“I love Vermont because of her hills and valleys, her scenery and invigorating climate, but most of all because of her indomitable people.“Calvin Coolidge
Vermont is the number one state in the US for bicycle touring. The relatively low population, the cute small towns, the green forests, and the opportunity to sample and purchase locally-made products make for an extraordinary vacation on two wheels.
But Vermont is not called The Green Mountain State for nothing! Much of the state is hilly. In fact, it is really only the far western portion of the state in the Champlain Valley that one can find moderate cycling. This is where our tour takes place. In the southern end of this verdant valley, you will enjoy days of biking on rolling country roads with wide-open agricultural vistas, and an array of quaint small towns.
If you ride the main routes each day, you will ride from inn to inn, never having to see the inside of our support vehicle. Our routes are almost entirely paved and mostly very low traffic. We start and end in the town of Middlebury, Vermont, the state’s most famous college town. We also stay in Brandon, which has what the New York Times dubbed “the prettiest street in Vermont”, and the farming village of Shoreham – population 800 but boasting a 220-year-old country inn. If you drive to this tour, you can park your car at the beginning, return to it at the end, and enjoy five days of being outside in wonderful Vermont.
As on all our bicycle tours, you get to choose from two or three routes each day of different distances. We provide electronic route directions you can upload on your cell phone but if you don’t like using those (we think you will) you can always just stick with others in the group. You can bring your own bike or rent from us and we even have e-bikes available. We’ll ride past apple orchards, horse farms, and covered bridges en route.
Come join us in Vermont to see why it is truly is the best bicycle touring location in the country.
Private Tour Info
Want to make this trip even more memorable? Grab your friends and pick a date.Start planning your private tour
- Cost Per Person: $2,700
- Single Supplement: $600
- Private Tour Minimum: 8
- Activities: Biking
- Difficulty: All Abilities
- Guides: Kim Thompson, Luis Laciar
Other Info: Optional hybrid bike rental is $38/day for four or five days. You may upgrade to a road bike for $50/day or an E-bike for $65/day.Book this Tour
- Explore the cute villages of Brandon, Middlebury, Vergennes, Bristol, and Shoreham
- Check out the seven beer, wine, spirits, and cider makers on the Middlebury Tasting Trail
- Pretend you are on horseback in the 1800s as you ride through one of multiple covered bridges in the area
- Cycle past rolling farmlands and lush orchards and then sample the bounty of wares produced
- Take an historical walking tour of the village of Middlebury, considered the college town of Vermont
We meet as a group at 10:00 AM in Middlebury, Vermont, an hour south of Burlington - we can pick you up in Burlington if you fly to Burlington airport. Middlebury is one of the hippest small cities in Vermont, with only 8,000 residents but home to Middlebury College, which gives it a great cultural scene. If you are renting a bike, we'll introduce you to your steed and fit it properly. We'll then do an introductory loop ride northeast to the town of Bristol, a small village located in the valley snuggled up against the Green Mountains. With an old fashioned main street full of shops and restaurants, Bristol makes a great stop en route. Back in Middlebury, we'll check into our hotel, a renovated inn dating back to 1827, and eat at Morgan's Tavern.
Distance: 12 or 25 Miles
We'll start the ride today passing through the traditional farmland famous for this area of Vermont. You'll see corn fields, dairy farms, maple syrup cottages, and many more agricultural businesses. We'll then head south under the western edge of the Green Mountains, making our way to Lake Dunmore in Branbury State Park. If you wish, you can stop to enjoy a hike in the park or nearby Moosalamoo National Recreation Area. As we near the end of the route a favorite stop is Foley Brothers Brewing, just outside our destination of Brandon. Brandon is a cute small town of 4,000 inhabitants and you'll have time to walk Park Street (the cutest street in Vermont according to a New York Times writer), stop into the Center Street Bar for a drink, or grab a bottle of wine at Gourmet Provence for after dinner. Dinner tonight is at the Brandon Street Inn, our home this first night.
Distances: 25, 29, or 39 Miles
After breakfast, we are off on our bikes, past active dairy farms and apple orchards, with glimpses of fall foliage colors on the trees in the foreground and the green of the Adirondack Mountains of New York in the back. You will have multiple route options today with some of them passing through Orwell, a small village with a country store that looks classic on the outside but offers a modern take on lunches on the inside. For longer routes, you can cross over Lake Champlain on a seven-minute ferry ride to visit Fort Ticonderoga in New York. Our ultimate aim is the small town of Shoreham and the Shoreham Inn, where we'll eat dinner in its Euro-style pub.
