Berkshires & Catskills Hiking & Walking Tour
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.
We rate our trips based on a range of activity levels from 1-5.
See this trip's Activity Options & Terrain for more details.
From $3,699/person
+8.125% Sales tax
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Snapshots from the Trip
Trip at a Glance
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 Mount 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
Sample itinerary. Trip details may vary by departure.
Start Albany Airport & Travel Details
- 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
Deluxe Hotel
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.
- Follow a scenic trail through the Hilltop Orchards and admire the beautiful landscaping of indigenous trees restored to their native Catskills home
- The Band and Bob Dylan are legendary figures in these parts, drawing musicians to the powerful presence of the Catskills
- Explore world-famous Woodstock with its Byrdcliffe and Maverick Art Colonies and unique shops and 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 the trails of the scenic Comeau property, taking in its natural beauty and peaceful surroundings
- Enjoy a fascinating glassblowing demonstration at the 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
Deluxe Hotel
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.
End Albany Airport & Travel Details
This trip has an activity level range of 2-4
All breakfasts, 5 lunches, 3 dinners
All accommodations on your Backroads trip
All gratuities at hotels and restaurants
Expertise and services of Backroads Trip Leaders
Lightweight carbon hiking poles
Backroads On Trip App with route maps, elevation profiles, daily snapshots and more
Additional local guides and experts, plus equipment for included activities as detailed in your itinerary
Exclusive activities, tours and cultural experiences, as detailed in your itinerary
All luggage transfers and porterage during your trip
Snacks and beverages between meals
Private cocktail and wine receptions on the first and last nights of your trip
Choice of Backroads t-shirt or hat, plus water bottle and luggage tag
Detailed Travel Planner with destination tips and pre-trip information
