The Berkshire Tour Plan and Itinerary

This is a combination trip. The first few days are a hub-and-soke tour, returning each night to the same hotel. The latter half of the trip involves riding to another part of the state, staying a couple of nights in another hotel, doing a hub-and-spoke tour from that hotel, and then returning to the first hotel before flying out.

Day One:

Fly to Albany, NY. Southwest Airlines allows bike travel cases to fly for $50 each way. All of the other airlines that service these two points charge between $125 and $150.

Rental Car:

Enterprise Rent a Car
Albany Airport
737 Albany Shaker Road
Albany, NY 12211-1001
(518) 785-7771

Travel time to hotel: One hour and fifteen minutes.

Stay at:
Days Inn Great Barrington
372 Main Street, Rte 7 and Main Street, Great Barrington, MA 01230
413-528-3150
$149/night

Reassemble the bike.


Day Two:

Bash Bish Falls 41 miles - returns to Great Barrington

This is a "must do" ride. The falls are beautiful. The route travels up Mount Washington and is quite steep at times. It also goes over a few sections of densely packed dirt and gravel road that are easily passable with a road bike.

The hike from the parking lot down to the falls is about 1/4 mile and quite rugged. Hiking shoes or tennis shoes are recommended. Bike shoes are not!


Day Three:

Stockbridge Loop 42 miles - returns to Great Barrington

Perhaps one of the most beautiful rides in the area. It passes through several towns and each is charming. Ride this route counterclockwise or face a very steep climb about 20 miles outside of Great Barrington.


Day Four:

Great Barrington to Williamstown 51.3 miles

Staying two nights in Williamstown, a beautiful little town in northern Massachusetts. I stayed at the Willows Motel because all other hotels in town were booked with families dropping off their children at the local college. I wouldn't recommend the Willows. It's too small and cramped for the money. Find another hotel.


Day Five:

Bennington Covered Bridges Loop 41.8 miles - Return to Williamstown.

Tour of three covered bridges in southern Vermont.


Day Six:

Williamstown to Great Barrington 47.1 miles - Return to Great Barrington.

Check back into the Days Inn for two additional nights.


Day Seven:

Layover in Great Barrington, rest, disassemble the bike and pack


Day Eight:

Fly home from Albany