Stowe to Woodstock

Vermont has long been celebrated for its beautiful, rural nature with postcard pretty villages among the river valleys, verdant forests and abundance of historic covered bridges. Maple sugar shacks, and old barns stand testament to multi-generational farms that keep locals attached to the land. From Stowe, with its ski-town vibe to historic Waitsfield and charming Woodstock, nestled in a valley so beautiful it has been named one of the America’s prettiest towns by both National Geographic and the American Architectural Society, you’ll experience the best cycling in the state, while staying in exceptional inns and lodges.

We offer two other itineraries in Vermont:



Stowe, VT, USA

Day 1+2


Morrisville, Morristown, VT, USA

Day 2


Montpelier, VT, USA

Day 3


Waitsfield, VT, USA

Day 4


Woodstock, VT, USA

Day 5+6+7

What’s Included in the Cost of Your Trip?


6 nights lodging
All breakfasts and 1 dinner
Luggage transfers
Detailed GPS instructions & maps
Personal meet & greet with our local Area Manager
Area Manager available throughout the tour



You can start any date between May and October.
In the fall, when the mountains turn red and gold – the views are spectacular.


7 days / 6 nights


Stowe / Woodstock






Classic Accommodation: US $2,450 pp
Single supplement: US $600

Luxe Accommodation: US $3,050 pp
Single supplement: US $775

Bike Rentals

Hybrid or Racing Bikes: US$280

E-Bikes: US$480*

*E-bikes are generally available but are on an ‘on request basis ‘ and will be confirmed on receipt of your booking registration. Rental rates include delivery to the first hotel and pick-up from the last hotel. E-bikes provided are the best rentals available in the region. If having an e-bike will make your trip, we’ll do our best to provide. E-bike rentals are non-refundable. 

Please note: Final itinerary is subject to revision; any changes made are done so in an attempt to provide the best possible trip given route conditions and available services. Due to the nature of our business and exchange rates, prices are subject to change. All prices quoted are U.S. dollars but we gladly accept payment in Canadian dollars also. If you have any questions before making your reservation, please contact us.
Getting There Stowe is just a 45 minute drive from Burlington International Airport (BTV). Direct flights from major cities include Atlanta, Charlotte, Chicago, Newark, New York (JFK and LGA) Orlando, Philadelphia, Toronto and Washington DC. Taxis from Burlington to Stowe cost approximately $70 with Burlington Taxi.


Day 1


Arrive at your leisure to Stowe, the idyllic Vermont ski town, now as popular in spring, summer & fall, for among other attractions, great cycling. Early afternoon (you can check in from 2pm), meet your bikes and take a warm-up ride out to the Von Trapp lodge outside of Stowe, where the family purchased a farm in a spectacular setting that reminded them of Austria. Stop in at the Alchemist, a craft brewery where you can tour and taste. Back in town, stroll up Main Street, a quaint strip of independent shops (no chain stores here), bookended by a white steeple church and a covered walking bridge. Stay at charming Green Mountain Inn, which was built in 1833.

Ride distance: 12mi (20km); elevation gain 1,000’ (340m).


Day 2

Stowe & Morrisville

We have several options for you to consider today; the main route leads to the historic town of Morrisville, with add-on options including a loop around Lake Lamoille. Stop by an antique store on the return route and admire New England collectibles. Back in Stowe, enjoy a massage or explore more of the town; adventure seekers might consider a zip line tour from the mountain top.

Ride distance: 20mi (32km); elevation gain 1,175’ (390m) or 24mi (39km); gain 1,410’ (470m) or 32mi (52km); gain 1,860’ (620m).


Day 3

Montpelier & Mad River Valley

Ride south from Stowe along the Putnam State Forest to Waterbury; stop by Waterbury State Park and gaze onto the reservoir here. Pop into a glassblowing studio or a cider mill or head straight for Ben & Jerry’s, the Vermont celebrated ice-cream makers. There is an add-on ride option to the charming village of Montpelier located on the Winooski River. Following the Mad River Valley on freshly paved road, stop at an organic farm that you can tour and taste at, including their maple syrup. In Waitsfield admire a covered bridge that has been here since 1833 (it may be the oldest in Vermont).

Ride distance: 31mi (50km); elevation gain 2,190’ (730m) or 43mi (70km); gain 2,880’ (960m).


