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Walking & Hiking
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Vermont Walking & Hiking Tour

Fall in New England—Manchester to Woodstock

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.

THIS ITINERARY: 5 days, 4 nights


FROM: $3,099 pp dbl occ
($800 for sgl occ)


Start/End Burlington

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

  • Explore the historic village of Manchester, where whitewashed homes are hemmed in by the rolling Green Mountains
  • Taste mouthwatering local maple syrup and learn the old New England art of sugarmaking
  • Wind your way through landscapes that envelop you in local charm and brilliant fall colors
  • Discover picturesque Woodstock, a quintessential New England village, where quaint shops and storybook streets beckon
The Backroads Experience
The Backroads Experience
Backroads Walking & Hiking Trips
Meet Our Leaders
Accommodations may vary based on departure date.
5 Days Premiere Hotels
Accommodations may vary based on departure.
Days 1-2

Taste maple syrup and learn the fine art of sugarmaking at Havoc Hill Sugar House | 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 stroll through the Merck Forest & Farmland Center reveals sweeping vistas of the Taconic Mountains | Explore the historic village of Manchester.

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

Spend the morning exploring scenic Hildene—a bucolic estate with walking trails weaving through stunning meadows and forests, plus multiple historic buildings and a Georgian Revival mansion built by Abraham Lincoln's son | Browse in the famous Vermont Country Store on our way to Woodstock, where The Prince & The Pauper's gourmet cuisine delights | 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 | Gentle switchbacks lead 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.

Woodstock Inn
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)

Dates & Prices

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

SMALL GROUP? TRY RENDEZVOUS | An extra leader and van for even more flexibility | Call us to book your Rendezvous.

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

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Activity Level: 1-3

Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. We know your pace may vary from one day to the next—and your traveling companion's may differ somewhat from yours. So we present a range of mileage options, and each day you decide exactly what and how much you want to do. LEARN MORE.

Day 1
Walking & Hiking
Level 1 | 3 miles | 300 ft. gain
Level 2 | 4 miles | 500 ft. gain
Level 2 | 5 miles | 800 ft. gain
Day 2
Walking & Hiking
Level 1 | 3 miles | 300 ft. gain
Level 2 | 5 miles | 1000 ft. gain
Level 3 | 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 | 4 miles | 400 ft. gain
Level 3 | 6 miles | 400 ft. gain
Day 4
Walking & Hiking
Level 1 | 4 miles | 400 ft. gain
Level 2 | 5 miles | 600 ft. gain
Level 3 | 6 miles | 700 ft. gain
Day 5
Walking & Hiking
Level 1 | 1 mile | 200 ft. gain
Level 1 | 2 miles | 400 ft. gain

Note: The terrain on this trip includes well-maintained forest trails, paved paths and dirt roads. 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.

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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