![Large field of orange and green trees hit by the sun](/sites/default/files/styles/trip_gallery_full/public/2024/HDI-9_GCR_ST_24_001.jpg.webp?itok=XX7Srjo9)
![Open valley with large trees and patches of green grass](/sites/default/files/styles/trip_gallery_full/public/2024/BHDI-9_AST_ST_23_002.jpg.webp?itok=01KZI4Jf)
![Five guests hiking through forest.](/sites/default/files/styles/trip_gallery_full/public/2023/WILI_AOP_ST_22_077_VAR_0.jpg.webp?itok=zrtKRV9e)
![Apples dangling from branches of a tree](/sites/default/files/styles/trip_gallery_full/public/2024/BHDI_ALY_ST_22_015.jpg.webp?itok=FFGNPghv)
![Red barn next to an empty road](/sites/default/files/styles/trip_gallery_full/public/2024/BHDI-9_AST_ST_23_001.jpg.webp?itok=EaRlHtxE)
![Point of view shot of woman pouring wine in a (your) glass.](/sites/default/files/styles/trip_gallery_full/public/2023/MARIB_JNI_19_007.jpg.webp?itok=o3ihHCOQ)
![Wooden basket full of yellow fruits](/sites/default/files/styles/trip_gallery_full/public/2024/BHDQ_ALAMY_DT1941.jpg.webp?itok=GYV-WnEi)
![Moose in a field of dried grass](/sites/default/files/styles/trip_gallery_full/public/2024/HD_shutterstock_115695997.jpg.webp?itok=OGgsHO_d)
![River with large rocks and leaves scattered](/sites/default/files/styles/trip_gallery_full/public/2024/HD_shutterstock_1290028435.jpg.webp?itok=D0uzp5Pv)
![Bottom view of tall trees covered with yellow and green leaves](/sites/default/files/styles/trip_gallery_full/public/2024/HDI-9_GCR_ST_24_003.jpg.webp?itok=HZoupcnE)
![Woman sitting on a cliff with large trees on ground floor](/sites/default/files/styles/trip_gallery_full/public/2024/HD_shutterstock_1877448118.jpg.webp?itok=qLuFpxVW)
![Valley of yellow, green and red trees](/sites/default/files/styles/trip_gallery_full/public/2024/HD_shutterstock_1882160461.jpg.webp?itok=t5ppTwu-)
![Red bridge over a river](/sites/default/files/styles/trip_gallery_full/public/2024/HD_shutterstock_2346016491.jpg.webp?itok=DFBg2xqD)
![Sunset hitting a stone lighthouse](/sites/default/files/styles/trip_gallery_full/public/2024/HDI-9_GCR_ST_24_002.jpg.webp?itok=0hiV2lLz)
![Two guests with hiking gear walking down forest trail.](/sites/default/files/styles/trip_gallery_full/public/2023/MQBI_AST_ST_22_012.jpg.webp?itok=JCeWypwq)
Berkshires & Catskills Walking & Hiking Tour
Couples, Friends & Solos
From $3,399 - $3,449 /person
+8.13% Sales Tax
5 days
4 nights
Activity Levels 2-4
Premiere & Casual Plus Hotels
Berkshires & Catskills Walking & Hiking Tour
Couples, Friends & Solos
5 days
4 nights
Activity Levels 2-4
Premiere & Casual Plus Hotels
2025: Sep-Oct
![Large field of orange and green trees hit by the sun](/sites/default/files/styles/trip_gallery_full/public/2024/HDI-9_GCR_ST_24_001.jpg.webp?itok=XX7Srjo9)
![Open valley with large trees and patches of green grass](/sites/default/files/styles/trip_gallery_full/public/2024/BHDI-9_AST_ST_23_002.jpg.webp?itok=01KZI4Jf)
![Five guests hiking through forest.](/sites/default/files/styles/trip_gallery_full/public/2023/WILI_AOP_ST_22_077_VAR_0.jpg.webp?itok=zrtKRV9e)
![Apples dangling from branches of a tree](/sites/default/files/styles/trip_gallery_full/public/2024/BHDI_ALY_ST_22_015.jpg.webp?itok=FFGNPghv)
![Red barn next to an empty road](/sites/default/files/styles/trip_gallery_full/public/2024/BHDI-9_AST_ST_23_001.jpg.webp?itok=EaRlHtxE)
![Point of view shot of woman pouring wine in a (your) glass.](/sites/default/files/styles/trip_gallery_full/public/2023/MARIB_JNI_19_007.jpg.webp?itok=o3ihHCOQ)
![Wooden basket full of yellow fruits](/sites/default/files/styles/trip_gallery_full/public/2024/BHDQ_ALAMY_DT1941.jpg.webp?itok=GYV-WnEi)
![Moose in a field of dried grass](/sites/default/files/styles/trip_gallery_full/public/2024/HD_shutterstock_115695997.jpg.webp?itok=OGgsHO_d)
![River with large rocks and leaves scattered](/sites/default/files/styles/trip_gallery_full/public/2024/HD_shutterstock_1290028435.jpg.webp?itok=D0uzp5Pv)
![Bottom view of tall trees covered with yellow and green leaves](/sites/default/files/styles/trip_gallery_full/public/2024/HDI-9_GCR_ST_24_003.jpg.webp?itok=HZoupcnE)
![Woman sitting on a cliff with large trees on ground floor](/sites/default/files/styles/trip_gallery_full/public/2024/HD_shutterstock_1877448118.jpg.webp?itok=qLuFpxVW)
![Valley of yellow, green and red trees](/sites/default/files/styles/trip_gallery_full/public/2024/HD_shutterstock_1882160461.jpg.webp?itok=t5ppTwu-)
