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Woodstock Self-Guided Bike Tour

  • Billings Farm cows at sunrise
  • Rt 12 Farm
  • Tunnel trail
  • Canoeing
  • Vermont with cattle
  • Red eft on hike in stream
  • Woodstock village from Mt. Tom
  • Silver Lake sunrise
  • Old River Rd in fall
DURATION
6 Day(s)
DAILY BIKING
21 to 38 miles
TRIP DIFFICULTY
2-Easier to Intermediate
STARTING FROM
$1795
SINGLES ADD FROM
$500

Trip Overview

Vermont is known for ample natural beauty … from mountains and forests to pristine river valleys and wildlife. On this trip, you are based in the picturesque village of Woodstock, located in central Vermont, in the shadow of the lovely Green Mountains. Enjoy this multisport adventure with the opportunity to experience and appreciate one of the most scenic parts of the state. You explore the area using a variety of modes — pedaling, hiking, and floating. Choose to participate in whichever activities appeal to you.

You unpack once and spend each evening at a single inn. Situated near the banks of the Ottauquechee River, your inn is a great launching point for each day's adventures. You are a short walk or ride from restaurants, shops, a National Historical Park and all the charm of Woodstock.

Itinerary

From start to finish, check out the route.

DAY 1 - Arrival Day: Bike Ottauquechee Valley
Distance: 21 miles | Terrain: Easier to Intermediate | The Shire
Meet at 11:30 a.m. at your inn and be ready to ride. After brief introductions and a bike fitting, you are on your way for your first adventure, a 21-mile pedal along the Ottauquechee River. Along your ride, pass four scenic bridges — the Middle Covered Bridge, the Taftsville Covered Bridge, the Quechee Covered Bridge, and the Quechee Gorge Bridge. Make sure your cameras are ready, because these bridges are a famous part of Vermont’s gorgeous scenery. Mid-ride, stop at Simon Pearce, a world-renowned creator of glassware and pottery. With their facilities perched atop the falls of the Ottauquechee River and overlooking a covered bridge, watch the glassblowers demonstrate their art. Consider taking home your very own piece of Simon Pearce glass as a memento from today’s ride ... and enjoy an up-scale lunch there if you reserve ahead. There are numerous other lunch opportunities along the route.

DAY 2 - Hike Mt. Tom
Distance: 4 miles | Terrain: Easier | The Shire
Today you switch to hiking mode to explore the Marsh-Billings-Rockefeller National Historical Park. After breakfast, pack a sandwich and set out for a walk along carriage roads and trails to the top of Mount Tom, which stands proud at 1,357 feet. Along the hike, see remnants of historic farming from days gone by. Observe the wide array of flora and fauna offered by diverse habitats. When you reach the peak, you can see the village of Woodstock, Mount Peg (Mount Tom’s sister peak), and the Ottauquechee River, which you biked along yesterday. After enjoying a tasty picnic lunch, explore the more historical side of the National Historic Park. Visit the Carriage Barn, which serves as the national park’s visitor center. Then tour the mansion that housed three conservationist families across nearly two centuries.
DAY 3 - Bike to Barnard
Distance: 21 or 35 miles | Terrain: Intermediate | The Shire
You’re back on your bike today. After breakfast, ride out of Woodstock through Prosper Valley to Barnard. You pass one of the trailheads for the Appalachian Trail, the iconic hiking trail that leads 2,200 miles from Georgia to Maine. Climb through scenic farms and descend to sparkling Silver Lake. Stop at the Barnard General Store for lunch, ice cream or snacks and enjoy the long descent back into Woodstock. If you wish to ride additional miles, pedal the ridge along North Road, with enticing views of the Green Mountains. Drop into the White River Valley, circle back to Barnard, and then head back to your inn.
DAY 4 - Float Connecticut River
Distance: 5 miles | Terrain: Easier | The Shire
Today starts with an optional early bike ride to South Woodstock of about 15 miles. Then get ready for a float on the lovely Connecticut River. You drive a half hour to nearby White River Junction, where you can grab lunch at British-inspired Piecemeal Pies or enjoy Turkish specialties at Tuckerbox Cafe. After lunch, head over to Windsor to choose your float method (canoe, kayak, raft, or stand-up paddleboard) and shuttle upriver to begin your three-hour float back to Windsor. When you return to Windsor, explore the Path of Life Sculpture Garden, located at the take-out. The garden includes 18 works of art displayed on 14 acres. Then head to Harpoon Brewery for a refreshing beverage. If you wish, you can tour the brewery.
DAY 5 - Hike Appalachian Trail
Distance: 4 to 12 miles | Terrain: Intermediate | The Shire
Pack a picnic today and enjoy quiet walking along ridges, across forested valleys through Barnard, Pomfret and Hartford. Look for deer tracks, birds, wildflowers and mountain views. You may cross paths with a long-hauler, someone traveling the entire 2,190 miles of the Appalachian Trail by foot — from Maine to Georgia. You have a few options for your hiking distances, hike more or return to your inn to relax.
DAY 6 - Bike Stage Road & Visit Billings Farm
Distance: 21 miles | Terrain: Easier
For your final adventure, take an early morning ride out of Woodstock to South Pomfret. Visit Teago, a newly renovated New England general store with loads of character. From there, continue the out-and-back through the bucolic countryside, again crossing the Appalachian Trail. Return back to the inn by 10 a.m. if you wish to take a post-ride shower.

