
Vermont Walking & Hiking Tour
Vermont Walking & Hiking Tour
5 days
4 nights
Activity Levels 1-3
Premiere Hotels
2025: Sep-Oct

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.
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

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

Days 1-2
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.




Nights 1-2
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)

Days 3-5
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.





Nights 3-4
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.
What's Included
See moreHotels
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
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
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.
Gallery














#MyBackroadsTrip
Review Snapshot
by PowerReviews
Reviewed by 8 customers
Vermont Fall in New England Walking & Hiking Tour
We Really Enjoyed our Hiking trip in Vermont with Backroads! The Hikes were a variety each day and fun. I Loved walking through Farms, Estates, Preserves, and a State Park. The Group Leaders were Wonderful, Outstanding, and Accommodating. The Hotels were very Spectacular, Beautiful Rooms, wonderful breakfast each day, and nice locations. The dinners were delicious and Gourmet with nice ambience. The Lunches were creative and delicious and the group was Fun. I highly Recommend This Trip. It is a Unique and very Special Experience. Thank you Backroads!

First visit to Vermont did not disappoint.
This trip is perfect for exploring and getting a taste of Vermont. The scenery is beautiful and the Backroads experience is top notch. Our leaders, Jenny, Katie, and Brent were enthusiastic, knowledgeable, and very accommodating. The locations of the hikes had enough variety for all levels of hikers. Learning so much Vermont history and interesting facts was an added bonus. This trip left me wanting to visit Vermont again.


Huge Disappointment
The trip was disappointing and really no more special then if we visited Vermont on our own, except that it cost twice as much. Went in thinking this would be the first of many Backroads trips for us. The Backroads experience was a huge disapointment. Never again. Don't fall for the hype / marketing. Save your money.
Backroads Guest Services
Hi Robert, thanks for reaching out and for taking the time to share your feedback with us by phone and online. Our Vermont trip is known and loved for the food, foliage, and hotels (which we’re glad you enjoyed), but we can understand that you were underwhelmed with a trip that shares in the familiar Northeastern culture you have at home. As we discussed by phone, we also hoped this would be the first of many trips for you and do feel there may be a better trip suited to what you were looking for. Thank you again for sharing your experience with us.
Backroads Mission of Exceeding Expectations Met for Me!
Vermont's beautiful colors of fall AND the great variety of hikes through state and private park lands were a great gift of nature! Add the excellence of the tour leaders, luxurious accommodations, and dining delights and you have all the makings of a unforgettable trip... Having been on two Backroads hiking trips now, It is not hard to see why it is THE premier outdoor travel experience company!
Wonderful Trip
This was a fantastic trip! The tour leaders were awesome!
Fantastic trip to Vermont
We took the walking/hiking trip to Vermont and it more than lived up to our expectations. Our trip leaders were outstanding and upbeat. They made sure everyone was having a great time. The hikes, visit to Havoc Hill Sugar Shack, Simon Pierce glass blowing, Marsh-Billings- Rockefeller National Park , and Hildene were outstanding experiences. Now we are ready for another BackRoads Adventure.
Very enjoyable
The trip was everything I'd hoped for and more. Scenery was beautiful, colors were starting to change. I also enjoyed the added activities including glass blowing and trips to Hildene, Roosevelt home and learning how Vermont Maple Syrup is made. This was my 5th Backroads adventure and I can't wait for the next one!
Another Great Backroads Trip
Verified Buyer
Beautiful time of year in Vermont and walking the countryside made it even better. On every Backroads trip there have been excellent guides and this one lived up to the Backroads standard. Natalie and Quininen were top notch and lots of fun. They took great care of us. Tammy and I will never forget them. We felt like were traveling with two good friends. Highlights of the trip were Havoc Hill Sugar House where we leaved how to make maple syrup and how the sap to make they syrup is gathered. The Pogue, a 14 acre pond at summit of Mt Tom was a great view. Seeing the Marsh-Billings-Rockefeller Mansion all the displays were great. Especially enjoyed the railroad cars especially the one that Teddy Roosevelt campaigned for president from. Lodging was excellent but our favorite was the Reluctant Panther. Our room felt like it was designed especially for us. Overall the trip was excellent as all Backroad's are. With the standard set, every trip I've taken (is now 5) has been my favorite.
Dates & Prices
Dates & Prices
Click on dates for pricing, itinerary variations (if any) and to book your trip. Price is per person, double occupancy in USD.
Please Select a Group Size
Group size is required to show per-person pricing. Your group size can be approximate and can change.