Vermont > Northeast Kingdom Bike Tour

Aug. 4-9, 2019

Stowe, Canada, Caspian Lake, Greensboro and Vermont’s famous Northeast Kingdom…this tour has it all! We begin near the sophisticated village of Stowe and then cycle through Smuggler’s Notch into the meandering Lamoille River Valley. We then explore Vermont’s Northeast Kingdom, the least settled and most rural, untouched corner of the state. We parallel the Missisquoi River as we cycle part of a rail trail, and enjoy a wonderful mix of sunny farmland, shaded forest and quiet wetlands. We bike through international customs as we wend our way into Canada (must bring your passport!). Here we have lunch in the historic village of Frelighsbugh and then pass along the foothills of Mount Pinnacle, through beautiful apple orchards and farms, and then back into the United States.

We also include visits to some quintessential Vermont villages such as Montgomery, Greensboro, and Irasburg; stop at some wonderful old-fashioned stores; have a beautiful, optional ride to lake Willoughby; and include a tour of the Cabot Creamery, “makers of the best cheddar in the world”.

All this superb cycling is enjoyed while staying at three lovely inns. The Green Mountain Inn has a warm, country feel and the Phineas Swann Inn in Montgomery is a fully restored romantic inn that recently earned acclaim as Vermonts B&B of the year. We also stay two nights at the Highland Lodge, a family-owned country inn nestled in the heart of the Northeast Kingdom and overlooking Caspian Lake.

You will surely find that the somewhat longer and more energetic days on this tour are delightful, and well worth the effort. Or, join us for our ALL e-bike tour on Sept. 29-Oct. 4, 2019, when the entire group can have an electric assist up those hills.

Vermont Northeast Kingdom, Vermont Biking Tour Itinerary

DAY ONE  | Arrival Day | Green Mountain Inn
Sunday is Arrival Day. Settle in at the Green Mountain Inn located in the beautiful village of Stowe. This immensely popular inn treats us to a perfect blend of country ambiance and the modern comforts of an exceptional resort, and the beautiful village of Stowe provides an incredible array of sophisticated shops and galleries.

DAY TWO  |  Distance: 49 or 62 miles  |  Terrain: Intermediate to Advanced | Phineas Swann Inn
Start with a pleasant downhill ride and then rolling terrain past the entrance to Stowe (“ski capital of the East!”). Mt. Mansfield towers over this valley as we ride or shuttle through the mile-long twisting climb to Smuggler’s Notch. This is a challenging short stretch that many enjoy riding and many opt to take up our offer to use the van. We then drop down into the Lamoille River Valley and pass through the quaint village of Jeffersonville. Heading north we begin our exploration of Vermont’s Northeast Kingdom, the least settled and most rural, untouched corner of our state.

Following scenic rolling terrain we enjoy wonderful views of Spruce Peak and Jay Peak as we ride through Bakersfield and picturesque Sheldon. Our last few miles are particularly beautiful with large old farms and covered bridges marking our way to Montgomery Center and the Phineas Swann Inn. An optional ride takes us through Franklin and along the shores of Lake Carmi, adding 13 miles to the day.

The Phineas Swann offers us luxurious accommodations furnished with fine antiques and romantic four-poster beds. The inn was voted Readers’ Choice for Best of New England 2010 by Yankee Magazine; was rated as one of the Top 5 Most Romantic Inns in New England by Boston Magazine, and the Innkeepers were named Innkeepers of the year for Vermont in 2009.

DAY THREE  |  Distance: 30, 41 or 61 miles  |  Terrain: Intermediate to Advanced | Phineas Swann Inn
Today we cycle through some of Vermont’s prettiest farm country passing some of Montgomery’s famous covered bridges before crossing the border into French-speaking Canada (be sure to bring your passport!). We can have an excellent lunch in pretty Frelighsburg and the optional ride through Pigeon Hill includes a visit to Stanbridge East with its famous mill and waterwheel, and the Musee Missisquoi. Our ride back into the U.S. takes us past apple orchards and to the Domaine Pinnacle where we can enjoy their tasting room that includes all of their renowned Ice Apple Wine products and local gourmet food specialties.