Map

Dates & Pricing

Prices are per person based on double occupancy (2 people in one room). Single supplement for private room is listed at the top of this page. A deposit of $500 holds your reservation for most tours. For weekend tours, the deposit is $300.

Start End Cost Availability
Aug 07, 2022 Aug 12, 2022 $1795.00 Available! Reserve Reserve
Aug 21, 2022 Aug 26, 2022 $1795.00 Available! Reserve Reserve
Sep 11, 2022 Sep 16, 2022 $1795.00 Available! Reserve Reserve
Sep 25, 2022 Sep 30, 2022 $1795.00 Available! Reserve Reserve
Oct 02, 2022 Oct 07, 2022 $1795.00 Available! Reserve Reserve
Oct 16, 2022 Oct 21, 2022 $1795.00 Available! Reserve Reserve

What’s Included

5 nights’ lodging, bike and bike fitting, routes, hiking poles, kayaking/canoeing reservations.

Dates & Pricing

Prices are per person based on double occupancy (2 people in one room). Single supplement for private room is listed at the top of this page. A deposit of $500 holds your reservation for most tours. For weekend tours, the deposit is $300.

Start: Aug 07, 2022
End: Aug 12, 2022
Cost: $1795.00
Availability: Available!
Reserve
Start: Aug 21, 2022
End: Aug 26, 2022
Cost: $1795.00
Availability: Available!
Reserve
Start: Sep 11, 2022
End: Sep 16, 2022
Cost: $1795.00
Availability: Available!
Reserve
Start: Sep 25, 2022
End: Sep 30, 2022
Cost: $1795.00
Availability: Available!
Reserve
Start: Oct 02, 2022
End: Oct 07, 2022
Cost: $1795.00
Availability: Available!
Reserve
Start: Oct 16, 2022
End: Oct 21, 2022
Cost: $1795.00
Availability: Available!
Reserve

What’s Included

5 nights’ lodging, bike and bike fitting, routes, hiking poles, kayaking/canoeing reservations.

Inns

Where you stay along the way.

The Shire
Tucked away in the picturesque New England landscape, The Shire is a spacious getaway next to the river. Brimming with natural light, our airy property invites you to disconnect from the bustle and embrace nature. Explore the town, ski the nearby mountains, and come back to your own personal retreat at the end of the day.

Gallery

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

Billings Farm cows at sunrise Rt 12 Farm Tunnel trail Canoeing Vermont with cattle Red eft on hike in stream Woodstock village from Mt. Tom Silver Lake sunrise Old River Rd in fall