Private charter · KGNB → PSF
Winter Park to Great Barrington
1,692 miles. One price for the whole airplane.
Price your flight from Winter Park to Great Barrington
The trip
Winter Park to Great Barrington, door to door faster.
Trade about 35½ hours on the road for about a short flight in the air. Bluebird flies you direct from Granby Grand County Airport in Winter Park to Pittsfield Municipal Airport in Great Barrington, 1,692 miles in a private jet with two pilots up front. Need a different size of aircraft? We'll source one sized for the trip. The price is for the whole aircraft, with every fee and tax shown before you book.
- Distance
- 1,692 mi
- Flight
- —
- Driving
- 35½ hours
- Passengers
- Up to 1
Departing Winter Park
Airports in Winter Park
KGNB
Regional airportGranby Grand County Airport
Granby
- From downtown
- 16 mi
- Longest runway
- 5,001 ft
Arriving Great Barrington
Airports in Great Barrington
PSF
Regional airportPittsfield Municipal Airport
Pittsfield · KPSF
- From downtown
- 16 mi
- Longest runway
- 5,792 ft
HCC
Regional airportColumbia County Airport
Hudson
- From downtown
- 19 mi
- Longest runway
- 5,350 ft
When you land
Things to do in Great Barrington
Great Barrington is the main town of the southern Berkshires, a compact downtown of restored brick buildings, independent shops and restaurants set along the Housatonic River. Much of its economy depends on the second-home owners, weekenders and remote workers who have turned the surrounding countryside into one of the most desirable corners of New England, along with farms, small food producers, real estate and the arts. Bard College at Simon’s Rock and the Mahaiwe Performing Arts Center add a cultural life that lasts well beyond summer.
- 01
Mahaiwe Performing Arts Center
A restored 1905 theater on Main Street presents concerts, dance, comedy, film and live opera and theater broadcasts throughout the year.
- 02
Monument Mountain
Just north of town, popular trails climb to a rocky quartzite summit with sweeping views of the southern Berkshires; Herman Melville and Nathaniel Hawthorne famously hiked here together in 1850.
- 03
Bash Bish Falls
Near Mount Washington in the state’s far southwest corner, the tallest single-drop waterfall in Massachusetts plunges through a granite gorge into a clear pool.
- 04
Norman Rockwell Museum
In nearby Stockbridge, the museum holds the world’s largest collection of Rockwell’s original art, along with the studio he used, moved to the museum grounds.
- 05
Butternut and Catamount
Two family-friendly ski areas sit close to town, with Catamount straddling the New York state line and offering night skiing and a summer aerial adventure park.
- 06
Ashintully Gardens
In Tyringham, the Trustees maintain a contemplative mid-century garden of terraces, fountains and lawns created by composer John McLennan beside the ruins of an early 20th-century marble mansion.
Questions
Winter Park to Great Barrington flights
How long is a private flight from Winter Park to Great Barrington?
About a short flight in a private jet, for 1,692 miles direct. Driving the same trip takes about 35½ hours.
Which airports do flights from Winter Park to Great Barrington use?
You can depart from Granby Grand County Airport (KGNB) and arrive at Pittsfield Municipal Airport (PSF) or Columbia County Airport (HCC). Pick whichever is closest to where you're starting and where you're headed.
How much does a private charter from Winter Park to Great Barrington cost?
The price depends on the date, departure time, aircraft and where the airplane is positioned. Enter your trip above to see an instant price for the whole airplane, with every tax and fee included.
Can I book a round trip between Winter Park and Great Barrington?
Yes. Choose round trip when you search, and pick your return date and time. Flights from Great Barrington back to Winter Park are priced the same way.
Return flight
Great Barrington to Winter Park
More flights from Winter Park
More flights to Great Barrington
Explore Winter Park private charter and Great Barrington private charter, airports and things to do. Arriving at Pittsfield Municipal Airport (PSF).
Winter Park to Great Barrington, on your schedule
Choose your departure time and see a price for the whole aircraft. Bring up to 1 passengers for the same price.
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