Trip Summary8 Nights Cost: $8,500/team |
If when you think of Vermont and New Hampshire, you think of quiet country roads, covered bridges, micro-breweries, wineries, maple syrup, homemade cheeses, sustainable farming, warm hospitality in country inns and spectacular scenery with a few hills thrown in, you are in luck! Oh, and as an added bonus, we will also throw in exploring the birthplace of our 30th President (we know you wanted to visit the birthplace of Calvin Coolidge)!
We start the tour in late-September, just as the leaves are beginning to change. Expect cool mornings and nights, with comfortable daytime riding temperatures.
Enjoy a eight night/nine day tour of Vermont/New Hampshire.
Here is our detailed Itinerary of the tour:
| Day 1 |  Our tour starts in the charming town of Chester, Vermont. We will meet in the early afternoon. After a brief orientation, we will offer rides in the picturesque country roads surrounding Chester. Later on, we will have a group dinner in Chester. |
| Day 2 |  After breakfast, we will offer a ride that goes south of Chester. You will ride over the first (of many) covered bridges and will have the opportunity to stop at the Vermont Country Store. Don’t worry about having to lug back your purchases on the bike — we are happy to bring your purchases back to the Inn. Dinner is on your own in Chester. |
| Day 3 |  After a large country breakfast, we will set out to ride to Proctorsville, Vermont. Lunch is on your own in one of the many small towns that we will be passing through. We will stop at the picturesque Buttermilk Falls where you can take a short hike to see the falls. We will meet up in the afternoon at the Pointe at Castle Hill. We end the day with a group dinner at the resort. |
| Day 4 |  We spend a second night at the Pointe. You will have the opportunity to go for a ride or just relax and avail yourself of a spa treatment or take a swim in the resort’s indoor pool. We will be staying in large suites that each have a washer/dryer, so today would be a good opportunity to do some laundry! We will have a group dinner at the resort. |
| Day 5 |  After another breakfast, we will set off with a stop at the Plymouth Notch Historic District, including the birthplace of President Calvin Coolidge. We will continue to lunch and a self guided tour at the Long Trail Brewing Company in Bridgewater Corners, Vermont along the bank of the Ottauquechee River. We end the day in the town of Woodstock where we will enjoy a group dinner in one of the fine restaurants within walking distance of our Inn. |
| Day 6 |  You can ride as much — or as little — as you want. You can even sleep in! We will be spending a second night in Woodstock. Breakfast in Woodstock will be on your own as there are several lovely cafes and restaurants within walking distance from the Shire Woodstock Hotel. We will offer rides of varying lengths. We encourage you to visit the galleries and shops in the town of Woodstock, the Rockefeller National Historical Park and the Billings Farm and Museum — all within easy walking distance of the Inn.
There are also hiking trails nearby. Dinner tonight is on your own in one of the many lovely restaurants in Woodstock. |
| Day 7 |  After breakfast on your own, we set off again with our ride stopping at the Simon Pearce Gallery to see glass artisans at work at one of the most beautiful waterfall settings…and what is a day of Vermont cycling without another tasting? This one is at the Silo Distillery in Windsor, Vermont. You will have the opportunity to tour the Artisan Park in Windsor, including shops, the Harpoon Brewery and the Path of Life Sculpture Garden. We also highly recommend a stop at the American Precision Museum on the site of the first US factory at which precision interchangeable parts were made. We then cross into New Hampshire for some riding ending at the Common Man Inn in Claremont, New Hampshire. Dinner is on your own in Claremont. |
| Day 8 |  We offer a loop ride from the hotel. Our loop ride will take you to the historic towns of Newport and Sunapee. We will also offer a loop to the Hall Art Foundation, a modern art museum in Reading, Vermont. If you are looking for more adventure, check out the Superman Zip Line Tour at the nearby Morningside Park. We will enjoy a group dinner on this, our final evening together.
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| Day 9 |  After breakfast, we will ride back to Chester. If you drove, you will be reunited with your car. Our tour ends once you arrive in Chester. |
| Day | Route | Miles | Ascent |
| 1 | Chester Springfield Loop | 21 | 1400 |
| Chester Londonderry Loop | 43 | 3200 | |
| 2 | Chester Loop | 27 | 1400 |
| Chester Bellows Falls Loop | 41 | 2000 | |
| 3 | Chester to Proctorsville – short | 23 | 1600 |
| Chester to Proctorsville – long | 38 | 3100 | |
| 4 | Proctorsville Loop – short | 28 | 2000 |
| Proctorsville Loop – long | 48 | 3200 | |
| 5 | Proctorsville to Woodstock – short | 32 | 1500 |
| Proctorsville to Woodstock – long | 47 | 2100 | |
| 6 | Woodstock Pomfret Loop | 26 | 1700 |
| Woodstock Brownsville Loop | 38 | 2200 | |
| Woodstock Pittsfield Loop | 56 | 2500 | |
| Woodstock Pomfret Strafford Loop | 58 | 4100 | |
| 7 | Woodstock to Claremont – short | 27 | 1100 |
| Woodstock to Claremont – long | 35 | 2200 | |
| 8 | Claremont Sunapee Loop – short | 32 | 2000 |
| Claremont Sunapee Loop – long | 41 | 2400 | |
| Claremont Hall Art Loop | 31 | 1800 | |
| 9 | Claremont to Chester – short | 27 | 1900 |
| Claremont to Chester – long | 40 | 2100 |
As with most of our tours, we limit the size of the tour to a maximum of ten couples. We plan to open this tour in mid-2025. Please click below if you are interested in this tour. We will let you know as soon as the tour opens.
What is included?
- 8 nights lodging
- 6 breakfasts, 5 dinners, 1 lunch
- Routes
- Luggage transport
- SAG support
- Tandem bike case storage, if needed
- Cheese, maple syrup tastings
- Beer and spirit tastings
What is not included?
- Transportation to the start point
- Meals, other than those mentioned above
- Alcoholic beverages
- Admission to points of interest not referenced above
Note that we do not provide any bicycles. We expect that you have a tandem that is in good working order and that you are able to assemble your bike. If you do not have your own tandem, you can rent a coupled tandem from Mel at Tandems East. Mel also sells tandems, so if you end up renting from him, you might get a discount if you purchase a bike from them. If you have a tandem that is not coupled, it is possible to bring it, but you should make sure that all of your flights could handle the larger box.
What is the average mileage per day?
As there is a lot to see each day, average mileage will be in the 25-50 mile range. We can certainly add routes for those that would like to do more riding. We can also shorten some days if you want. This area is a perfect area to host a trip as there are great roads, but lots of attractions as well. There are some hills — just let us know what you like!
While this can change, this is where we plan to be staying:
- Inn Victoria or Chester Inn
- The Pointe at Castle Hill Resort & Spa
- The Woodstock Shire Inn
- The Common Man Inn