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Woodstock Weekend

  • Billings Farm cows sunrise
  • Woodstock barn
  • Bikers Old River Rd
  • Farm in Barnard
  • Fall colors Vermont
  • Jenne Farm biking
DURATION
4 Day(s)
DAILY BIKING
15 to 40 miles
TRIP DIFFICULTY
2-Easier to Intermediate
STARTING FROM
$1195
SINGLES FROM
$300

Trip Overview

Woodstock, Vermont, is known as one of the most scenic small towns in the U.S., and it has easy access to wonderful bike routes. Our 2020 four-day Woodstock Weekend Tours are designed around holiday weekends — allowing you to enjoy both the great biking and unique local celebrations full of New England charm and seasonal activities. On the Fourth of July weekend, for example, our inn’s back yard is just across the river from the local fireworks, enabling a relaxing celebration after a great day of riding. You stay at On The River Inn — a quiet spot just outside the bustle of downtown with a pool, sauna and more — and enjoy four of our favorite local rides. Plus, with two optional extended rides to the White River Valley, there is plenty to challenge enthusiastic riders. More casual riders can stick to the river valleys or use an e-bike to joyfully ride alongside the most energetic riders. Your dinners are at two distinguished local establishments and one night at On the River Inn’s fine restaurant.

Itinerary

From start to finish, check out the route.

DAY 1 - Arrival Day
Distance: 12 to 20 miles | Terrain: Easier to Intermediate | 506 On The River Inn
For those who arrive in the early afternoon, you can explore town and then meet your group at 3 p.m. for a short shakeout ride. Cycle through the Marsh-Billings-Rockefeller National Historical Park and along the valley to South Pomfret. Passing the Suicide Six ski area, you will head up a quiet stretch of Stage Road, crossing the Appalachian Trail. At the end of the pavement, you turn around and return slightly downhill all the way to Woodstock. Tonight’s welcome dinner is at Max’s Tavern in the Barnard Inn.
DAY 2 - Silver Lake
Distance: 20 or 28 miles | Terrain: Intermediate | Hotel: On The River Inn
Ride out of Woodstock through Prosper Valley to Barnard. Cycle past the Billings Farm and Museum and over the Appalachian Trail ( the iconic hiking trail that leads from George to Maine). Then climb through scenic farms and descend to Silver Lake. Ride the ridge out North Road, with views of the Green Mountains. Drop into the White River Valley and back to Barnard. Have lunch at the Barnard General store and head back on the long descent to Woodstock. Dinner at On the River Inn.
DAY 3 - Covered bridges ride
Distance: 24 or 38 miles| Terrain: Easier to Intermediate | On The River Inn
Take the iconic “covered bridges ride,” with an optional route to Pomfret and the beautiful farm roads down to the White River and on to Quechee. Or enjoy an easier ride along the Ottaquechee River to Quechee Gorge State Park. Don’t miss the glass blowing demonstration at Simon Pearce Glass, and shop for fine glass in this historic mill building — powered by the action of the nearby river. Lunch is on your own today and the Quechee Gorge has great options! From there, cycle past the Taftsville wooden covered bridge into the historic village of Woodstock. Enjoy a final celebratory dinner together in Woodstock.
DAY 4 - Departure Day
Distance: 20 miles | Terrain: Easier to Intermediate
Cycle through South Woodstock’s lovely horse country — stopping for a quick coffee at the South Woodstock Country Store. Continue up the valley in Reading and take a short side trip to the famously scenic Jenne Farm. This gorgeous vista is a famous backdrop for everything from Budweiser Clydesdale commercials to Forrest Gump. It provides a great turn around for today’s ride, followed by a down river trip back into Woodstock. You return to On the River Inn for showers and a final farewell.

Map

Woodstock Road Weekend map

Dates & Pricing

Make your reservation with confidence. Your tour is completely 100% refundable until the final payment due date.

Start End Cost Availability
May 22, 2020 May 25, 2020 $1195.00 Available! Reserve Reserve
Jun 19, 2020 Jun 22, 2020 $1195.00 Available! Reserve Reserve
Jul 03, 2020 Jul 06, 2020 $1195.00 Available! Reserve Reserve

What’s Included

3 nights of lodging; 3 breakfasts and 3 dinners; free use of bicycle and helmet; detailed maps and itineraries; experienced guides; full van support; cycling at your own pace along routes that we have carefully selected and continually improve. Airfare is not included

Dates & Pricing

Make your reservation with confidence. Your tour is completely 100% refundable until the final payment due date.

Start: May 22, 2020
End: May 25, 2020
Cost: $1195.00
Availability: Available!
Reserve
Start: Jun 19, 2020
End: Jun 22, 2020
Cost: $1195.00
Availability: Available!
Reserve
Start: Jul 03, 2020
End: Jul 06, 2020
Cost: $1195.00
Availability: Available!
Reserve

What’s Included

3 nights of lodging; 3 breakfasts and 3 dinners; free use of bicycle and helmet; detailed maps and itineraries; experienced guides; full van support; cycling at your own pace along routes that we have carefully selected and continually improve. Airfare is not included

Inns

Where you stay along the way.

506 On The River Inn
On the River Inn is pure Vermont! Experience the best of Woodstock. Stay in super comfy rooms with beautiful views. Have a country breakfast in their farmhouse kitchen. Enjoy all day complimentary coffee, tea and cookies, indoor pool & sauna.

Gallery

Images from this tour. Click each to see it larger.

Billings Farm cows sunrise Woodstock barn Bikers Old River Rd Farm in Barnard Fall colors Vermont Jenne Farm biking