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Biking Southern Vermont: A New England Idyll

Scenic biking routes through Southern Vermont lead us along quiet roads lined with maple trees, family farms, picturesque lakes and through quaint villages like Grafton and Woodstock, the essence of small-town New England charm.

  • Activity Level: Easy / Moderate
  • Daily Mileage: 10 - 37 mi
  • Daily Biking: 2 - 4 hr
  • Small Groups: 20
  • Biking
  • Easy / Moderate

Why You'll Love This Tour


Biking Southern Vermont: A New England Idyll

The rolling hills and verdant pastures of bucolic Windsor County provide an exquisite backdrop as you cycle through the pristine Vermont countryside. We’ll be immersed in the mountain lifestyle where hard-working Vermonters live off the land and devote their lives to making delectable goods from pure maple syrup to award winning artisanal cheeses and locally made craft beer. Along the way we’ll tour the boyhood home of Vermont-born President Coolidge, learn about the forefather of environmental sustainability, and stay in the historic Woodstock Inn, located just steps from one of “America's Best Main Streets”.

Cultural Highlights

  • Explore the gardens and grounds at the Marsh-Billings-Rockefeller National Historic Park and tour environmental innovator George Perkins Marsh’s boyhood home.
  • Sample maple syrup at a local sugarhouse and learn how sap from a Sugar Maple Tree is transformed into “liquid gold”
  • Enjoy the comforts of the Woodstock Inn, named of one of the 500 World’s Best Hotels by Travel + Leisure in 2015
  • Visit a Presidential Homestead and hear the story of how Calvin Coolidge became our 30th President in the living room of his boyhood home
  • Cycle past North Chester's famed Stone Village, a quintessential Vermont community of houses built from locally-sourced granite
  • Sip award-winning beers at one of Vermont’s most well-known craft breweries

What To Expect

This tour offers a combination of easy terrain mixed with moderate hills and is ideal for both beginning and experienced cyclists. Our VBT van support shuttle is always available for those who need assistance.

Average Daily Mileage: 10 – 37 miles
Average Cycling Time: 2 – 4 hours

Climate Information

Average Daily Temperature (°F) – Woodstock
May 68°  Jun 77°  Jul 81°  Aug 79°  Sep 72°  Oct 58°

Average Rainfall (in.) – Woodstock
May 3.8  Jun 3.4  Jul 4  Aug 3.6  Sep 3.6  Oct 4.5

What’s Included:

  • 5 nights in historic inns
  • 11 meals – 5 breakfasts, 3 lunches, 3 dinners
  • FREE use of our custom VBT bicycle and helmet
  • Service of two VBT Trip Leaders
  • Daily route directions and maps
  • Welcome reception
  • Sightseeing and cultural activities
  • Transfers
  • Admission to the Vermont Institute of Natural Science
  • 5% Frequent Traveler Credit to use on your next VBT vacation
  • Special Good Buy Discount
  • AND the option to add our Low-Cost Trip Extension: Pre-trip: Norwich-Hanover – 2 nights for only $345
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Land Only Single Supplement: $645

Please note: Web Special savings cannot be combined with any other offer. Standard Terms & Conditions apply when purchasing this trip. 2016 Prices include all airline surcharges and Government taxes and fees. Ask our Tour Consultants for details. Every effort has been made to produce this information accurately. We reserve the right to correct errors. Prices are based on preferences selected above, including meals and sightseeing as specified in What’s Included. All prices are subject to change. Departure dates and prices shown may be updated several times daily, and apply to new bookings only.

Itinerary & Map
Or, Expand All Days
DAY 1: Transfer from Hanover, New Hampshire / Warm-up ride in Grafton, Vermont

VBT will include a transfer from Hanover, New Hampshire, to the first inn on our tour, and back to Hanover at the conclusion of the tour.

Our transfer leaves from the bus stop located between The Hanover Inn and The Hopkins Center on Wheelock Street in Hanover, NH at approximately 1:15 pm. Please look for a representative holding a VBT sign. The shuttle will be coming from our pre-trip hotel with VBT guests. Please allow for traffic delays.

If you arrive after this time, you will need to arrange for transportation to The Grafton Inn at your own expense. Travel time from Hanover to Grafton is approximately 75 minutes, depending upon traffic.

