Self-Guided Walking Tours & Biking Tours

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Bike a loop around the Green Mountains of Vermont


  • Bike tour Vermont’s Green Mountains on rural roads and scenic byways
  • Visit the vibrant city of Burlington on the shores of Lake Champlain
  • Overnight at charming inns in quintessential Vermont villages
  • Relax with a cold microbrew and savor locally made cheeses
  • Explore Stowe, a year-round adventure hub at the base of Mount Mansfield

Bike the highlights of Vermont on this week-long tour encircling the Champlain Valley and the Green Mountains. Exceptional riding, local farm-to-table fare, fresh micro-brewed beer, and friendly communities make Vermont the perfect destination for a bike tour.

From vibrant Burlington, tucked between the Adirondack and Green Mountains, pedal along Lake Champlain through rolling farmland. Take in expansive views of forests and fields dotted by the white spire of a church steeple or the red side of a working dairy barn. Swing to the east to cross the Green Mountains via one of the renowned gap roads. Follow a scenic byway to the mountain town of Stowe at the base of the state’s highest peak, Mount Mansfield. With plenty of winding roads, swimming holes, and farm stands, Vermont will keep you enchanted both on and off the bike.

Day 1: Arrive Burlington

Fly into Burlington, Vermont, and enjoy your first evening in this lakeside city, meandering the brick pedestrian streets downtown and perusing the eclectic galleries and restaurants.

Overnight: Burlington

Day 2: Ride to Middlebury

Leaving the city behind, pedal past farm fields and views of the Adirondacks to the West and the Green Mountains to the east. Enjoy the charming villages of Shelburne, Charlotte, and Vergennes, offering plenty of options for a lunch stop. This region boasts many working dairy farms and has long been an agricultural and industrial center in Vermont due in part to Otter Creek, the state’s longest river.

Take time to enjoy Middlebury, a quintessential New England college town, with its historic mill buildings, centerpiece Otter Creek Falls, varied dining options, and boutique shops.

Ride: 43 mi +1380/-1180

Overnight: Middlebury

Day 3: Ride to Brandon

Today’s ride arcs to the west for views of Lake Champlain, a natural border between New York and Vermont. This route offers a morning of gentle valley riding before leaving the water behind and heading into the heart of the Green Mountain State.

Arrive in Brandon with time to explore the restaurants and shops or just relax for the night at your hand-picked inn. Historically a hub for building railroad cars, Brandon saw an economic boom that is evident by its elegant and stately homes.

Ride: 40 mi +1680/-1620 ft

Overnight: Brandon

Day 4: Ride to Waitsfield

Climb up and out of town today over one of Vermont’s famous pass rides, Brandon Gap. Although not the toughest or steepest of the Green Mountain gap rides, the ascent will challenge you and the downhill reward you with smooth pavement and the charming village of Rochester at the bottom.

Follow Vermont Route 100 north, as it slices through the Green Mountains and parallels the Mad River. Described by Yankee Magazine as one of the most scenic roads in New England, the route leads through picturesque villages, past wooden covered bridges, and offers more than one opportunity to indulge at a local sugar shack or ice cream bar along the way.

Ride: 43 mi +2580/-2280 ft

Overnight: Waitsfield

Day 5: Ride to Stowe, Free afternoon

Your day’s mileage may be shorter, but only so you have time to enjoy Stowe, the epicenter for Vermont’s mountain adventures. The town is not only famous for its winter activities like alpine and Nordic skiing, but also as a popular summer destination. Whether you’re interested in a hike, an afternoon browsing the artisan shops, or a visit to the Alchemist, an award-winning microbrewery, there are activities for everyone.

Ride: 23 mi +1180/-1220 ft

Overnight: Stowe

Day 6: Ride to Underhill & Transfer to Burlington

As you head west on meandering rural roads, you’ll find today’s ride quiet and rolling. Pedal through small towns, alongside clear rivers, and past the highest peak of the Green Mountains, Mount Mansfield. With pastoral vistas and lush green hills, the northern part of this loop does not disappoint! Once you’ve reached Underhill a short transfer will return you to Burlington.

Your final night offers countless celebratory options in Vermont’s colorful city, and a great opportunity to reflect on your week in this cyclist’s paradise.

Ride: 40 mi +/-2010 ft

Overnight: Burlington

Day 7: Onward Travel

From Burlington International Airport, choose to fly home or extend your trip in New England with a car, train, or bus trip from Burlington. Ask your destination specialist if you’re not sure which travel plans make the most sense for you.


Stay six nights in hand-picked B&Bs and inns, chosen for their character, comfort, and hospitality. The properties shown below are the ones we use most frequently. If we are unable to secure you a room in the following properties at the time of your booking, we will do our best to accommodate you in alternate accommodations which we have selected for their standard of comfort and will let you know this before we confirm your booking.

Solo Cyclists & Single Rooms

This trip is priced based on two people sharing a room. If you’d like separate rooms, a single supplement is required. This trip is also available to solo cyclists and a supplement is required. The friendly locals and small B&Bs make this a great trip to enjoy as a solo traveler.


Breakfast is included each morning. Typical breakfasts include juice, tea, coffee, yogurt, granola, breads, jams, eggs or a choice of hot dish. Please notify us of any dietary restrictions at the time of booking.

Lunch and dinner are not included so you are free to choose from the available options. Plan your day with this in mind; depending on your timing it may be easier to pack a picnic lunch, while at times your route will offer multiple cafes and dining along the way. There is information about available food and drink in your route notes.

Extra Nights

You can easily add extras nights during this itinerary. For further details, please ask us at the time of booking.