![Red bridge over a river](/sites/default/files/styles/trip_gallery_full/public/2024/HD_shutterstock_2346016491.jpg.webp?itok=DFBg2xqD)
![Sunset hitting a stone lighthouse](/sites/default/files/styles/trip_gallery_full/public/2024/HDI-9_GCR_ST_24_002.jpg.webp?itok=0hiV2lLz)
![Two guests with hiking gear walking down forest trail.](/sites/default/files/styles/trip_gallery_full/public/2023/MQBI_AST_ST_22_012.jpg.webp?itok=JCeWypwq)
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
![Berkshires and Catskills Walking and Hiking Tour map](/sites/default/files/styles/trip_page_map/public/2024/25_EA_WHDI9.jpg.webp?itok=60JkstcH)
Start/End Albany
* Start/End locations may vary. Do not book flights until your trip details are confirmed.
Itinerary
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_GCR_ST_24_003.jpg.webp?itok=7uynigyJ)
Days 1-2
Welcome to the Berkshires and the Hudson Valley, a land that has inspired writers and artists for centuries! • The valley stretches for 150 miles from the northern tip of Manhattan all the way to Albany • Rich in culture and history, the region is lined with quaint towns, beautiful woodland and exquisite summer homes • Walk 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 unique galleries, shops and cafés and taste delicious fresh apples and locally made cheese • Unwind at your secluded riverside retreat, a hotel that evokes the classic American roadside motor lodge.
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_24_TOURISTS_001.jpg.webp?itok=XjXypN1k)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_24_TOURISTS_003.jpg.webp?itok=64qGWlJI)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_24_TOURISTS_004.jpg.webp?itok=cTMl0ChI)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_24_TOURISTS_005.jpg.webp?itok=D5L69gO8)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_24_TOURISTS_006.jpg.webp?itok=kcbucPpR)
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)
![](/sites/default/files/styles/itinerary_533/public/2024/HD_shutterstock_2346016491.jpg.webp?itok=Ah4g441b)
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 up Hunter Mountain and take in the vistas of farmland, forests and rolling pastures • Rip Van Winkle is a legendary figure in these parts, dramatized in the stories of Washington Irving • Explore world-famous Woodstock, which still buzzes with "peace, love and happiness" and is filled with unique shops and surrounded by flowing creeks and lush woodland • Climb Overlook Mountain, the southernmost peak of the Catskill Escarpment and one that teems with rare plants and diverse wildlife • Rest your legs in our boutique hotel in Woodstock, an area known for attracting musicians, artists and bootleggers since 1787.
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_Woodstock-Way-Hotel_0252.jpg.webp?itok=L4E1iaSR)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_Woodstock-Way-Hotel_0096.jpg.webp?itok=_OPw0VIO)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_Woodstock-Way-Hotel_0136.jpg.webp?itok=Gqz8OKoK)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_Woodstock-Way-Hotel_0545.jpg.webp?itok=TLdsHLtJ)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_Woodstock-Way-Hotel_0662.jpg.webp?itok=9frL6k2z)
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.
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_24_TOURISTS_001.jpg.webp?itok=XjXypN1k)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_24_TOURISTS_003.jpg.webp?itok=64qGWlJI)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_24_TOURISTS_004.jpg.webp?itok=cTMl0ChI)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_24_TOURISTS_005.jpg.webp?itok=D5L69gO8)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_24_TOURISTS_006.jpg.webp?itok=kcbucPpR)
Nights 1-2
*Casual Plus 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)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_Woodstock-Way-Hotel_0252.jpg.webp?itok=L4E1iaSR)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_Woodstock-Way-Hotel_0096.jpg.webp?itok=_OPw0VIO)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_Woodstock-Way-Hotel_0136.jpg.webp?itok=Gqz8OKoK)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_Woodstock-Way-Hotel_0545.jpg.webp?itok=TLdsHLtJ)
![](/sites/default/files/styles/itinerary_533/public/2024/HDI-9_PR_Woodstock-Way-Hotel_0662.jpg.webp?itok=9frL6k2z)
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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