Meet your guides in Burlington for a quick transfer into the Champlain Valley. Here, we’ll meet Chef Matt Jennings at his restored barn and kick off the trip with lunch featuring products from his favorite local farms. Then it’s time for our first ride through Matt’s backyard, the agricultural breadbasket of Vermont. Stop in scenic Bristol for a creemee, the state’s beloved soft serve, then choose to transfer to our first hotel or opt for an extra climb over Lincoln Gap—widely considered the most challenging of the four passes that cross the mountains of central Vermont. Check into our picturesque inn in the heart of the Mad River Valley before tonight’s private dinner with the hotel chef.

Accomplished: 22 miles / 35 km, elevation gain: 1,879 feet / 573 meters

Longer Option: 37 miles / 60 km, elevation gain: 3,982 feet / 1,214 meters

Situated at the center of the state, the Mad River Valley’s reputation as a ski destination is well-known. But the summertime brings a whole different set of pleasures: a massive network of gravel roads lie parallel to the main corridor on Route 100, lined with farms that yield a staggering variety of local products: organic meats, small-batch cheeses, shiitake mushrooms, berries, and heirloom butter. Today is a veritable two-wheel farm tour as we bike with Matt around the valley meeting these producers, sampling their goods, and putting a face to a new generation of agriculture. The afternoon culminates in an al fresco lunch at a mountain farmstead. Bike back to Waitsfield to relax before joining Matt for a cooking class and dinner in an iconic Shaker barn.

Accomplished: 31 miles / 50 km, elevation gain: 3,244 feet / 989 meters

Longer Option: 45 miles / 73 km, elevation gain: 5,218 feet / 1,772 meters

Today we leave Waitsfield and follow bucolic farm roads through sleepy Randolph and Bethel, pausing for a coffee along the way. One final push brings us to the top of the ridge and right to our reward: a private picnic lunch prepared by Matt on a farm that makes high-quality ciders. Enjoy a tasting paired with Matt’s delicious spread before we part ways. Then, enjoy the downhill right into Woodstock, the quintessentially New England town where where our next charming inn is located. This evening, stroll the boutiques, antique stores, and specialty grocers in the Rockwellian town square, settling on a local restaurant for dinner on your own.

Accomplished: 31 miles / 50 km, elevation gain: 2,568 feet / 783 meters

Longer Option: 51 miles / 83 km, elevation gain: 4,205 feet / 1,282 meters

Pedal out of Woodstock along the Ottauquechee River, following one of our favorite hard-packed dirt roads as Vermont’s scenic farmland flows forth with picket fences, clapboard houses, and sprawling pastures all around us. We’ll reach Quechee for a visit to Simon Pearce Glassworks—shop for stemware, pottery, pitchers, and bowls, then get an up-close look at the glassblowers at work. Our lunch here beside a classic covered bridge and rushing waterfall is as artful as the hand-blown glass shimmering all around us. This evening, we’re treated to our final lovely farm-to-table dinner with our favorite local chef.

Accomplished: 27 miles / 44 km, elevation gain: 2,289 feet / 698 meters

Longer Option: 40 miles / 65 km, elevation gain: 4,107 feet / 1,252 meters

After a hearty breakfast, join your guides for a short, scenic loop ride or wake up with a leisurely stroll around the village of Woodstock. Your guides will transfer you back to downtown Burlington or to the airport as you bid farewell to this beautiful corner of the country.

Accomplished: Optional morning ride