Outdoor Experiences

Hit the outdoors for an unforgettable experience led by expert local guides! Take advantage of our concierge service to arrange your whole stay for you. Here are a few favorites – call or email if you have questions.

Winter outdoor activities

  • Saskadena Six (a 10-minute drive from the B&B), is a smaller and sweet resort with a nice mix of beginner, intermediate, and advanced trails, a super cozy lodge complete with massive fireplace, bar, food, rentals, and shop.
  • Killington, aka The Beast of the East, is the Northeast’s largest ski resort and is open for skiing and riding from late Fall to the Spring. In 2019, Killington will be once again hosting the Women's World Cup over Thanksgiving weekend. Its Skyeship gondola is only 20 minutes from The Woodstocker B&B, while the base lodge is a 30-minute drive.
  • Pico Mountain is a little past Killington. It was one of the first commercial ski resorts in the state.
  • Okemo Mountain is less than a 40-minute drive south of Woodstock.

top of a slope with one skier and large open view on mountains

View from the top of Killington

View from the top of Killington[/caption]

The Nordic Center, 1 mile from the B&B, offers 45 kilometers of beautifully groomed trails which span Mount Peg and Mount Tom.

Lessons and tours are available and should be booked in advance. Equipment rental on site.

Groomed snow trail on flat expanse with hills in the background

The Nordic Center offers groomed trails for cross country ski, fat bike and snow shoeing

Snowshoeing can be as peaceful or athletic as you want! It is a wonderful way to discover the outdoors right from the front door of our B&B when the snow blankets Woodstock! The trails at the Marsh Billings National Historical Park , on Mount Tom and Mount Peg, are wonderful for snowshoeing (trail fees apply). And after a snow storm, the town is your playground!

  • We have snowshoes and poles available to borrow. Simply bring a pair of waterproof, comfortable shoes, warm clothing, and you are on your way for some simple winter fun!
  • Or, head over to the Nordic Center, rent equipment there or bring your own, and enjoy miles and miles of groomed and marked trails. On Saturdays, the Nordic Center organizes a snowshoe trek to Mount Tom Cabin where a warm soup awaits!
vertical view of trees against blue sky Snowshoes in snow

Killington Mountain offers a multi-lane, lift-serviced tubing park open Friday evening, Saturday, Sunday, and holidays, starting Dec 21, 2019 to March 29, 2020 (conditions permitting). Check out their website for more information.

The tubing park is about 30 minutes from The Woodstocker.

On your way to Killington, why not stop at Shackleton Thomas or Farmhouse Pottery for some quality shopping or just to browse through the creations of high end artisans, and at Long Trail Brewery for a sampling of Vermont beer? On your way back, a pizza at Ramunto's could be just what you need -- or order it and enjoy it at the B&B!

laughing woman sliding down on a snowtube

With 2 departure locations less than 20 minutes from The Woodstocker, Snowmobile Vermont offers:

  • one-hour mountain tours that will take you through the woods on groomed ski trails.
  • two-hour back country tours on 25 miles of trails through the Calvin Coolidge State Forest, on the Vermont State Trails system, offering varied terrain.

Contact Snowmobile Vermont for more information and to book your tour. And get ready for some wicked awesome fun!




Fat Bikes are bicycles equipped with very large tires that grip the snow and ice, letting you tackle groomed trails going down or up. In Woodstock, they are available for rent at the Nordic Center. Group or semi-private tours are also available. Trail fees apply. Please click here for more information.

Vermont Bike and Brew  now offers electric fat bikes, which adds the convenience of an e-bike to the fun of a fat bike. Contact them to arrange delivery and discuss best trails. 

In 2018, Suicide Six hosted the first fat-biking slalom in the Eastern US.

Kedron Valley Stables in South Woodstock offers sleigh or carriage rides depending on the season and weather. Please call (802) 457-1480 to make your arrangements.

Billings Farms and Museum offers sleigh rides on select dates. Please check their website (https://billingsfarm.org/)


forest covered in red foliageThere are many trails around Woodstock, one of them starting right outside our B&B, up Mount Tom.

​If you’d like to take it up a notch with a local guide and hike to breathtaking views, we recommend an excursion to Luce’s Lookout with Wilderness Trails.

Simply add “Exciting Woodstock Outdoors” when booking your room, and we will contact you to arrange details.

Subject to availability and Mother Nature.

Tip: pre-order a fresh picnic from us for the day of the hike!

Fly Fishing

Guide and woman flyfishing in a lakeExperience the soul-soothing simplicity of casting a fly on a clear Vermont trout stream with The Vermont Fly Fishing School!

Vermont is known for its native brook trout, and fly fishing (catch and release) is perhaps the best way to discover Vermont’s pristine nature.

All equipment is provide
Option to take a basics pre-course
Offered from May 1st to October 31st, but is dependent on weather conditions

Price: Half-day on-stream trout fishing sessions are $180 for the first person, $60 per additional person (up to three people per guide), to be paid directly to The Vermont Fly Fishing School.

A Vermont fishing license is required, and can be purchased online.

Simply add “Exciting Woodstock Outdoors” when booking your room, and we will contact you to arrange details.

Subject to availability and Mother Nature.

Tip: pre-order a fresh picnic from us for the day of the fly fishing excursion!


 4 canoes on a lakeChoose between several options depending on the experience you are looking for:

​Connecticut River Float Trips for a more leisurely paddle
The Connecticut is great for those who want the big river experience without the rapids. The average trip time is 3 to 4 hours.
Price: Single kayaks $45 per boat; Double kayaks and canoes $70 per boat

White River Kayak Trips for more adventurous paddlers.
This beautiful river has light rapids and some little drops, so you might get wet!
Price: Single kayaks $45 per boat; Double kayaks $70 per boat

Dewey Mills’ Pond/ Ottauquechee river – Canoeing, kayaking, and fishing on a peaceful 100-acre wildlife sanctuary
Price: Single kayak $25 per boat; Double kayaks $70 per boat

North Hartland Lake for a lake experience. Great for birders and wildlife enthusiasts, this 1500 acre preserve and 3.5 mile long reservoir is located below Quechee gorge, and is maintained by the Army Corps of Engineers.
Price: Single kayaks: $35 per boat; Double kayaks and Canoes: $50 per boat
Add “Exciting Woodstock Outdoors” to your room when booking, and we will contact you to confirm details and book your excursion. You will pay the guide directly.

Subject to availability and Mother Nature.

Tip: pre-order a fresh picnic from us for the day of the hike!

Outdoor Experiences was last modified: June 2nd, 2024 by Isabelle Chicoine