Berkshires & Catskills Hiking & Walking Tour
Couples, Friends & Solos
5 days
4 nights
Activity Levels 2-4
Deluxe Hotels
Berkshires & Catskills Hiking & Walking Tour
Couples, Friends & Solos
5 days
4 nights
Activity Levels 2-4
Deluxe Hotels
2026: Sep-Oct 2027: Sep-Oct
Woodstock, New England & the Appalachian Trail
Come play in the lovely valleys and summits of the Berkshires and Catskills, whose rich culture and history have left their stamp on the towns, art and music that were inspired here.
Highlights
- Hike picturesque landscapes of the Catskills and Berkshires, letting them envelop you with their regional charm and brilliant fall colors
- Ramble the iconic wooded Appalachian Trail and ascend Mt. Greylock in the footsteps of Thoreau
- Explore pleasant colonial towns, which have drawn artists and writers and where boutique shops and good music beckon
- Get a flavor of the dynamic local food movement and taste delicious seasonal edibles
- Stay in artsy hotels in the Berkshires and Woodstock, surrounded by natural beauty and the valley’s warm New England hospitality
Start/End Albany
* Start/End locations may vary. Do not book flights until your trip details are confirmed.
Itinerary
Days 1-2
Welcome to the Berkshires, a land that has inspired writers and artists for centuries! • Rich in culture and history, the region is lined with quaint towns, beautiful woodland and exquisite summer homes • Hike through the wooded trails around Mt. Greylock, the tallest mountain in Massachusetts, and drink in panoramic vistas of the valley • The mountain is said to have inspired such literary greats as Nathaniel Hawthorne, Herman Melville and Henry David Thoreau • Browse unique galleries, shops and cafés • Unwind at your riverside retreat, a hotel that evokes the classic American roadside motor lodge with a contemporary design.
Nights 1-2
This boutique riverside retreat was inspired by the classic American roadside motor lodge and is just the place to rest your head while visiting the Berkshires. (pool)
Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.
Days 3-5
Enjoy a guided tour of the renowned Clark Art Institute, home to world-class collections and stunning architecture • Taste handcrafted ciders and freshly made apple cider donuts on a guided tour of an orchard • The Band and Bob Dylan are legendary figures in these parts, drawing musicians to the powerful presence of the Catskills • Perhaps catch a performance on your own at Levon Helms Studio • Explore world-famous Woodstock surrounded by flowing creeks and lush woodland • Climb Overlook Mountain, the southernmost peak of the Catskill Escarpment and one that is central to Woodstock’s magic and mystique • Walk along a historic railroad of Rock Oak Land Preserve • Learn more about local craftsmanship in a live glassblowing demonstration at Woodstock Art Exchange • Rest your legs in our boutique hotel in Woodstock, an area known for attracting musicians, artists and bootleggers since 1787.
Nights 3-4
With peaceful surroundings and a conscious, modern design, this contemporary boutique hotel sits tucked behind a waterfall beside a babbling brook and has attracted musicians, artists and even bootleggers in its time.
Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.
What's Included
See moreDates & Prices
Dates & Prices
Click on dates to see pricing, hotel or itinerary variations and to book your trip. Price is per person, double occupancy, in USD.
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