Distances: 16, 33, or 46 Miles with an optional 25 mile loop extension
After a delicious breakfast at our inn, we again jump on our bicycles. There are a few hills to get over in the morning - you can use the shuttle van if you wish - and then we'll be on rolling farmland for much of the day. Most of our routes are way off the beaten path, meaning you'll be more likely to have a conversation with a farmer (or her cow) than you are to come across a coffee shop. However, one stop on some routes is the lovely town of Vergennes, which makes for an excellent lunch stop. As you approach Middlebury, you can stop into the famous Morgan Horse Farm. Or visit one of the seven wineries, breweries, cideries, or distilleries on the Middlebury Tasting Trail. We will celebrate our final dinner of the tour in a nearby restaurant famous for its locally sourced cuisine.
Distances: 18, 27, 36, 49, or 63 Miles
On this, our final morning, we put away our bikes and take a walk around the town of Middlebury to see the historic Marble District and the falls of the river that runs through town. We'll return to the hotel for a shower and to check out. You can catch our shuttle back to the airport or jump in your car to continue your journey. (Note on some tours we will actually stay in the cute small town of Vergennes the final night and cycle from Vergennes to Middlebury on the final morning.)Book this Tour
NIGHTS 1 & 4 >> MIDDLEBURY INN / MIDDLEBURY, VT
Since 1827 the Middlebury Inn has overlooked the central green of the town. You can enjoy a glass of wine or local beer while sitting on the front porch and watching the world go by.
NIGHT 2 >> BRANDON INN / BRANDON, VT
The Brandon Inn is located just across from the village green in the heart of this classic Vermont village, known both for its architecture and artistic community. It was voted the Best Historic Inn in Vermont in 2017.
NIGHT 3 >> SHOREHAM INN / SHOREHAM, VT
A 200-year-old building, the Shoreham Inn has centuries of history as the mainstay of the small community of Shoreham, population 800. Run by the lovely couple Andrew and Elizabeth and boasting a pub and restaurant onsite, it is in the heart of the best cycling in Vermont.Book this Tour
Arrival & Departure
If you are driving to the tour, we will meet you just after lunch in Middlebury, Vermont. You can leave your car there as you will not need it during the tour. If you are flying to the area, we will pick you up at the airport in Burlington and drop you back off on the last day of the tour.
- At least one Zephyr guide accompanies each trip and a second or third is added as necessary.
- Our trip prices are based on double occupancy. If you are coming on a trip solo, you have two options: 1) Pay the single supplement to receive your own room. 2) Ask us to try to find you a roommate of the same gender to share a room with; if we are not successful you will be charged the single supplement and receive your own room.
- All of your dinners and breakfasts are included. Gratuity for these meals is also included. In general, we leave lunches open so that you have time to explore and enjoy the local flavors en route.
- All your transportation is included once you meet your guides on the first day.
- NOT INCLUDED Beverages, desserts, lunches, gratuities to your guides, personal expenses and travel to and from the destination.
The biking season in Vermont runs from about mid-May through mid-October. By the time our tour starts in mid September, average highs will be down to the mid 60s - perfect for cycling. It does rain or snow in Vermont pretty much year-round (that is why it is so green) so be prepared and we'll adjust as needed. Nights should be pleasantly cool and we should see the start of the fall foliage leaf color show.
Extending Your Stay
You will need a car if you wish to extend your stay in the area. Since fall is peak season, we suggest you make hotel reservations in advance. One nice town we don't visit is Stowe, at the base of Vermont's tallest mountain. Burlington is also a fun city worth spending a night or two. Since the fall foliage season will likely still be waxing, we suggest you extend your stay after our tour and consider getting into the mountains where the leaves will just be turning.
Changes to Your Itinerary
While everything under “What is Included” will remain the same, the actual restaurants, hotels, and activities listed in our itineraries are subject to modifications. Changes that are out of our control are common – a restaurant closes or loses its awesome chef, a winery changes its visiting hours, a hotel gets remodeled, a road or trail undergoes construction. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes (even at the last minute, during the guides’ scout trip) to the itinerary that will improve your overall trip experience. If there is any one experience that is going to make or break your trip, please discuss this with us in advance! We will attempt to keep our website itinerary as current as possible and communicate any major changes with you in the weeks prior to the tour.
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