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Bike Tour of the Adirondacks and Vermont

A Six Day Cycling Vacation of the Southern Adirondacks and Vermont

Adirondack wilderness, verdant Vermont farmland, and the upper Hudson River Valley give the cyclist a lot to see in six days of cycling on this new tour.  Covered Bridges, majestic views, quaint small towns and pristine lakes are just of few of the pleasures.  Come join us as we explore some of the prettiest areas of two states.

This tour destination is available for private groups in 2020.   September is a great month to choose.  Contact us soon to starting planning for your group.

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Adirondacks & Vermont

Saratoga Springs, NY, Chestertown, NY, Brandon, VT and Manchester, VT

Tour Difficulty

Hilly Terrain, with a few Challenging Climbs


6 Days, 5 Nights


Friends Lake Inn, Chestertown, NY

Nearest Airport

ALB Albany International


From $2295 per person


9/8/19 - 9/13/19 9/15/19 - 9/20/19
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I enjoyed the scenery most - it was gorgeous. A challenging ride for strong riders through spectacular New England country sides.
Robby, Bethesda, MD

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Day 1

33–45 miles, hillly, with a few challenging climbs

Meet the group in either Saratoga Spring for a courtesy shuttle, or at the home base for the night, Friends Lake Inn.  Quickly we will be on country roads leading into the Adirondacks.  Valley roads and a few short climbs will take us by babbling streams, lake views, and forested land.  Arriving at Friends Lake Inn by early afternoon, there will be time to relax and enjoy the beautiful inn.  The inn has canoes and kayaks for exploring Friends Lake, hiking trails, and a pool and sauna.

Later we'll reconvene for dinner onsite at Friends Lake Inn's acclaimed restaurant. 

Day 2

37–58 miles, hilly, with a few challenging climbs

It is a big ride today that takes us from the Adirondacks, across the southern end of Lake Champlain, and into southern Vermont.  Included is a short ferry that takes us from the Empire State to the Green Mountain State.  From there, the ride introduces beautiful Vermont farmland between mountain ridges.  You'll arrive in the quaint town of Brandon where you may want to grab a quick ice cream cone on the town square before checking in at the outstanding Lilac Inn a block away.  Brandon bills itself as the "Art & Soul" Village of Vermont.  It is what you might expect of a Vermont village: a vibrant, walkable center of art galleries, studios, shops and restaurants.  Pop in the Brandon Museum, which also happens to be the birthplace of Stephen A. Douglas.

Day 3

30–65 miles, hilly, with a few challenging climbs

As our layover day, you will have opportunities to bike a little, a lot, or not at all.  The recommended route will include beautiful Middlebury, VT, home to Middlebury College and a charming downtown area.  Along the way, pass through a covered bridge, and take a short walk to a beautiful waterfall.   In the village center is the cascading falls of Otter Creek, where the town grew around a series of water driven mills.  Pause here for lunch on your own at any of the many downtown Middlebury options, including the historic Marble Works.  Amongst the beautiful stone and marble, you’ll find an eclectic mix of businesses, including restaurants, and River Front park, which offers the best view of Middlebury’s falls.  You may also opt to hammer your way back to Brandon for lunch there.

Back in Brandon, take some time to browse local shops and relax on the grounds of the Lilac Inn.

Day 4

29–57 miles, hilly, with a few challenging climbs

Leaving Brandon behind, we'll pedal south through gorgeous Vermont countryside on our way to Manchester.   If you are a fan of covered bridges, this is your day!  At least 4 of them will be included in your route.  Also along the way, you will pass through Vermont marble country.  The Vermont Marble Museum is on the route so that you can learn more about the importance of local marble industry and see creative works that have been carved into marble over the years.  Pause for lunch in Middletown Springs at Sissy's Kitchen.  This is one of the great stops in all of Vermont for fresh local ingredients and delicious sandwiches, soups, salads and baked goods.  Also check out the garden and the antique shop in the barn out back.  Late afternoon, you'll reach the upscale tourist town of Manchester in time to explore retail opportunities and museums.  Dinner is included at the spectacular Reluctant Panther restaurant nearby.

Day 5

40–53 miles, hilly with a few challenging climbs

Today we bicycle to Saratoga Springs from Manchester.  The route will follow the Batten Kill River part of the way.  The Batten Kill River Valley is a favorite area for local cyclists.  Beautiful rolling farmland greets us as we return to New York, then cross the Hudson River on the way to Saratoga Springs.  On the way, take a break at the Saratoga Monument.   It contains large bronze plaques of stylized views of the Revolution.  The Monument was built in 1877-1888 and dedicated in 1912 to commemorate where the British General Burgoyne surrendered.  A ranger is available for brief talks at the monument, now part of Saratoga National Historical Park.  The talk and the climb up and down the 155-foot granite monument totals about 30 minutes.  The view from the top offers a perspective of the farmlands and countryside where the Continental Army battled and the history of the world took a sharp turn towards liberty.