DAY FOUR  |  Distance: 59 or 73 miles  |  Terrain: Intermediate to Advanced | Highland Lodge
Today is a long ride as we cycle into the heart of the Northeast Kingdom, passing bogs often frequented by moose and deer, enjoying great views of Camel’s Hump, the Worcester Mountains and Jay Peak, and riding over and down Irasburg Hill where we often picnic at the gazebo on the green. Easy rolling terrain is welcome as we ride south to Craftsbury and then we climb back to Greensboro and the Highland Lodge. Today we also have a spectacular optional ride leading from Irasburg to Orleans and then to beautiful Lake Willoughby. The option then loops back through Barton passing Crystal Lake and Caspian Lake before arriving at the inn. We stay the next two nights at the Highland Lodge, a supremely welcoming and relaxing family-owned inn overlooking the shores of beautiful Caspian Lake.

DAY FIVE  |  Distance: 32, 42 or 51 miles  |  Terrain: Intermediate | Highland Lodge
Today’s ride starts with an optional visit to Willey’s, a quintessential Vermont Country Store. Then we ride steeply downhill to Greensboro Bend before a climb to the intersection with Route 215 in Walden that takes us on a beautiful downhill section into Cabot. Here we can enjoy a tour of the Cabot Cheese factory “makers of the best cheddar in the world.” You can turn here for Greensboro or take a beautiful rolling ride to Marshfield where we can delight in the confections at Rainbow Sweets and perhaps picnic by the waterfalls. We reverse our route to East Hardwick and then follow remnants of the historical Bailey-Hazen Road before descending past beautiful Caspian Lake before arriving back at the Highland Lodge. An optional 14 mile ride takes us to West Danville and Joe’s Pond and then past Molly’s Falls Pond before arriving back on the Standard Route in Marshfield.

DAY SIX  |  Distance: 36 miles  |  Terrain: Intermediate
Today we take a roller coaster ride down to the village of Hardwick and then begin to parallel the Lamoille River, stopping to visit the Fisher Covered Bridge (one of the last remaining covered bridges built specifically for railroads). We follow a scenic route through Wolcott and then into Morrisville. From here we take a rural route along Randolph Road back to the Green Mountain Inn Stowe.

Northeast Kingdom, Vermont Bike Tour


Make your reservation with confidence. Your tour is completely 100% refundable up to 60 days of the tour date.


August 4-9, 2019: $1995 
Reserve with $300 deposit

Final payment due 60 days prior to your tour (personal check, Visa, MasterCard, American Express or Discover)

Single Supplement Fee for Private Room: $310

Cancellations: If you cancel your tour reservation, your cancellation fee will be determined as follows:

  • If you cancel 60 or more days prior to the start of your tour, there is no cancellation fee.
  • If you cancel between 45 and 59 days prior to the start of your tour, you will forfeit 50% of all tour payments.
  • If you cancel between 0 and 44 days prior to the start of your tour, all tour payments will be forfeited.



For more than 180 years, the Green Mountain Inn has captivated travelers from around the world. Located on Main Street in the heart of historic Stowe, our rich history and overwhelming beauty entices our visitors to return. With the perfect blend of classic ambience and modern comfort in our 104 accommodations housed in 8 separate buildings, we offer a variety of activities including our recently renovated year-round outdoor pool and spa, health club, game room, fire pit, and afternoon tea & cookies.

logo-phineas-swann-innLooking for a romantic getaway in Vermont? Look no further than the Phineas Swann Bed and Breakfast Inn. Boston Magazine has named Phineas Swann Bed and Breakfast Inn one of New England’s Top 5 Romantic Inns in their Best Winter Escapes magazine.

The Highland Lodge is a family-owned country inn nestled in the heart of the Northeast Kingdom, overlooking crystal clear Caspian Lake in Greensboro, Vermont.

What’s Included

A tour of the home of Cabot Cheese, 5 nights lodging, 5 breakfasts, 5 dinners, bicycle and helmet. Free transfer provided from/to Burlington International Airport.


We are happy to provide you with a bike to use at no charge. Our bikes come equipped with a front handlebar bag, rear carrier, water bottle, mirror and flat pedals. Pedal cages and soft gel seat covers are available on request. We are also happy to put your own clipless pedals (pedals that attach to your biking shoes) and seat on your bike if you wish. Specific details and styles of bikes available in each location are indicated under each photograph below. The make of bikes provided varies by location.

A collection of photos from a variety of our Vermont tours.