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Vermont Chef on Wheels Bike Tour

Farms, Food, and Foliage Featuring Chef Matt Jennings

5 days / 4 nights Level: 3Collection: Classic, Specialty

Tour Highlights

  • Ride across the Green Mountain state from the rich farmland of the Champlain Valley to quaint New England destinations like Waitsfield and Woodstock
  • Roll up your sleeves with renowned chef Matt Jennings for a cooking class and dinner in a beautiful Shaker barn
  • Spend two nights in the heart of Woodstock, Vermont’s most picturesque small town, characterized by covered bridges, boutiques, and innovative restaurants
  • Visit local farms to sample produce, cheeses, cider, and more, and get to know the people paving the way to a culinary revolution
  • Step into Chef Matt’s world with a healthy lunch at his house and barn kitchen, followed by a ride on his favorite local roads


Organic cheeses, the finest grades of maple syrup, free-range meats, artisanal bread, and garden-fresh vegetables


World-famous micro-brews and apple cider

As featured in:
Print Itinerary
  • Day 1

    The Champlain Valley

    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.

    Meals: Lunch / Dinner
    Destinations: Bristol, Lincoln, Waitsfield
    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
    Accommodations: The Inn at Round Barn Farm

  • Day 2

    Exploring the Mad River Valley

    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.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Waitsfield, Warren, Sugarbush
    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
    Accommodations: The Inn at Round Barn Farm

  • Day 3

    Waitsfield to Woodstock

    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.

    Meals: Breakfast / Lunch
    Destinations: Randolph, Bethel, Woodstock
    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
    Accommodations: Blue Horse Inn

  • Day 4

    Quechee Loop

    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.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Pomfret, Hartford, Quechee
    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
    Accommodations: Blue Horse Inn

  • Day 5

    Country Roads

    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.

    Meals: Breakfast
    Destinations: Burlington
    Accomplished: Optional morning ride

DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.

Arrival Details

Airport City: Burlington, Vermont Pick-Up Location: Hotel Vermont or Burlington Airport Pick-Up Time: 10:30 am
Departure Details

Airport City: Burlington, Vermont Drop-Off Location: Burlington Airport Drop-Off Time: 12:30 pm
Meet the Chef: Matt Jennings

Celebrated chef, cookbook author, and avid cyclist Matt Jennings got his start in the food world as a 15-year-old prep cook and stock boy at a café in his native Massachusetts. After graduating from the New England Culinary Institute with distinction, Jennings worked at notable restaurants around the country and abroad before opening Farmstead in Providence, Rhode Island, where he garnered four James Beard Foundation nominations. In 2014, he returned home to Boston and opened Townsman—a New England Brasserie concept that was named “Restaurant of the Year” in 2016 by Food & Wine Magazine. Today, Jennings lives on a farm in Vermont’s Champlain Valley with his pastry chef wife, Kate, and their two sons. Together, they raise chickens, pigs, and sheep and operate Red Barn Kitchen—a state-of-the-art commercial kitchen and retail store devoted to fresh, seasonal produce and farm-to-table cuisine.

Travelers Take Note

Some of the riding will take place on packed dirt roads.

COVID-19 Travel Restrictions

For the latest travel restrictions related to the coronavirus pandemic⁠—including quarantine requirements—please review Vermont’s state travel guidelines. Proof of full vaccination (including booster) is required to join this tour.

Weather by Month

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  • Thoughtfully selected accommodations that reveal the true character of the region
  • Luggage transfers


  • Daily breakfasts, all lunches, nutritious snacks, and après velo cocktails
  • 3 gourmet dinners at our favorite local restaurants and renowned culinary establishments
  • Carefully selected local wine, beer, or spirits with every meal


  • Wine tastings and activities as outlined in the tour itinerary
  • Entrance fees to historic sites, museums, parks, and all other exclusive events
  • Gratuities for baggage, porters, and hotel service


  • Top-of-the-line bicycle selection
  • Bike helmet
  • Complimentary DuVine gear, including a custom cycling jersey, DuVine t-shirt, water bottle, and drawstring bag
  • GPS in most destinations


  • Expert bilingual guides with extensive local knowledge
  • Support vehicle that follows the day’s route, distributes refreshments, and offers lifts
  • Pick-up and drop-off before and after your tour from predetermined meeting points
  • Daily bike maintenance to ensure optimal performance

See our FAQs page for answers to common questions.

See FAQs

Custom DuVine Road Bike

Manufacturer: Ventum

Type: Road

Quick 1 Disc

Manufacturer: Cannondale

Type: Hybrid

Turbo Vado SL 4.0 EQ

Manufacturer: Specialized

Type: E-Bike