Vermont and a little bit of New Hampshire

Trip Summary

6 Days / 5 Nights
Avg miles per day: 30-40
Hill profile: some hills

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, 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)!


Enjoy a five night/six day tour of Vermont/New Hampshire.

We will be capping each group at ten teams.

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.

After a large country breakfast, we will set out on Day 2 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 Inn at Waters Edge, along the shore of Echo Lake where you can swim, play horseshoes and bocce. We end the day with a group dinner at the Inn and maybe a game of billiards!

After another country breakfast, we will set off on Day 3 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.

You can ride as much — or as little — as you want on Day 4. 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.


We set off again on Day 5, 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 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 on this, the last night together.



On Day 6, 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 you can continue your vacation either by staying another night or continuing on to the Eastern Tandem Rally.


What is included?

  • 5 nights lodging in hotels, country inns and bed and breakfasts
  • 3 breakfasts, 1 lunch and 3 dinners
  • Routes
  • Luggage transport
  • SAG support
  • Tandem bike case storage, if needed
  • Parking behind the Fullerton Inn in Chester, if needed
  • Admission to the Calvin Coolidge Homestead and State Historic Site and the Marsh-Billings Rockefeller National Historic Park.
  • 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
  • Registration for any rally that you are attending before or after the tour

What is the average mileage per day?

As there is a lot to see each day, average mileage will be in the 30-40 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!

Where will we be staying?

How do we sign up?