6-Day Self-Guided Woodstock New England Bike Tour

Please meet at The Shire at 11:30am, 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.
Accommodation: The Shire
Meals: No meals

Biking: 21 miles (33 kilometres)
Terrain: Easier to Intermediate

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.
Accommodation: The Shire
Meals: No meals

Biking: 4 miles (6.4 kilometres)
Terrain: Easier

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.
Accommodation: The Shire
Meals: No meals

Biking: 21 or 35 miles (33 or 56 kilometres)
Terrain: Intermediate

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.
Accommodation: The Shire
Meals: No meals

Biking: 5 miles (8 kilometres)
Terrain: Easier

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.
Accommodation: The Shire
Meals: No meals

Biking: 4 to 12 miles (6.4 to 19 kilometres)
Terrain: Intermediate

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.
Accommodation: Not applicable
Meals: No meals

Biking: 21 miles (34 kilometres)
Terrain: Easier