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Vermont Walking & Hiking Tour

Fall in New England—Woodstock to Manchester

Couples, Friends & Solos

5 days 4 nights

Activity Level: 1-3

Premiere Hotels

From: $3,599 - $3,749 pp dbl occ

($1,000 - $1,050 for sgl occ)

Whether the leaves are deep green or exploding in hues from yellow to red, breathtaking landscapes await on our Vermont Walking & Hiking Tour. 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.

Vermont Walking & Hiking Tour map
Vermont Walking & Hiking Tour map


Start/End Burlington

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


  • Discover picturesque Woodstock, a quintessential New England village where quaint shops and storybook streets beckon
  • Taste mouthwatering local maple syrup and learn the old New England art of sugarmaking
  • Hike through 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


Accommodations may vary based on departure date.
5 Days Premiere Hotels
Accommodations may vary based on departure.
Days 1-2

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 and Farmland Center reveals sweeping vistas of the Taconic Mountains | Visit the historic village of Manchester, known for its stately homes and manicured lawns | In the 1860s, Manchester was the vacation destination for Abraham Lincoln’s family | Spend the morning exploring scenic Hildene, a bucolic southern Vermont estate with walking trails weaving through stunning meadows and forests, and see multiple historic buildings and a Georgian Revival mansion built by Lincoln's son.

Exterior View of Reluctant Panther Inn
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.

Days 3-5

Taste maple syrup and learn the fine art of sugarmaking at Havoc Hill Sugar House | Browse the famous Vermont Country Store on our way to Manchester, perhaps purchasing a treasured souvenir | 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, drinking in the sight of Woodstock below you as the Green Mountains rise in the distance | Admire a bird's-eye view of storybook homes, steepled churches, the Middle Covered Bridge and the Woodstock Inn, all nestled amid the green and gold valley | Take a gander at the sprawling gardens and enjoy a farm-to-table dinner.

Exterior view of Woodstock Inn & Resort
Woodstock Inn & Resort
| 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)

The earlier you book, the more choice you'll have and the lower your price. And you can always change your mind — you won't be charged to transfer to a different trip before your final payment is due. View cancellation policy.

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

October 2023
Oct 2 - Oct 6
Sold out

Looks like you’re traveling with a smaller group

Our Private Trips are best for groups of 6 or more. We suggest joining a scheduled trip.

Please Select a Group Size

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

Activity Level: 1-3

Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. Several routes and a range of levels are offered each day so you can choose how much or how little activity you want to do. Learn more about how we determine activity levels.

Route notes

The terrain on this trip includes everything from well-maintained forest trails, paved paths and dirt roads to uneven, rooted paths covered with rocks.  Vermont's landscape is characterized by constant rises and valleys and the continuously rolling terrain can make the routes feel more challenging than the mileage may suggest.

Daily Route Options

Day 1
Walking & Hiking
Level 1 | 3 miles | 300 ft. gain
Level 2 | 4 miles | 600 ft. gain
Level 3 | 5 miles | 800 ft. gain
Day 2
Walking & Hiking
Level 1 | 3 miles | 300 ft. gain
Level 2 | 6 miles | 1300 ft. gain
Level 3 | 7 miles | 1800 ft. gain
Day 3
Walking & Hiking
Level 1 | 3 miles | 100 ft. gain
Level 2 | 5 miles | 400 ft. gain
Level 3 | 6 miles | 500 ft. gain
Day 4
Walking & Hiking
Level 1 | 4 miles | 500 ft. gain
Level 2 | 5 miles | 600 ft. gain
Level 3 | 6 miles | 700 ft. gain
Day 5
Walking & Hiking
Level 1 | 1 miles | 100 ft. gain
Level 1 | 2 miles | 400 ft. gain

What's Included

  • All breakfasts, 5 lunches, 3 dinners
  • Expertise and services of our experienced Trip Leaders
  • Snacks and beverages between meals
  • Additional guides and experts from the region on many trips
  • Van shuttles to support a variety of route options
  • Comprehensive Travel Planner with detailed pre-trip information
  • Private guided tours at museums, historic sites, wineries and other select attractions as noted in the Travel Planner
  • All gratuities at hotels and restaurants
  • Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
  • On biking and multi-adventure trips, use of fully equipped Backroads titanium bike plus helmet and accessories
  • Trailercycles, carriers, and kid-sized helmets for Family Trips
  • Equipment and experienced guides for kayaking, rafting, snorkeling, sailing and canoeing as described
  • Park and other entry fees
  • Fares for trains, ferries and other modes of travel as listed in the Travel Planner
  • Select coach transfers
  • Baggage transfers and porterage

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