Day 4

Waitsfield & Warren

Choose between a short loop near Sugarbush (hiking is also an option) or an intermediate ride to Middlesex, Waterbury and back through Warren. Lunch options abound in each. In case you are interested in soaring in a glider, you can do this nearby. On a clear day, you’ll see the Adirondacks and Lake Champlain to the west, Camel’s Hump and Mt. Mansfield to the north, and Mt. Washington and the White Mountains to the east.

Ride distance: 21mi (35km); elevation gain 1,860’ (620m) or 43mi (70km); gain 2,880’ (960m).


Day 5


Ride from Waitsfield south along the Mad River. Stop and view scenic Warren Falls and then further south, pop into a glass blowing studio & gallery. The Rochester Café & Country Store is an option for lunch, or continue further to Barnard General Store which boasts a nice picnic spot overlooking Silver Lake. Enjoy a swim at the sandy beach here. Close to Woodstock you can visit the Billings Farm & Museum, which shows visitors what farm life was like in the 1890s. The working dairy farm allows you to see cows being milked, sheep being sheared and horses plowing. Arrive to Woodstock and marvel at the covered bridge over the Ottauquechee River. Stay at the charming and luxurious Woodstock Inn & Resort. Enjoy the spa and then tuck into a great meal at dinner time.

Ride distance: 32mi (52km); elevation gain 1,440’ (480m) with shuttle or 62mi (100km); gain 2,490’ (830m).


Day 6

Woodstock & Quechee

Today, follow the Ottauquechee River to Taftsville and Quechee. You’ll have the chance to see 4 covered bridges today – Quechee’s is 70 feet long and one of the most photographed in Vermont. Stop at Simon Pearce for a glassblowing demonstration and at the Quechee gorge, marvel at the views. Back in Woodstock, opt for an afternoon hike on Mt. Tam with views of Woodstock, Mount Peg and the river valley you biked in the morning. Visit the Carriage Barn, which serves as the national park’s visitor center and then tour the Marsh-Billings-Rockefeller mansion. Longer cycling options visit other villages west of Woodstock towards Killington. Enjoy dinner in the fine dining room of the Woodstock Inn.

Ride distance: 17mi (28km); elevation gain 864’ (288m) or 34mi (55km); gain 1,440’ (480m) or 43mi (70km); gain 2,820’ (940m).


Day 7

Departure Day

Depart at your leisure.


Brass Lantern Inn, Stowe

The Brass Lantern Inn began as a modest farmhouse with separate carriage house and expansive farm. The original brick house and wood framed carriage house is ca. 1810. With 12 guest rooms, the property sits on 1.5 acre with views of Mount Mansfield. Less than 1 mile from the historic center of Stowe.

Waitsfield Inn, Waitsfield

Dating from 1825, this traditional inn is 1 mile from Waitsfield historic village and has just 12 rooms, many with antiques. There’s a living room with fireplace, library bar and dining room for guests.

The Shire, Woodstock

Overlooking the Ottauquechee River, this relaxed hotel features bright rooms with traditional New England decor, most with river views. There is a furnished wraparound porch as well as riverside seating.


Green Mountain Inn, Stowe

Located in historic downtown, this elegant hotel dates from 1833, with a dining room, casual bar/grill, fitness center and heated outdoor pool. Just outside their door is vibrant Main Street with its many unique shops, restaurants, historic gems, a 5.5 mile recreation path.

The Pitcher Inn, Warren

Nestled in the charming village of Warren, in the Mad River Valley, this Relais & Chateaux property offers well-appointed suites and guest rooms, exceptional fine dining and attentive staff. Amenities include an indoor and outdoor pool, sauna and three covered and six outdoor tennis courts.
*itinerary uses either the Pitcher Inn or the Inn at Round Barn which are comparable.

The Inn at the Round Barn Farm, Waitsfield

Set in a 19th century farmhouse and adjacent barn on 245 acres of countryside, this property boasts country-chic rooms with canopy beds, salons and an indoor pool and spa. The grounds include ponds, gardens and hiking trails.
*itinerary uses either the Pitcher Inn or the Inn at Round Barn which are comparable.

Woodstock Inn, Woodstock

This venerable inn is divine with comfortable guest rooms, three restaurants, tennis courts, fitness center, indoor and outdoor pools, and spa. There has been an inn at this location since 1793 (the town was founded in 1765). The upscale property is now owned by the Woodstock Foundation, established by Laurance and Mary Rockefeller in 1968 to protect Woodstock’s natural beauty.

Trip starting at
USD $2,450