Vermont Walking & Hiking Tour

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 1-3

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

Premiere 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.

Vermont Walking & Hiking Tour

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 1-3

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

Premiere 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 $3,699 - $3,799 /person

Fall in New England—Woodstock & Manchester

Whether the leaves are deep green or exploding in hues from yellow to red, breathtaking landscapes await. Hike along forest paths to covered bridges, sparkling rivers and mountain vistas. See stately homes and charming New England villages. From its famous maple syrup to postcard-worthy scenery, Vermont aims to please.

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Highlights

  • Discover the quintessential New England village of Woodstock, where quaint shops, fantastic restaurants and storybook streets beckon
  • Taste a variety of local specialties like cheese and mouthwatering local maple syrup and learn the old New England art of sugarmaking
  • Hike through picturesque landscapes that envelop you in local charm and brilliant fall colors
  • Explore the historic village of Manchester, where whitewashed homes are hemmed in by the rolling Green Mountains
Vermont Walking & Hiking Tour map

Vermont

Start/End Burlington

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

Explore Wright Park near the charming town of Middlebury • Watch for wild turkeys while walking on historic carriage roads in Marsh-Billings-Rockefeller National Historical Park • Sugar maples, 400-year-old hemlocks, bridges and wide-open pastureland make it a superb place to meander on foot • Hike gentle switchbacks to the top of Mount Tom and Mount Peg, with views of Woodstock below you as the Green Mountains rise in the distance • Take a gander at the sprawling gardens and enjoy a farm-to-table dinner • Just like magic! Molten forms crystallize right before your eyes at a Simon Pearce demonstration—classic glassblowing craftsmanship is alive, well and stunning to behold.

Accommodations

Nights 1-2

Woodstock Inn & Resort
Woodstock
Premiere Hotel

An "imposing landmark resort hotel facing the village green in a beautifully preserved village noted for its restored 18th-century homes," according to Andrew Harper. (pool, spa)

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

Days 3-5

Description

Taste maple syrup and learn the fine art of sugarmaking at Havoc Hill Sugar House • Admire local and international art at the Southern Vermont Arts Center on our way to Manchester • Walk through a fern-laced hardwood forest below Mount Equinox and into the 900-acre Equinox Preserve, teeming with rare plants and diverse wildlife • A hiking tour through Vermont's Merck Forest & Farmland Center reveals sweeping vistas of the Taconic Mountains • Explore the historic village of Manchester • Wander around scenic Hildene—a bucolic southern Vermont estate with walking trails weaving through meadows and forests, plus multiple historic buildings and a Georgian Revival mansion built by Abraham Lincoln's son.

Accommodations

Nights 3-4

Reluctant Panther Inn
Manchester Village
Premiere Hotel

A Zagat favorite, this sophisticated boutique hotel tucked in the mountains features a restaurant wine selection recognized by Wine Spectator. A Small Luxury Hotels of the World member.

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 $3,699 /person

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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

Woodstock Inn & Resort
Woodstock

Premiere Hotel

An "imposing landmark resort hotel facing the village green in a beautifully preserved village noted for its restored 18th-century homes," according to Andrew Harper. (pool, spa)

Nights 3-4

Reluctant Panther Inn
Manchester Village

Premiere Hotel

A Zagat favorite, this sophisticated boutique hotel tucked in the mountains features a restaurant wine selection recognized by Wine Spectator. A Small Luxury Hotels of the World member.

From $3,699 /person

View Dates
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From $3,699 /person

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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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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

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

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From $3,699 /person

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