Vermont > Woodstock & Upper Valley Bike Tour – NEW!

2019 Dates: July 28-Aug. 2, Oct. 6-11, 2019 (this date sold out)

The Upper Valley region of Vermont and New Hampshire is a mecca for bicycling along three scenic rivers: the Connecticut, White and Ottauquechee. You’ll be thrilled with the vistas of farms, small towns and wooden bridges along the way. You’ll enjoy quiet roads, gorgeous countryside and delicious meals — featuring fresh, locally sourced ingredients.

This new tour connects some of the best area rides with stays at three fabulous historic inns. Ride by a spectacular plunging gorge, explore charming villages and attend a tasting of local craft beers. Bring home some farm-made maple products or a selection of local cheeses. You’ll fall in love with this picturesque region.

Vermont>Woodstock & Upper Valley Bike Tour Itinerary

DAY ONE  | Arrival Day | Distance 15 miles | Terrain: Easier | Hotel: Breakfast on the Connecticut
Meet in Lyme, New Hampshire, at our first inn, Breakfast on the Connecticut, at 2 p.m. on Sunday. Meet your leaders and other group members and take a short shakeout ride along the Connecticut River. You’ll get familiar with the slower pace and gorgeous views along the local back roads. Enjoy dinner together.

DAY TWO  |  Distance: 32 or 40 miles  |  Terrain: Easier | Hotel: Breakfast on the Connecticut 
The second day of riding features a loop up the Connecticut River Valley and back along lovely lakes and rivers on the Vermont side. Roll through farms and fields to Piermont, New Hampshire, where we cross the Connecticut and stop at the iconic Farm-Way store. Continue along Lake Morey and enjoy a picnic lunch. Cross back over the Connecticut River, with an optional loop around Lake Fairlee.

DAY THREE  |  Distance: 29 miles  |  Terrain: Easier to Intermediate |  Hotel: The Norwich Inn
Ride back into Vermont and out to Lake Fairlee, a beautiful rural lake dotted with cottages and camps. Listen for loons as you start cycling south along the lake, and see if you catch sight of glider planes landing nearby. A ride through historic Thetford Center brings you back toward Norwich, just across the Connecticut River from Hanover, New Hampshire — home of Dartmouth College.

DAY FOUR  |  Distance: 30 miles  |  Terrain: Easier to Intermediate | Hotel: The Woodstocker B&B
Leaving Norwich, you roll along the White River and then cross over the hills to the Quechee Gorge. Enjoy the breathtaking view of this channel and plunging falls forged into the rock by glaciers and the Ottauquechee River. Stop for lunch at the famous Simon Pearce restaurant. Don’t miss the glass blowing demonstration, and shop for fine glass in this historic mill building — powered by the action of the nearby river. From there, cycle past the Taftsville wooden covered bridge into the historic village of Woodstock.

DAY FIVE  |  Distance: 20 or 37 miles  |  Terrain: Intermediate | The Woodstocker B&B
Ride out of Woodstock through Prosper Valley up to Barnard. Cycle past the Billings Farm and Museum, and go over the Appalachian Trail (the iconic hiking trail that leads from Georgia to Maine). Then climb through scenic farms and descend to the shores of Silver Lake. Beyond Silver Lake, you ride the ridge out North Road, with views west to the peaks of the Green Mountains. The route drops into the White River valley and along the river and back to Barnard. Savor lunch at the Barnard General Store (circa 1834) and enjoy the vistas of Silver Lake before heading back on the long descent to Woodstock.

DAY SIX  |  Distance: 12 or 20 miles |  Terrain: Intermediate
Ride out of Woodstock to South Pomfret and visit another great New England general store (Teago). From there, there are two optional out-and-backs through the countryside and a gentle 5-mile ride back to the inn for showers and farewells.

Woodstock & Upper Valley, Vermont Bike Tour


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

July 28-Aug. 2, 2019: $2,295reserve
Reserve with $300 deposit

October 6-11, 2019: $2,295 (Sorry! Sold out)reserve
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: $650

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.


This peaceful New England getaway location features bright, airy rooms with a Shaker design. Enjoy the ambiance and ideal location overlooking the Connecticut River.


This historic Victorian inn was established in 1797. It welcomes you with cozy rooms and the full services you’d expect of a larger hotel. Relax on the classic front porch or stroll the hamlet of Norwich.


Enjoy this relaxing and romantic bed and breakfast in the heart of the historic village of Woodstock, Vermont. Each chic room is specially decorated with a unique theme, and each features the luxury of a king-sized bed and other amenities.


What’s Included

5 nights’ lodging, 4 dinners (one night on your own), 5 breakfasts, 3 lunches, beer tasting, bicycle and helmet, expert leaders, van support, detailed notes and directions.


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.