Vermont 4-Day Bike Tour: Quintessential New England at Leaf-Peeping Peak (4 days)

Vermont 4-Day Bike Tour: Quintessential New England at Leaf-Peeping Peak

(4 days)


Cycle beside the Ottauquechee River and past historic Taftsville Covered Bridge to a cheese tasting at Thistle Hill Farm. Visit Vermont’s most well-known microbrewery, Long Trail, for a tour and tasting. Go leaf-peeping from the seat of a bicycle, feeling the warmth of the fall sun. Watch a glassblowing demonstration and dine at the riverfront flagship location of glassmaker Simon Pearce.


Not Included:

Lunch Included

Breakfast included for 5 days. As well as 5 day lunch and 5 day dinner. Ask travel specialist for more details.


All tours depart daily and are private, highly personalized and luxurious. Virtuoso travelers receive amenities and VIP treatment on all Artisans of Leisure tours.

Professional Guide

All tours include a guide to show you all there is to see on the tour.

Hotel Pickup & Drop-off

Private airport transfer for every Virtuoso member

Trip Itinerary

DAY #1 - Woodstock, VT United States Woodstock Inn
Your guides will greet you upon arrival in Woodstock and begin with a bike fitting and safety talk. Our first spin in the Green Mountain State takes us on wooded roads dappled with sunlight streaming through colorful canopies of leaves. Midway through our ride, we’ll pedal up to Thistle Hill Farm for a tasting of its famed Tarentaise cheese, inspired by cheesemaking traditions in the Savoie department of the French Alps. After sampling to our heart’s content, we continue cycling astride the Ottauquechee River, passing the historic Taftsville Covered Bridge before making our way back into Woodstock. A satisfying lunch at a quaint local café is followed by an afternoon of free time. This evening, toast to the days ahead over locally sourced dishes at the Inn’s celebrated Red Rooster restaurant.

Accomplished: 27 miles / 44 km, elevation gain: 2,752 feet / 839 meters
DAY #2 - Plymouth, VT United States Woodstock Inn
After an energizing breakfast, pedal south towards Plymouth on a route lined with rolling hills, sleepy farms, and babbling brooks. This quintessential Vermont village provides us with a glimpse of gentler times a hundred years ago, and we’ll sample delicious cheeses from the Plymouth Cheese Factory, one of the oldest in the country. After our tour and tasting, hop back on the and start the scenic ride towards Bridgewater. As we slowly descend toward the Queechee River, the views seem to get better and better. To cap off a delicious day, we’ll raise our pint glasses at Long Trail Brewery.

Accomplished: 43 miles / 69 km, elevation gain: 3,447 feet / 1,051 meters
DAY #3 - Windsor, VT United States Woodstock Inn
Today we set off along the banks of the Ottauquechee River until we meet Skunk Hollow Road. Flanked by the towering Green Mountains, we’ll pedal south on scenic roads that stream through sleepy Vermont towns to the base of Ascutney Mountain. From here, head back to Woodstock with a stop for lunch at the historic South Woodstock Country Store. Tonight, we revisit Quechee for an evening at Simon Pearce Glassworks. Shop for stemware, pottery, pitchers, and bowls, or simply watch the glassblowers at work. Our dinner here beside the river is as artful as the hand-blown glass shimmering all around us.

Accomplished: 35 miles / 56 km, elevation gain: 2,253 feet / 687 meters
DAY #4 - South Woodstock, VT United States Woodstock Inn
After your final breakfast in the region, join your guides for a short, scenic loop ride to cement your memories with a little leaf peeping! The morning light is our favorite for fall photos, so be sure to snap a few before spinning back to the hotel and bidding farewell to this beautiful corner of the world.

Accomplished: 9 miles / 15 km, elevation gain: 941 feet / 287 meters

Tour Pricing

11-13 People

From Tulum
$ 80 per person
  • Private Transportation
  • Entrance into Chichen Itza
  • Lunch
  • Tequila Tasting Tour
  • Cenote entrance
11-13 People
From Playa del Carmen
  • Private Transportation
  • Entrance into Chichen Itza
  • Lunch
  • Tequila Tasting Tour
  • Cenote Entrance
11-13 People
From Cancun
  • Private Transportation
  • Entrance into Chichen Itza
  • Lunch
  • Tequila Tasting Tour
  • Cenote Entrance


from $80/person

Payment Options

We accept Venmo, Zelle, Revolut, Cash App, or Credit Card.

Have a Question?

Feel free to reach out and we're happy to answer any questions you may have.

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