffalo287 mi · about 1 hr 40 min
- Worcester75 mi · about 25 min
- New London96 mi · about 35 min
- Rochester227 mi · about 1 hr 20 min
- Syracuse153 mi · about 55 min
- Montauk118 mi · about 40 min
- Lake Placid132 mi · about 45 min
- Plymouth136 mi · about 45 min
- Ithaca166 mi · about 1 hr
- Cooperstown87 mi · about 30 min
- Binghamton138 mi · about 50 min
Questions
Flying private in Pittsfield
Which airports can I charter a private flight to or from in Pittsfield?
Littlebird flies in and out of Pittsfield Municipal Airport (PSF), Harriman and West Airport (KAQW), and Columbia County Airport (HCC). Choose the one closest to where you're going; smaller regional airports usually mean a shorter walk from the car to the airplane.
How do I book a private charter from Pittsfield?
Enter your departure airport, destination, date and number of passengers above. You'll see an instant price for the whole airplane, with taxes and fees included, and you can book online in a few minutes.
How many passengers can fly on a charter from Pittsfield?
Up to 5 passengers, depending on the aircraft. You pay one price for the whole airplane, not per seat, so traveling together lowers the cost per person.
What are popular private flights from Pittsfield?
Popular trips include Manchester (about 35 min), Providence (about 35 min), Boston (about 40 min), and New York City (about 45 min). Every route is priced instantly online.
Is private charter in Pittsfield, MA safe?
Littlebird flights are operated under FAA Part 135 by Jetvia, in Cirrus aircraft that each carry a parachute for the entire airframe (CAPS).
More destinations in Massachusetts
Your next trip from Pittsfield starts here
Pick your airports, date and time, and see an instant price for the whole airplane, with taxes and fees included.
Get an instant price