Vermont Family Walking & Hiking Tour - 20s & Beyond

Fall in New England-Manchester to Woodstock

From $2,999 pp dbl. occ. | 5 days / 4 nights

Call for single supplement pricing

Whether the leaves are deep green or exploding in hues from yellow to red, breathtaking landscapes await you and your family. 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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Start/End Burlington

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

Vermont walking tour map


  • Discover the historic village of Manchester, where whitewashed homes are hemmed in by the rolling Green Mountains
  • Savor mouthwatering locally made 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
  • Explore picturesque Woodstock, a quintessential New England village, where quaint shops and storybook streets beckon

Start/End Burlington

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

Vermont walking tour map


Days 1-2 Learn the fine art of sugarmaking and taste maple syrup at Havoc Hill Sugar House | Hike through fern-laced hardwood forest below Mount Equinox and into the 900-acre Equinox Preserve, teeming with rare plants and diverse wildlife | Stroll through the Merck Forest & Farmland Center for sweeping vistas of the Taconic Mountains | Explore the historic village of Manchester.

Day 3 Take the morning to expore scenic Hildene—a bucolic estate with walking trails weaving through stunning meadows and forest, plus multiple historic buildings and a Georgian Revival mansion built by Abraham Lincoln’s son | Stroll through the famous Vermont Country Store on our way to Woodstock, where The Prince & The Pauper’s gourmet cuisine delights.

Days 4-5 Keep an eye out for wild turkeys while walking on historic carriage roads in Marsh-Billings-Rockefeller National 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 in the sprawling gardens and enjoy a farm-to-table dinner | Take in the amazing sight of molten forms crystallizing right before your eyes at a Simon Pearce demonstration—classic glassblowing craftsmanship is alive, well and stunning to behold.

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.

Please click on a date below for specific pricing and possible itinerary variations.

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F Family Dates - 20s and Beyond

Gather your favorite people to share a Backroads adventure on a ready-to-book Private Trip - featuring all the legendary Backroads hallmarks from expert leaders to unforgettable activities. You can pick from a large selection of dates for your group of 8 or more. Call us for date availability. If your party has fewer than 8 guests, or if your preferred date is not available, we'll create a departure just for you.

Private Trip Pricing
  • 10 or more Guests: from $2,999 pp dbl occ
  • 9 Guests: from $3,399 pp dbl occ
  • 8 Guests: from $3,599 pp dbl occ
  • 2-7 Guests: Give us a call or reach out here!

Don't see your ideal travel date? Make a Date

View Scheduled Dates

Tell us what your dream trip would be and we'll make it happen! Whether you're looking for a honeymoon trip for 2, a 30-person family reunion or a 100-person corporate trip, we can do it all. A dedicated Custom Trip Consultant will work closely with you to bring your dreams to reality. Call us at 800-462-2848 to speak with your Custom Trip Consultant or click on the button below.



F Family Tours - 20s and Beyond


From $2,999 pp dbl. occ.
5 days / 4 nights

Call for single supplement pricing

Premiere Hotels

Reluctant Panther Inn
Reluctant Panther Inn

Manchester Village (2 nights)

Woodstock Inn
Woodstock Inn & Resort

Woodstock (2 nights)

Activity Level

This trip is rated Levels 1-3

What's Included

Services and equipment are included.

Why Backroads

Why Travel with Backroads in Vermont

Reviews by Power Reviews ®

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Premiere Hotels

Accommodations may vary based on departure date. Any difference from what is listed below can be found by clicking on your desired date on the View Scheduled Dates or Private Dates tabs.

Reluctant Panther Inn

Reluctant Panther Inn

Manchester Village (2 nights)

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.

Woodstock Inn

Woodstock Inn & Resort

Woodstock (2 nights)

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)

This Trip Is Rated Levels 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.

Daily Route Options (drag to see full )

Daily Route Options
Level 1 Level 2 Level 3 Level 4 Level 5
miles feet gain miles feet gain miles feet gain miles feet gain miles feet gain
1 3 300 4 500
5 800
2 3 300 5 1000 6 1300
7 1800
3 3 100 4 400 6 400
4 4 400 5 600 6 700
5 1 200
2 400

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.

Learn more about how we determine our activity level and fully support a range of abilities and interests.

Please note that our distance and elevation figures come from Ride with GPS. Other sources may give differing elevation figures due to different GPS and mapping technologies and other external factors.


All breakfasts, 5 lunches, 3 dinners

Also Included

  • 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

Get the Straight Talk about This Trip

We want to make sure you're on the right trip and that you have the best experience possible. Every Backroads trip is unique and this one is no exception.

Why Travel with Backroads in Vermont

The Best Leaders in Vermont

Backroads has the best-qualified people to lead your trip in Vermont, and our guests back that up, rating our Trip Leaders an average of 9.75 out of 10 for all-around quality of performance. Get the facts (and no fluff) on how we recruit and develop the very best people for your trip.

Quality You Can Measure

Since 1979, Backroads Founder and President Tom Hale has shown that staying #1 means constantly evaluating our performance using the best possible source of information: our guests. As we systematically analyze your feedback on our trip consultants, leaders, hotels, meals and on-trip activities, we never stop working to make a great company even better.

Only the Best Hotels

On this trip featuring Premiere Hotels, you can count on the best lodgings Vermont has to offer. In fact, the hotels we've chosen in this region have higher retail room rates than those offered by any other active travel company—even when their trips cost more.

Everyone at Their Own Pace

We design and support our Vermont trips to suit mixed abilities and varied interests—so you can set your own pace, then change things up as the day unfolds. And all guests are free to do the same, traveling together or apart, with no one cramping anyone else's style. Which sounds easy in theory, but it's hard to pull off. Here's more on how we do it.

A Second Van When You Need It

Backroads is the only active travel company providing two support vans in Vermont—because we know it's essential to ensure a truly great travel experience. It doubles our ability to be there when you need us to offer hydration, lighten your load or give you a lift if it's time to take a break. Read more on why two vans make all the difference.

Signature Backroads Picnics

Guests rave about our picnic spreads. Enjoy a welcome break in a scenic spot, or a quick refuel stop if you don't want to lose momentum. And because we have two vans, one can host lunch while the other is out providing support along the route.

More Leaders to Support You

On our Vermont trips we have an extra leader supporting you along the trail—for a total of three, compared to the industry standard two. So we can be in more places at once, giving personal attention to guests traveling at their own pace. Here's more on our Trip Leaders.

Your Trip Will Run. Period.

Under our Book with Confidence policy, your Backroads trip will run even for one or two people (or a family of three or four), subject to a nominal extra fee. Or transfer to another trip, and we'll give you a credit. It's all part of our trademark commitment to treating guests with integrity, transparency and total accountability. Read all the details.

We Know Where We're Going

Tom Hale has been keeping Backroads on track, with one eye on the horizon, since 1979. His passion for active travel, and for ensuring the highest-quality travel experience, is evident in every detail we add to make a guest's trip unforgettable—and the fact he's right there in the office, making it happen. To hear Tom describe his vision, watch our video.  

Choose Your Fellow Travelers

With Backroads you won't end up with kids on what you thought was an adult trip; we have exclusive departures for families, so they're off having their own adventures. As you browse our unrivaled selection of trips and dates, you can count on finding a trip in Vermont that's geared exclusively to your choice of traveling companions.