If you are driving to the start of the tour, we recommend that you park your car in Hanover, New Hampshire, and join our included shuttle to the start and from the finish of the tour. The Parking Garage at 7 Lebanon Street allows for a stay of multiple days, with a charge of $15 per day. The garage accepts cash, credit cards and checks as payment. Note that the garage is not staffed on Sundays, the gate is up, and tickets are not issued. You will need to advise the staff on your return that you left your car on Sunday and do not have a ticket.

VBT Pre-Trip Extension guests: You have another morning to enjoy Norwich at leisure. At 1:00 pm, the shuttle will meet and transfer you to The Grafton Inn. Your shuttle bus driver will be holding a VBT sign. The shuttle will stop in Hanover, New Hampshire, to collect other VBT guests. Travel time from Norwich to Grafton is approximately 90 minutes, depending on traffic.

At The Grafton Inn, settle in and relax until 3:30 pm, when your VBT Trip Leaders will hold a safety and bike-fitting clinic, followed by a short warm-up ride. This evening, enjoy a welcome reception featuring artisanal cheeses from Grafton Village Cheese, followed by dinner at our inn.

Hotel: The Grafton Inn
Meals: D
Daily Options: 11 miles

DAY 2: Saxton River / Vermont Country Store / Chester Village / Swimming Pond

After a hearty breakfast, we’ll begin biking south and then east, crossing our first two covered bridges of the week. You may choose to take a break from biking with a stop into the family-owned Vermont Country Store in Rockingham. Known as the purveyor of practical and hard-to-find items, shopping here can be a bit like visiting Great Aunt Agatha’s home. Be sure to save some room in your bike bag for your favorites from the store’s great penny candy offerings. Ride past Brockway Mills to see the gorge and the small hydroelectric plant.

Next, you’ll have the chance to venture inside a “sugar house,” where we’ll discover how maple syrup is made; Vermont is the nation’s largest producer. Though the sap won’t be running during our cycling season, our visit here is sure to be illuminating, and we’ll also have the opportunity to purchase a tasty souvenir. Then we arrive in Chester in time for lunch.

Back in Grafton, there is time for a refreshing dip in the nearby swimming hole before we meet with a friendly, in-the-know local to hear all about cheese production in Vermont and the Windham Foundation—a non-profit established in 1963 to promote the vitality of Grafton and other rural Vermont communities.

For dinner on your own tonight, you can opt for casual dining at the Phelps Barn Pub, or enjoy the candlelit ambiance of the Old Tavern Restaurant.

Hotel: The Grafton Inn
Meals: B, L
Daily Options: 21 or 28 miles

DAY 3: North Chester's Stone Village / Stoughton Pond / Echo Lake

Today you’ll have the opportunity to ride past North Chester’s Stone Village. On the National Register of Historic Places, this community of homes built from locally-sourced granite is quintessential Vermont.

Continuing along our route, we’ll ride over the Springfield Dam. We’ll stop to enjoy a picnic lunch, prepared by our Trip Leaders, at the delightful Rockledge Farm. Here, you’ll have an opportunity to meet the artisans and see how Vermont hardwoods are crafted into stunning utensils, serving boards and furniture. Afterwards, continue cycling towards our inn, The Inn at Water’s Edge. Take a seat in a rocker and enjoy the inn’s location overlooking quiet Echo Lake.

We’ll have dinner tonight at our charming inn, run by our infinitely capable and personable innkeepers, Tina and Bruce Verdrager. Before retiring for the evening, you may wish to stop in the inn’s English pub for a local microbrew and game of billiards or darts.

Hotel: The Inn at Water’s Edge
Meals: B, L, D
Daily Options: 22 or 29 miles

DAY 4: Calvin Coolidge Homestead / Long Trail Brewing Company / Woodstock

After breakfast, we’ll pedal to the Calvin Coolidge Homestead in Plymouth Notch. During our visit at the Calvin Coolidge Homestead, we’ll hear the story of how Calvin Coolidge was sworn in here—his boyhood home—as America’s 30th President, on August 3, 1923. We’ll also visit the Plymouth Cheese Factory, which was established by the President’s father, John Coolidge, in 1890.

This afternoon, we visit the Long Trail Brewing Company, and enjoy lunch along with a sampling of this fine institution’s award-winning craft beers. We then ride along a quiet back road into Woodstock.

Ladies’ Home Journal named Woodstock “The Prettiest Small Town in America”—and we’ll discover why it’s so special during our two-night stay at Laurance Rockefeller’s delightful Woodstock Inn.

After a day of biking, you may choose to visit the inn’s spa this evening. Later, our Trip Leaders can offer recommendations about which of our inn’s three restaurants to try for a delicious dinner on your own.