Lang House

Lang House

With an unbeatable location just steps from Burlington’s downtown, the Lang House retains its tranquility and charm, creating the perfect pairing of proximity and atmosphere.







Inn on the Green

Overlooking the Middlebury village green, this 1803 Federal-style building has been renovated to offer modern amenities in a traditional Vermont style, complete with breakfast delivered right to your room.







Lilac Inn

The cooked-to-order country breakfast might be the highlight, but it’s hard to choose at this romantic 9-room inn run by owners Doug and Shelley.







Featherbed Inn

Just outside the hubbub of Stowe, this peaceful rambling farmhouse offers spectacular views of Mount Mansfield, complete with an outdoor hot tub for enjoying them.







Brass Lantern Inn

Just outside the hubbub of Stowe, this peaceful rambling farmhouse offers spectacular views of Mount Mansfield, complete with an outdoor hot tub for enjoying them.





This trip is available May through October. There are some weekends in the spring (college commencement) and the fall (peak foliage season, college family weekends) when there is limited availability; please inquire with us and we will do our best to accommodate you. We suggest booking as far in advance as possible for a better chance at securing your dates.

When To Go?

New England’s seasonal changes are one of its greatest charms, and there are advantages to riding Vermont at any time of the year. May and June will bring fewer crowds, cooler temperatures (in the 50s-60s Fahrenheit), and lush green hillsides speckled with flowers. The summer months of July and August are busy with summer tourists, but the refreshing swimming holes, late summer evenings, and clear blue skies are worth it. Temperatures rise to the 70s-low 80s Fahrenheit on average with some hotter days. The crisp weather of September and October (in the 50s-60s Fahrenheit) draw not only outdoor enthusiasts to Vermont, but also the leaf-peepers and photographers, making it tough to secure reservations – but if you do, the colors of peak foliage season are pure magic.


Navigating is easy using the Macs Adventure Navigation App. Your daily rides will be mapped in the app with GPX tracks, route notes, and turn-by-turn directions. All of these resources are available to download for offline use, which is recommended as cell service can be unreliable in rural Vermont. Written turn-by-turn directions are included in the app. When you have cell reception, you will also have 24/7 telephone support from us here at Macs Adventure.

Experience, Fitness & Grade

This tour is graded moderate. The daily rides average 38 miles with an average daily ascent and descent of 1,770 feet. There are many rolling hills but the only sustained climb and descent is Brandon Gap, between Brandon and Waitsfield. You should be an experienced road cyclist accustomed to sharing the road with other users. At times the route has a shoulder, but its width varies, and some of the smaller, more rural roads have no shoulder. We advise high visibility clothing to be worn while riding.

The route is almost entirely paved, with infrequent and short gravel sections connecting rural roads. Surface conditions change yearly and seasonally, so gravel, pot holes, and frost heaves are a possibility. The distances and ascents/descent listed are approximations of the recommended routes.


Our pre-departure information pack includes a detailed equipment list on what to take with you. This includes warm and cold weather gear, cycling clothes, rain gear, and lots of other specifics. If you have any questions about what to take, we'd be happy to share our own top tips and advice.

Bike Rental

Bike rental is included in the cost of this trip. This includes a Trek Verve 1 or Giant Cypress, both comfortable hybrid bikes outfitted with a rack and water bottle cage. You will also receive a basic repair kit, helmet, and lock. If desired, Trek road bikes are available for an additional charge (models include Trek 1.1, Lexa, and Domane AL2). You can choose to use the flat pedals provided or bring your own clipless pedals and/or saddle to be installed on your rental bike. For a little extra assistance, e-bikes are also available (additional fee payable, subject to availability).

Please supply us with your height for your bicycle rental.

Travel Insurance

Travel insurance helps protect your travel investment, your belongings and most importantly you, from unforeseen circumstances that may arise before or during your trip. For more information, please visit our travel insurance page by clicking this link.



Getting to/from Burlington

The easiest way to travel to and from your trip is to fly in and out of Burlington International Airport. We can arrange a private transfer between the airport and your accommodation (additional fee payable).

Alternatively, you may opt to fly to a larger city and drive to/from Burlington. The drive will take 1 hour 45 minutes from Montreal, 3 hours from Albany, 3.5 hours from Boston, or 5 hours 45 minutes from New York City. You can return and pick up rental cars at several locations in Burlington, including the airport.

If you prefer public transport, there is a bus service (Megabus or Greyhound) from/to Boston South Station (about 4.5 hours). The Amtrak train is also a possibility, but involves a long trip so please plan accordingly.


  • 6 Nights in hand-picked B&Bs/inns
  • 6 Breakfasts
  • Bike rental
  • Baggage transfers between accommodations
  • Private transfer from Underhill to Burlington
  • Detailed pre-departure information pack
  • Turn-by-turn route notes
  • Macs Adventure Navigation App
  • 24/7 telephone support


  • Travel to/from Burlington
  • Lunches, dinners, snacks, and drinks
  • Travel insurance
  • Personal equipment


  • Additional nights before, during, or after your trip
  • Single room or solo cyclist supplement (if required)
  • Road bike upgrade

What happens if I can’t cycle a stage?

You will find contact information for local taxis in your pre-departure information pack. If you require a lift on one of your cycling days, please inquire ahead of time if possible. The luggage transfer company may be available to transport you to your next inn, dependent on their schedule. Fees apply to all additional transport. As always, if issues arise, Macs Adventure is only a phone call away.

How do I get my rental bike?

Your rental bike will be arranged through our local supplier at the starting point of your trip. We will set this up ahead of time and provide all necessary details in your pre-departure information packet. Our local bike supplier will deliver your bike to your hotel on the first morning of your trip and make any necessary adjustments. At the end of your trip, your bike will be picked up.

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