• 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.

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Sunday Overnight: The Porches Inn

Meet at Albany International Airport and transfer to our hotel in North Adams, MA. We'll gather for a wonderful Welcome Dinner tonight.

Monday Overnight: The Porches Inn

Walk from our hotel to The Clark art museum, set on a 140-acre estate with views of the Taconic and Green Mountains. We'll stop to visit the fine collection and walk in the spectacular surroundings. After lunch we'll walk in the woods of Hopkins Memorial Forest, a thick leafy forest that cloaks the shoulder of the Taconic Range from ridgetop to valley.

Tuesday Overnight: The Porches Inn

This morning, a short walk leads to the internationally acclaimed Massachusetts Museum of Contemporary Art, or Mass MoCA, where we enjoy a guided tour. After lunch we'll savor the views of Mt. Greylock (the tallest mountain in Massachusetts) and the Hoosac Valley from a ridgetop trail. If time permits, we'll follow a network of suspended walkways to see the marble gorge at Natural Bridge State Park.

Wednesday Overnight: Red Lion Inn

Leave the hotel by van, and weather permitting we'll drive Rockwell Road over Mount Greylock and hike a bit of the Appalachian Trail. Otherwise, we'll walk at Field Farm, 300 acres of fields, woods and wetlands laced with miles of trails. Later, we visit Hancock Shaker Village, America's most successful communitarian society, now a living museum. Discover their unique approach to life and the remarkable fruits of their labor.

Thursday Overnight: Red Lion Inn

Today we explore Stockbridge, the beating heart of the Berkshires. Pass historic buildings, shops and galleries en route to the Norman Rockwell Museum for a visit. We'll also explore Chesterwood, the former estate of noted sculptor Daniel Chester French. After lunch in town, we'll make our way to the beautiful gardens of Naumkeag. This afternoon, explore the wonderful shops and galleries in town, or join us for a hike up to Laura's Tower that includes clambering over giant boulders in a glacial ravine.

Friday Overnight: Red Lion Inn

Begin today with theTyringham Shakers, the smallest of the Shaker communities. After tramping through a bucolic landscape of forest and farm we'll loop back on the Appalachian Trail over Tyringham Cobble overlooking the valley. This afternoon, we'll visit the modern art collection of the Frelinghuysen Morris House and Studio, and one final highlight in July, a walk in historic Lenox where we attend a concert at Tanglewood.


After breakfast The Wayfarers will transfer you to Albany International Airport.
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


12-JUL-20 - 18-JUL-20
04-OCT-20 - 10-OCT-20
Request booking
Begins: North Adams
Ends: Stockbridge
Berkshires Arts Walk Map

Hotels - Where we stay

The Porches Inn

The Porches Inn

Porches Inn, located across from the Massachusetts Museum of Contemporary Art in North Adams, was built from lovely 19th century Victorian row houses. The Porches Inns interior mixes modern design with an homage to the buildings history. A heated outdoor swimming pool, fitness center, Spa, and woodland gazebo are available for guests to enjoy. Each room has an Apple TV, Wi-Fi, and Jacuzzi tubs.
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn is an iconic Berkshires landmark with a 17-room guest house set in the center of Stockbridge, MA., decorated in the distinctive New England style. Hotel amenities include a heated pool, hot tub, restaurant and library. Each room has its own character and charm, and is well appointed with bathrobes and toiletries, flat screen TV and DVD player, Wi-Fi, alarm clock, hair dryer and luxury linens.

Start planning your trip

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