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Biking Southern Vermont: A New England Idyll

National ParksScenic 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 Activity
  • Ideal for energetic beginners to more experienced riders.

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

  • Delight in 5 nights at charming, historic Vermont inns
  • Learn how maple sugar is made at a genuine “sugar house”
  • Browse the old-fashioned penny candy at the Vermont Country Store
  • Meet a local to hear about the thriving cheese-making movement
  • Admire the hewn-granite homes of North Chester’s Stone Village
  • Gather for a delicious picnic lunch at Rockledge Farm
  • Meet local artisans and see how they work Vermont hardwoods
  • Visit the Calvin Coolidge Homestead in Plymouth Notch
  • Tour the Long Trail Brewing Company, with lunch
  • Cycle the serene back roads of Woodstock and Quechee Village
  • Watch talented glassblowers at work in their studio
  • Hike from Woodstock through Billings Park to Mount Tom

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 High/Low Temperature (°F) – Woodstock
May  68º/42º  Jun  77º/52º  Jul  81º/57º  Aug  79º/55º  Sep 72º/46º  Oct 58º/34º

Average Precipitation (in.) – Woodstock
May 4  Jun 3.5  Jul 4  Aug 3.5   Sep  3.5  Oct 3.5

What’s Included:

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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. 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
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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 your tour, and back to Hanover at the conclusion of the tour. Your transfer leaves from the bus stop located between The Hanover Inn and The Hopkins Center on Wheelock Street in Hanover, New Hampshire, at approximately 1:15 p.m. Please look for a representative holding a VBT sign. The shuttle will be coming from your 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.

Hanover is served by Dartmouth Coach ( from both Boston’s South Station and Boston Logan Airport. There is currently a departure from Logan Airport at 8:55 am and from Boston’s South Station at 9:30 am that arrives in Hanover, NH at 12:00 noon. Greyhound ( provides transport from Boston’s South Station. There is currently a 10:30 am departure from Boston’s South Station that makes at stop at the airport in Manchester, NH and arrives in Hanover, NH at 1:00 pm. The Hanover terminals for both lines are within a block of the Hanover Inn and our shuttle collection point.

Hanover is also close to the Lebanon Municipal Airport (LEB), which is served by Cape Air from Boston, and to Amtrak’s White River Junction station. Note that taxi service from LEB is limited and booking in advance is recommended. Taxi contact information is available at

VBT Pre-Trip Extension guests: You have another morning to enjoy Norwich at leisure. At 1:00 p.m., 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 p.m., 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 your 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, you’ll begin biking south and then east, crossing your 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 you’ll discover how maple syrup is made; Vermont is the nation’s largest producer. Though the sap won’t be running during the cycling season, your visit here is sure to be illuminating, and you’ll also be able to purchase a tasty souvenir. You’ll arrive in Chester in time for lunch.

Back in Grafton, there is time for a refreshing dip in the nearby swimming hole before you meet with a friendly, in-the-know local to hear all about cheese production in Vermont and the Windham Foundation, a nonprofit 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 your route, you’ll ride over the Springfield Dam. Stop to enjoy a picnic lunch, prepared by your Trip Leaders, at the delightful Rockledge Farm. You’ll have the opportunity here to meet the local artisans and see how Vermont hardwoods are crafted into stunning utensils, serving boards, and furniture. Afterwards, continue cycling towards your inn, The Inn at Water’s Edge. Take a seat in a rocker and enjoy the inn’s location overlooking quiet Echo Lake.

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

This afternoon, you’ll visit the Long Trail Brewing Company and enjoy lunch and you may decide to have a sampling of this fine brewery’s award-winning craft beers. Then ride along a quiet back road into Woodstock.

Ladies’ Home Journal named Woodstock “The Prettiest Small Town in America”—and you’ll discover why it’s so special during your two-night stay at 506 On the River.

After a day of biking, you may choose to visit the inn’s indoor pool and sauna this evening or relax on the six acres of peaceful grounds. Later, your Trip Leaders can offer recommendations about which restaurants to try for a dinner on your own.

Hotel: 506 On the River
Meals: B, L
Daily Options: 22 or 28 miles

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

Today you’ll 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, admission to which is included in the cost of your trip. You’ll 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 it 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.

Hotel: 506 On the River
Meals: B, D
Daily Options: 20 or 32 miles

DAY 6: Mount Tom walk / Depart for home

This morning, you’ll cross your last covered bridge of the week—on foot, this time, as you embark on a walk from Woodstock. Your 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! 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.

Your tour concludes back at 506 On the River. Checkout time is 11:00 a.m. 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 506 On the River at 1:00 p.m. 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 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 an 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 a member of Historic Hotels of America, Distinctive Inns of New England, the Vermont Fresh Network, and Green Hotels of Vermont.
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

506 On the River

506 On the River was built in 2014 and offers stylish rooms with vintage-chic décor and river views. Amenities include a bistro, bar, lounge, gift shop, library, indoor pool, and sauna. Just two miles from the village of Woodstock, the inn is a perfect place to unwind.
Free WiFi Included

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Pre-Trip Extension - Norwich, VT-Hanover, NH

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