Berkshires & Catskills Walking & Hiking Tour
Couples, Friends & Solos
5 days
4 nights
Activity Levels 2-4
Premiere & Deluxe Hotels
Berkshires & Catskills Walking & Hiking Tour
Couples, Friends & Solos
5 days
4 nights
Activity Levels 2-4
Premiere & Deluxe Hotels
2025: Sep-Oct
Woodstock, New England & the Appalachian Trail
Come play in the lovely moss-covered woodlands of the Berkshires and beautiful wilds of the Catskills. The rich culture and history have left their stamp on the quaint towns, the vibrant culinary movement and the art and music that were made here. The colorful wooded hills between New York and Massachusetts welcome you with wooded trails, panoramic mountain views and tasty farm-grown cuisine.
Highlights
- Hike picturesque landscapes of the Catskills and Berkshires, letting them envelop you with their regional charm and brilliant fall colors
- Explore pleasantly old-fashioned towns, where artisan shops, foodie-favorite restaurants and good music beckon
- Get a flavor of the dynamic local food movement of the Hudson Valley 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 and the Hudson Valley, 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 • Explore MASS MoCa, the world renowned contemporary art museum, and the Clark Art Institute • Browse unique galleries, shops and cafés • Unwind at your secluded riverside retreat, a hotel that evokes the classic American roadside motor lodge.
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)
Days 3-5
At the summit of Sugarloaf Mountain, pause for a moment to register the sweeping views of the valley • Follow a scenic trail through the Mountain Top Arboretum 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 • Perhaps catch a performance on your own at Levon Helms Studio • 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 • 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.
What's Included
See moreHotels
World-Class Hotels
Our hand-selected Premiere hotels offer exceptional hospitality and experiences as special as the regions we explore.
Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.
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)
Nights 3-4
Premiere 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.
Gallery
Dates & Prices
Dates & Prices
Click on dates for pricing, itinerary variations (if any) and to book your trip. Price is per person, double occupancy in USD.
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