Hotel: The Woodstock Inn & Resort
Meals: B, L
Daily Options: 22 or 28 miles

DAY 5: Quechee Village / Simon Pearce Glassblowing Center / Quechee Gorge / VINS

Today we cycle a quiet road alongside the Ottauquechee River to Taftsville and charming Quechee Village. There is a lot to see today, including the Simon Pearce Glassblowing Studio (which boasts an excellent on-site restaurant); Quechee Gorge, which you’ll have the opportunity to explore during an optional hike; and the Vermont Institute of Natural Science (VINS), admission to which is included in the cost of your trip. We also pass through two more of Vermont’s historic covered bridges.

There is a fantastic option for those looking for more mileage in the afternoon by riding a loop from Woodstock through Pomfret and West Hartford, before rejoining the group in Quechee. This route features some of the most spectacular scenery of the week, but does have some significant hills.

Those looking for a break from their bike may spend additional time in Woodstock, perhaps opting for a walk to the nearby Billings Farm & Museum or Marsh-Billings-Rockefeller National Historical Park. Admission to each site is included in the cost of your trip.

And don’t forget that our resort offers golf, a yoga studio, indoor swimming pool and 12 tennis courts.

Hotel: The Woodstock Inn & Resort
Meals: B, D
Daily Options: 20 or 32 miles

DAY 6: Mount Tom walk / Depart for home

This morning, we’ll cross our last covered bridge of the week—on foot, this time, as we embark on a walk from our inn. Our route through the town’s Billings Park is up a switchback trail to the summit of Mount Tom, which offers a panoramic view of Woodstock village. What a fitting last glimpse of this spectacular landscape! We continue walking along the carriage trails of the Marsh-Billings-Rockefeller National Historical Park, ending at the park’s visitor center and the Billings Farm & Museum.

The tour concludes back at The Woodstock Inn & Resort. Checkout time is 11:00 am and you may store your bags with the inn. VBT has made arrangements for a shuttle from the inn back to the bus stop in front of The Hanover Inn in Hanover, New Hampshire. It departs Woodstock at 1:00 pm. Travel time is approximately 40 minutes, depending on traffic.

Meals: B
Daily Options: Non-riding day (2.5 mile walk)

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The Inn at Water's Edge

The Inn at Water’s Edge is quietly nestled between the lovely and serene Echo Lake and the rippling waters of the Black River. This authentic and inviting 150-year-old Victorian estate has been thoughtfully restored by its owners and innkeepers to ensure that it retains all the charm and ambiance of a truly unique Victorian inn. The Inn is a member of the Select Registry and is a AAA Four Diamond Inn.
Free WiFi Included

The Grafton Inn

The Grafton Inn is one of the oldest operating inns in America, having opened its doors in 1801. Located in historic Grafton, Vermont, the inn is a member of the non-profit Windham Foundation, which is dedicated to preserving the vitality of Vermont’s rural communities. Every stay helps to fund the Foundation’s many philanthropic programs. The Grafton Inn is proud to be a member of Historic Hotels of America, Distinctive Inns of New England, the Vermont Fresh Network and Green Hotels of Vermont. The village of Grafton is a member of the National Register of Historic Places.
Free WiFi Included

The Woodstock Inn & Resort

The Woodstock Inn & Resort is a charming luxury resort hotel set against a backdrop of breathtaking scenery ideal for enjoying New England’s finest cultural and sporting activities. The resort’s facilities include a Golf Club and a 41,000-square-foot Racquet & Fitness Club. In September 2010, the Resort opened The Spa at Woodstock Inn & Resort, featuring locally inspired treatments and products. There are three restaurants within the inn.
Free WiFi Included

The Norwich Inn

The Norwich Inn is an historic, full-service country inn located in Norwich, Vermont—and is said to be the inspiration for the television series “Newhart.” Established in 1797, the inn consists of three separate buildings—the Main Inn, Ivy Lodge and Walker House—and offers 38 guest rooms with a range of amenities. The inn is also home to Jasper Murdock’s Alehouse, a pub and on-site brewery that produces award-winning, English-style ales from hops grown in the adjacent garden. Located about a mile from Hanover, New Hampshire, this Vermont getaway offers comfortable lodging for visitors while providing easy access to numerous area attractions and institutions.
Free WiFi Included

Vermont Bike Tour Traveler Photos

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Pre-Trip Extension - Norwich-Hanover

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