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Woodstock Multisport Bike Tour

  • Biking with view of ridges
  • Rt 12 farm
  • Canoe with two
  • Hiking in green tunnel
  • Red eft on hike
  • Biking near cattle
  • Woodstock from Mount Tom
  • Billings Farm in Woodstock
  • Silver Lake sunrise
DURATION
6 Day(s)
DAILY BIKING
21 to 38 miles
TRIP DIFFICULTY
2-Easier to Intermediate
STARTING FROM
$1795
SINGLES ADD FROM
$450

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 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 spend each evening at a well-located inn called The Shire. Situated on the banks of the Ottauquechee River, this is the ideal hub from which to explore the area. In between your multisport adventures, retreat to the large wraparound porch to sit in a rocking chair — with a cup of coffee or tea in hand — and take in the peaceful panoramic views. Across the river, notice cattle grazing at Billings Farm, which you can visit during the tour.

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, The Shire, 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. There are numerous lunch opportunities along the route.

Tonight you dine with the group at Worthy Kitchen. This counter-serve restaurant is a unique experience, known for its farm-to-table American eats.
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 enjoying breakfast on your own, meet mid-morning 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. Dinner is on your own.
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 The Shire. You’re on your own again for dinner tonight.
DAY 4 - Float Connecticut River
Distance: 5 miles | Terrain: Easier | The Shire
Today’s exploration is a float on the lovely Connecticut River. You shuttle a half hour to nearby Windsor, where you can grab a lunch at Artisan Eats. After lunch, walk next door, 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, compliments of Discovery. If you wish, you can tour the brewery. Afterward, you shuttle back to The Shire. You’re on your own for dinner tonight.
DAY 5 - Hike Appalachian Trail
Distance: 4 to 12 miles | Terrain: Intermediate | The Shire
Today you don your hiking boots once again. Meet at 10 a.m., pick up your box lunch and hop in the van for a short shuttle to the trailhead. 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 distance and can be picked up by the van at a couple of points and return to The Shire to relax ... or for more explorations of the village of Woodstock. For our final dinner tonight, Discovery treats you to a celebration at a Woodstock eatery.
DAY 6 - Bike Stage Road & Visit Billings Farm
Distance: 21 miles | Terrain: Easier | The Shire
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. After check-out, at 11 a.m., shuttle to Billings Farm & Museum. Known as one of the best outdoor history museums, this New England demonstration farm makes education entertaining. Then say farewell to the dairy cows and to your cycling friends … as you shuttle back to The Shire for departure.

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, The Shire, 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. There are numerous lunch opportunities along the route.
Tonight you dine with the group at Worthy Kitchen. This counter-serve restaurant is a unique experience, known for its farm-to-table American eats.
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 enjoying breakfast on your own, meet mid-morning 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 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, stop for an ice cream at the Creek House Diner, circle back to Barnard, and then head back to The Shire. You’re on your own again for dinner tonight.
DAY 4 - Float Connecticut River
Distance: 5 miles | Terrain: Easier | The Shire
Today’s exploration is a float on the lovely Connecticut River. You shuttle a half hour to nearby Windsor, where you can grab a lunch at Artisan Eats. After lunch, walk next door, 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, compliments of Discovery. If you wish, you can tour the brewery. Afterward, you shuttle back to The Shire. You’re on your own for dinner tonight.
DAY 5 - Hike Appalachian Trail
Distance: 4 to 12 miles | Terrain: Intermediate | The Shire
Today you don your hiking boots once again. Meet at 10 a.m., pick up your box lunch and hop in the van for a short shuttle to the trailhead. 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 distance and can be picked up by the van at a couple of points and return to The Shire to relax ... or for more explorations of the village of Woodstock. For our final dinner tonight, Discovery treats you to a celebration at a Woodstock eatery.
DAY 6 - Bike Stage Road & Visit Billings Farm
Distance: 21 miles | Terrain: Easier | The Shire
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. After check-out, at 11 a.m., shuttle to Billings Farm & Museum. Known as one of the best outdoor history museums, this New England demonstration farm makes education entertaining. Then say farewell to the dairy cows and to your cycling friends … as you shuttle back to The Shire for departure.

