The Berkshires & Hudson River Valley
Every day is 'choose your own adventure' -- whether that is antiquing, hiking, wine tasting... lots to discover!
- More about your Oliver Guide: Cynthia Pillsbury
- Trip type: Adult, City, Mountains
- Activity level: moderate
- Ideal length of trip: 5-7 days
to & from
We are on a road trip in our Sprinter Van, but easy to access this area by train (2 hours to Hudson) or via plane – Albany or West Hartford, CT. You will want a car to explore all the towns– so best bet to fly and then rent a car if you don’t live driving distance.
Where to Stay
We had a VRBO in Great Barrington, walking distance to town, which was important to us- it fit our needs. There are tons of VRBOs in the area. If you prefer a hotel, I would suggest The Maker Hotel in Hudson, NY or if you are staying more in the MA/CT area I would suggest The White Hart in Salisbury, CT or Little Cat Lodge in NY (all different states, but all close!) Lenox, MA has a ton of hotels- that town is top of my list for next fall! Some hotels that looked great… Doctor Sax House, Garden Gables and ofc Canyon Ranch.