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Cycle Vermont

Like a page ripped from a fairy tale, Vermont’s charm is simply undeniable. And when it comes to experiencing all the beauty this state has to offer, two wheels are better than four. Set out on a five-day cycling adventure through the Green Mountain State, discovering the quaint towns and gorgeous scenery that make Vermont so special. Follow an experienced leader along historic and scenic trails as they introduce you to hidden treasures and local favourites along the way.

5 days, from


per person


12 people max


Trip code: SSXV
Style: Original
Print itinerary


Countries Visited:  United States Of America
Accommodation: Simple Hotel/Motel (4 nights)
Transportation: Bicycle (e-bike option available , subject to availability) , Support vehicle
Meals: dinners, 4 breakfasts
Group size: Minimum 1, Max 12

  • Starting in bustling Burlington, swap city lights for peaceful nights as you cycle through rolling hills and verdant farmland towards the delightful town of Middlebury.

  • Visit the country’s smallest state capital, Montpelier, where you’ll pedal past the beautiful Vermont State House and stop by a family-run maple syrup farm.

  • Take on the Smugglers Notch Loop, a challenging climb followed by a freewheeling descent down through some of Vermont’s most charming towns.

  • Spend 2 nights in the idyllic New England village of Stowe, so beautiful even the Von Trapp Family call it home.

  • With a local leader to guide the way, you’ll find out what they love about Vermont and learn about the state’s history, culture and landscapes as you cycle.


Show Full Itinerary

Day 1: Burlington & Middlebury

Welcome to Burlington, Vermont! Despite being the state’s most populous city, it’s home to just 45,000 people, but when it comes to vibrant culture, green spaces and fantastic eateries, Burlington is up there with the best of them. Your adventure begins with a midday (12pm) welcome meeting, where you’ll link up with your local leader and fellow travellers joining you on your journey. If you arrive early, you may like to check out one of many restaurants and cafes serving up dishes made with locally grown ingredients, check out the Church Street Marketplace or take a stroll along the waterfront. After your meeting, hop aboard the support vehicle and drive to the nearby town of Charlotte (approximately 20 minutes). After a short bike fit and introduction it’s time to saddle up and enjoy your first ride in the rich environment of Vermont. Avoid the busy highways and ride south from Charlotte along quiet tree-lined by-roads and through rolling hills and lush farmland to Otter Creek, and into Middlebury where you’ll spend the night. With its white-steepled church, main street lined with quaint shops and excellent locally sourced dining options, Middlebury is your quintessential charming Vermont town – the perfect spot to get to know your group a little better over dinner.

Day 2: Cycle Montpelier to Stowe

After breakfast, jump into the vehicle for a pleasant morning’s drive through Vermont’s picturesque Green Mountains to the town of Montpelier, Vermont’s state capital and the smallest in the country (approximately 2 hours). Visit the Morse Farm Maple Sugarworks, an eighth-generation family-owned maple syrup farm, where you’ll learn about the maple syrup production process and of course sample some tasty maple products yourself. After getting your sugar fix, it’s time to ride down through the historic city of Montpelier and past the beautiful Vermont State House, the smallest capitol building in the USA. Follow your leader along the scenic Winooski River as it winds its way toward Lake Champlain. Leave the river behind at Waterbury – home to Ben & Jerry's bizarre and interesting ‘Flavor Graveyard’ – then turn north, riding up through the green hills past the Waterbury Reservoir before a gentle descent into the iconic town of Stowe. This is picture-postcard Vermont at its finest, with its white-spired church, weathered barns, covered bridge and multi-hued maple trees covering the nearby mountainside.

Day 3: Stowe & Smuggler’s Notch

Enjoy a morning ride through the small hamlet of Moscow before continuing on for your own taste of ‘The Sound of Music’ at the Enjoy a morning ride through the small hamlet of Moscow then continue on for your own taste of ‘The Sound of Music’ at the von Trapp Family Lodge, where the von Trapp family settled in the 1940s and their ancestors still work today. Perhaps enjoy a quick refreshment at the Von Trapp Brewery then follow the traffic-free Stowe Recreational Path as it winds its way gently uphill beside the West Branch Little River. To avoid the busy traffic and a lot of uphill riding, join your support vehicle for a short drive (approximately 10 minutes) up to the start of the Sterling Pond trail in Smuggler's Notch State Park. Here you’ll enjoy a beautiful hike up to the idyllic Sterling Pond before returning to the vehicle for the drive back down to Stowe.

Day 4: Smuggler’s Notch Cycle Loop

Today you’ll have the option to challenge yourself on the full Smugglers Notch Loop, or take it a bit easier and avoid 17kms uphill and 450m of climbing by hitching a ride in the support vehicle up to Smugglers Notch, then enjoying a freewheeling 13km descent down to Jeffersonville, an endearing New England riverside village. Perhaps stop for a quick coffee and pastry at the local greengrocer, then continue for 24 traffic-free kilometres along the Lamoille Valley Rail Trail, the longest rail trail in New England. Make a quick side-trip to the gorgeous Cambridge Junction covered bridge, then follow the river along the well graded, hard-packed and mostly flat gravel trail as it traverses through some of Northern Vermont’s most inspiring landscapes. Take a break in the historic village of Morrisville then take the small roads all the way back to Stowe.

Day 5: Cycle Stowe to Richmond

Start the day with a short drive (approximately 30 minutes) to Richmond then set out for a final ride across the undulating Green Mountains and past calm lakes before finishing on the shores of Lake Champlain. Enjoy a picnic lunch on a peaceful beach then reboard the support vehicle for the short drive back to bustling Burlington, where your cycling adventure finishes on arrival.

Unscripted experiences, insider access and authentic local flavors

Our team of travel specialists and local contacts have curated some of the best, most exclusive and authentic experiences, restaurants and accommodations in United States Of America to truly immerse yourself in a way that wouldn't be possible in larger groups or just on your own.

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