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, The Shire, 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. There are numerous lunch opportunities along the route.
Tonight you dine with the group at Worthy Kitchen. This counter-serve restaurant is a unique experience, known for its farm-to-table American eats.
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 enjoying breakfast on your own, meet mid-morning 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 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, stop for an ice cream at the Creek House Diner, circle back to Barnard, and then head back to The Shire. You’re on your own again for dinner tonight.
DAY 4 - Float Connecticut River
Distance: 5 miles | Terrain: Easier | The Shire
Today’s exploration is a float on the lovely Connecticut River. You shuttle a half hour to nearby Windsor, where you can grab a lunch at Artisan Eats. After lunch, walk next door, 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, compliments of Discovery. If you wish, you can tour the brewery. Afterward, you shuttle back to The Shire. You’re on your own for dinner tonight.
DAY 5 - Hike Appalachian Trail
Distance: 4 to 12 miles | Terrain: Intermediate | The Shire
Today you don your hiking boots once again. Meet at 10 a.m., pick up your box lunch and hop in the van for a short shuttle to the trailhead. 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 distance and can be picked up by the van at a couple of points and return to The Shire to relax ... or for more explorations of the village of Woodstock. For our final dinner tonight, Discovery treats you to a celebration at a Woodstock eatery.
DAY 6 - Bike Stage Road & Visit Billings Farm
Distance: 21 miles | Terrain: Easier | The Shire
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. After check-out, at 11 a.m., shuttle to Billings Farm & Museum. Known as one of the best outdoor history museums, this New England demonstration farm makes education entertaining. Then say farewell to the dairy cows and to your cycling friends … as you shuttle back to The Shire for departure.

Map

Dates & Pricing

Prices are based on double occupancy. 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 22, 2021 Aug 27, 2021 $1795.00 1 to 4 spaces left! Reserve Reserve
Sep 26, 2021 Oct 01, 2021 $1795.00 Date SOLD OUT Sold Out Sold Out
Oct 10, 2021 Oct 15, 2021 $1795.00 Available! Reserve Reserve

What’s Included

Professionally guided biking, hiking, and kayaking/canoeing, 5 nights’ lodging, 2 box lunches, and 2 dinners (you are on your own for all 5 breakfasts, 3 lunches, and 3 dinners — all available within walking distance of the inn), prepackaged snacks to take along on your adventures, two leaders, van support, bicycle and helmet, kayaks/canoes, admission to Marsh-Billings-Rockefeller National Historical Park and Billings Farm.

Dates & Pricing

Prices are based on double occupancy. 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 22, 2021
End: Aug 27, 2021
Cost: $1795.00
Availability: 1 to 4 spaces left!
Reserve
Start: Sep 26, 2021
End: Oct 01, 2021
Cost: $1795.00
Availability: Date SOLD OUT
Sold Out
Start: Oct 10, 2021
End: Oct 15, 2021
Cost: $1795.00
Availability: Available!
Reserve

What’s Included

Professionally guided biking, hiking, and kayaking/canoeing, 5 nights’ lodging, 2 box lunches, and 2 dinners (you are on your own for all 5 breakfasts, 3 lunches, and 3 dinners — all available within walking distance of the inn), prepackaged snacks to take along on your adventures, two leaders, van support, bicycle and helmet, kayaks/canoes, admission to Marsh-Billings-Rockefeller National Historical Park and Billings Farm.

Inns

Where you stay along the way.

The Shire Woodstock
Set on the banks of the Ottauquechee River in the picturesque Village of Woodstock, Vermont, The Shire Woodstock offers a rare respite from today’s hectic world. Explore the pastoral countryside, walk the charming downtown, or laze the day away in a rocking chair and enjoy our panoramic river views.

Inns

Where you stay along the way.

The Shire Woodstock
Set on the banks of the Ottauquechee River in the picturesque Village of Woodstock, Vermont, The Shire Woodstock offers a rare respite from today’s hectic world. Explore the pastoral countryside, walk the charming downtown, or laze the day away in a rocking chair and enjoy our panoramic river views.

Inns

Where you stay along the way.

The Shire Woodstock
Set on the banks of the Ottauquechee River in the picturesque Village of Woodstock, Vermont, The Shire Woodstock offers a rare respite from today’s hectic world. Explore the pastoral countryside, walk the charming downtown, or laze the day away in a rocking chair and enjoy our panoramic river views.

Gallery

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

Biking with view of ridges Rt 12 farm Canoe with two Hiking in green tunnel Red eft on hike Biking near cattle Woodstock from Mount Tom Billings Farm in Woodstock Silver Lake sunrise