Trip Summary 7 Nights Avg miles per day: 30 – 50 Hill profile: Moderately Hilly! Cost: TBD ✔ I'm Interested

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 mid-September, just as the leaves are beginning to change. Expect cool mornings and nights, with comfortable daytime riding temperatures.

Enjoy a seven night 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. You will ride over the first (of many) covered bridges and will have the opportunity to taste Vermont maple syrup and tour the Grafton Village Cheese Farm. Don’t worry about having to lug back your purchases on the bike — we are happy to bring your purchases back to the Inn. Later on, we will have a group dinner in Chester.
Day 2	After a large country breakfast, we will set out to ride to Ludlow, Vermont. Along the way, we will stop at the Vermont Country Store in Weston. 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 elegant Castle Hill Resort and Spa. Relax by the heated pool and hot tub or schedule a massage or spa treatment. We end the day with a group dinner at the resort.
Day 3	We spend a second night at the resort. You will have the opportunity to go for a ride or just relax by the pool. We will have a group dinner at the resort.
Day 4	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 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 there are plenty of good restaurants within walking distance of our Inn.
Day 5	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. If you are interested, you can schedule a private tour of the Hall Art Foundation, a world class art museum along one of the day’s cycling routes. There are also hiking trails nearby. As we will be spending a second night in Woodstock, you will have the opportunity to try another fine restaurant on your own.
Day 6	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, but end back in Vermont in the lovely town of Springfield. We will have a private tour of the underground tunnels and Telescope Museum at the historic Hartness Inn in Springfield, Vermont and enjoy a group dinner at the Tavern.
Day 7	We head back over to Chester, with a stop at the Jersey Girls Dairy Farm for a guided tour of this farm that uses rotational grazing and free space barns…and yes, they make delicious cheeses that we can taste and buy. After the farm stop, we will end the tour back in the town of Chester, where we will stay one more night at the Fullerton Inn and enjoy our final group dinner.
Day 8	Our tour ends after breakfast, although you can stick around and do one of the extra rides that we provide.

Day	Route	Miles	Ascent
1	Chester, Bellows Falls Loop Chester Loop	41 27	2000 1400
2	Chester to Proctorsville Chester to Proctorsville	38 22	3100 1500
3	Proctorsville Loop	TBD
4	Proctorsville to Woodstock – long Proctorsville to Woodstock – short	47 31	2100 1500
5	Brownsville Loop Pittsfield Loop Pomfret Loop Pomfret Strafford Loop	38 56 26 58	2200 2500 1700 4100
6	Woodstock to Springfield Long Woodstock to Springfield Medium Woodstock to Springfield Short	45 37 34	2500 2400 2000
7	Springfield to Chester – long Springfield to Chester – short	34 13	1600 900

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.

✔ I'm Interested

What is included?

• 7 nights lodging
• 5 breakfasts, 5 dinners
• Routes
• Luggage transport
• SAG support
• Tandem bike case storage, if needed
• Guided tour of the Jersey Girls Dairy Farm
• 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 30-50 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:

• The Fullerton Inn
• Castle Hill Resort & Spa
• The Woodstock Shire Inn
• The Hartness House Inn & Tavern