Berkshires & Catskills Walking & Hiking Tour

Couples, Friends & Solos

Small Group Adventures for:

Couples, Friends & Solos Adults 18+

Women's Adventures Women 18+

Families with Young Adults 20s & Beyond Best for ages 20+ (min. age 18)

Families with Teens & 20s Best for ages 16-23 (min. age 14)

Families with Kids & Teens Best for ages 7-17 (min. age 4)

5 days

4 nights

Activity Levels 2-4

We categorize our trips based on a range of activity levels from leisurely (1) to avid (5) with plenty of options in between.

Premiere & Deluxe Hotels

Premiere Hotels - Experience the world’s best, from lavish luxury to chic retreats with prestigious alliances.

Deluxe Hotels - Find modern comforts in extraordinary settings, with great ambience and ample amenities.

Casual Hotels - Known for their character, charm and proximity to outdoor adventures and Backroads activities.

Small Luxury Ships - Unpack once and cover more distance on an intimate ship with spacious staterooms and superb amenities.

Berkshires & Catskills Walking & Hiking Tour

Couples, Friends & Solos

Small Group Adventures for:

Couples, Friends & Solos Adults 18+

Women's Adventures Women 18+

Families with Young Adults 20s & Beyond Best for ages 20+ (min. age 18)

Families with Teens & 20s Best for ages 16-23 (min. age 14)

Families with Kids & Teens Best for ages 7-17 (min. age 4)

5 days

4 nights

Activity Levels 2-4

We categorize our trips based on a range of activity levels from leisurely (1) to avid (5) with plenty of options in between.

Premiere & Deluxe Hotels

Premiere Hotels - Experience the world’s best, from lavish luxury to chic retreats with prestigious alliances.

Deluxe Hotels - Find modern comforts in extraordinary settings, with great ambience and ample amenities.

Casual Hotels - Known for their character, charm and proximity to outdoor adventures and Backroads activities.

Small Luxury Ships - Unpack once and cover more distance on an intimate ship with spacious staterooms and superb amenities.

2025: Sep-Oct

From $3,399 - $3,449 /person

+8.13% Sales tax

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.

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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

New York

Start/EndAlbany

Airports & Travel details*

* Start/End locations may vary. Do not book flights until your trip details are confirmed.

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Itinerary

Days 1-2

Description

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.

Accommodations
TOURISTS

(2 nights)

Nights 1-2

TOURISTS
North Adams
*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 based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

Days 3-5

Description

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.

Accommodations
Woodstock Way

(2 nights)

Nights 3-4

Woodstock Way
Woodstock
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.

Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

Want to learn more about this trip?

Request a Detailed Itinerary! Complete with descriptions of each day, tips on travel arrangements, regional highlights and more, it’s the perfect tool to help you choose. You can easily share it with friends too!

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What's Included

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From $3,399 /person

+8.13% Sales tax

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Hotels

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

TOURISTS
North Adams

*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

Woodstock Way
Woodstock

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.

From $3,399 /person

+8.13% Sales tax

View Dates
Return

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From $3,399 /person

+8.13% Sales tax

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Dates & Prices

Click on dates for pricing, itinerary variations (if any) and to book your trip. Price is per person, double occupancy in USD.

Unplugged dates are perfect for guests who want to ride an acoustic bike.
E-bikes are available to travel companions by request only.

Your guest & room selections

1 adult

1 room, 1 bed

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Please Select a Group Size

Group size is required to show per-person pricing. Your group size can be approximate and can change.

Want to learn more about this trip?

Request a Detailed Itinerary! Complete with descriptions of each day, tips on travel arrangements, regional highlights and more, it’s the perfect tool to help you choose. You can easily share it with friends too!

Download & Share

Book with Confidence

Backroads provides flexible booking policies so that you can plan your vacation with complete peace of mind.

Learn more

From $3,399 /person

+8.13% Sales tax

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