• America's Lake District
  • Western Mass Arts and Music
  • Mt. Greylock, Mahican-Mohawk Trail, Appalachian Trail
  • Stockbridge, North Adams, Lennox
  • Art museums, Shakers villages, Tanglewood (July only)
  • Overnight at Red Lion Inn and The Porches

The Berkshires used to be known as America's Lake District, reminiscent of the English Lake District, with low rolling hills, miles of deep green forest, and glistening lakes. It's a spot that has drawn artists and writers, like Hawthorne, Melville, and Thoreau, and attracted world class art collections, like Mass MoCA and The Clark. And then there is Tanglewood, the summer home of the Boston Symphony Orchestra. This really is a place where the arts come out to play. Our visit to this historically rich area captures as much of the incredible scenery and local culture as we can fit into 7 days. Following paved footpaths in town and old Indian trails through forests, fields, and wetlands, the trail leads through an area of outstanding natural beauty famous art museums, Shaker villages, and towns that have captivated visitors for centuries.

Latest News:

I've been to the Berkshires, but walking with The Wayfarers made it so much better.
Walk mostly on paved footpaths in towns and in the park, and on some challenging woodland paths.


US $3,975.00
Per Person, Double Occupancy
(Single Supplement US $695.00)
Our Wayfarers friends' Price is US $3,605.00


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Begins: North Adams
Ends: Stockbridge
Berkshires Arts Walk Map

Hotels - Where we stay

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What Is Included in the Price of My Vacation

  • Full-time services of two staff - a Walk Leader and Walk Manager
  • A backup vehicle for resting walkers and moving luggage
  • Comprehensive Travel Information Package and Reading List
  • Diverse itineraries with an emphasis on history, geography, culture, peoples, flora and fauna
  • Demonstrations, wine tasting, admissions to museums and historic sites
  • All ground transfers (ferries, cable cars, trains, etc.)
  • Maps and unique souvenirs to commemorate your trip
  • First-class accommodations with cultural and historical interest
  • All meals - with choices - (Special dietary requirements? No problem!)
  • Wine with dinner
  • On-trail snacks and refreshments
  • All gratuities at hotels and restaurants