Saratoga Springs is a booming town famous for horse racing.  “Health, History, Horses” is the town slogan.  Health in the healing mineral waters, history includes the Battles of Saratoga, and horses at the Saratoga Race Track.  There are 17 public mineral springs which offer naturally carbonated, mineral-rich waters famed for their health benefits.  By the mid-1800s, healing springs tourism led to the growth of Saratoga Springs.  Today, one location for mineral baths is the Roosevelt Baths at Saratoga Spa State Park, certainly an option after a long bike ride!

Dinner tonight will be a short walk away in downtown Saratoga Springs.

Day 6

21–40 miles, rolling hills

Our loop ride today takes us to Saratoga National Battlefield Park.  You may want to take in the Visitors Center.  After breakfast, we will take a ride through nearby rolling countryside.  Along the way, we will pedal though the Saratoga Battlefield on the banks of the Hudson River.  Visit the National Park Service visitor center for insight into the events that took place here in 1777.

As always, showers and lunch will be provided before departure.  Shuttle available to Albany International Airport for those flying.


$2,295 - $2,395
Bicycle Rental
Single Room Supplement

Low end of tour price range reflects the 6 month Early Bird Discount.  High end of price range reflects no Early Bird Discount. 

What's Included in Your Tour Price


5 nights at boutique inns and lakefront resorts


Dinner on Nights 1, 2, & 4; All lunches except 1; All breakfasts; Snacks; and Hors d'eourves most nights.

Services of Expert Guides

Carolina Tailwinds maintains a guest to guide maximum ratio of 7:1 on all our tours.  Guides are ready to show you the hidden wonders of each and every destination.

Full Route Support & Luggage Transfer

Service of 1 – 2 support vans on route every day.

Complimentary Airport Transfer from Albany or Saratoga Springs

A courtesy shuttle will be provided on the morning of Day 1 to Friends Lake Inn from both the Albany Airport Area and Saratoga Springs.  The pickup times are 8:30-9:00 a.m. in the Albany Airport area and  9:45 in Saratoga Springs. 

We terminate our cycling in Saratoga Springs, NY on Day 6.  Return transfer to the Albany Airport area is provided in the late afternoon on Day 6. 

More details on what's included: 

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Friends Lake Inn

Night 1

Friends Lake Inn963 Friends Lake Rd., Chestertown, NY 12817 518-494-4751
On a pristine Adirondacks lake, this boutique hotel offers luxury accommodations in a rustic country setting. There are 17 guest rooms, many with Jacuzzi tubs, lake views and fireplaces.  The highly acclaimed restaurant serves innovative New-American cuisine complemented by a superior wine collection, served in the warmth of a 19th century dining room.  TripAdvisor Certificate of Excellence winner.

Lilac Inn

Nights 2 & 3

Lilac Inn53 Park St., Brandon, VT.  

Park Street is called by some "the prettiest street in Vermont." Brandon is an unspoiled, unhurried village.  The inn is a beautiful Greek Revival mansion built in 1909 and meticulously modernized.  Lilac Inn also serves excellent meals in both a formal dining room and a more relaxed tavern space.  Recommended by Karen Brown's World of Travel.

Inn at Manchester

Night 4

The Inn at Manchester3967 Main Street Manchester Village, VT 05254 (802) 362-1793
This Select Registry Inn is walking distance to the shops, restaurants and museums of Manchester, VT.  Just a few steps away is the American Museum of Fly Fishing and and Orvis Flagship Store.  Of course, you may just want to stay put and enjoy the pool and beautiful four acres of grounds at the inn.

Union Gables Inn

Night 5

Union Gables Inn 55 Union Ave, Saratoga Springs, NY, 12866 
A stunning heated outdoor pool, rose gardens, fountains, sitting areas and classic wrap around porch that boasts a quiet haven to immerse in the history of the surrounding area. Elegant and spacious rooms have private bathrooms, fireplaces, flat screen televisions.  A full cooked-to-order breakfast is served daily.



The terrain is a mix of rolling hills and a few challenging climbs, making it appropriate for intermediate and advanced riders.  Daily distances of 40-65 miles inn to inn.  Typical daily cumulative climbing will be in the 2,000 - 4500 feet range.  As with all Carolina Tailwinds tours, there will be multiple opportunities for "leap-frog" shuttles to shorten and/or flatten the route.  Road bikes and lightweight hybrid bikes with a wide range of gearing are recommended. 

Tour Point of Origin:

Friends Lake Inn, 963 Friends Lake Rd, Chestertown, NY  (518) 494-4751

Getting to the Tour Start (Chestertown, NY/Saratoga Springs, NY):

Driving:  Approximate travel distance to Saratoga Springs, NY--

  • Albany, NY:  35 miles
  • Binghamton, NY:  163 miles
  • Boston, MA:  199 miles
  • Burlington, VT:  116 miles
  • Newark, NY:  180 miles
  • Rochester, NY:  220 miles

Albany International Airport (ALB) is served by Air Canada, AirTran, American, Cape Air, Delta, Southwest and United.

Ground Transit:   
A courtesy shuttle will be provided on the morning of Day 1 to Friends Lake Inn from both the Albany Airport Area and Saratoga Springs.  The pickup times are 8:30-9:00 a.m. in the Albany Airport area and  9:45 in Saratoga Springs. 

Parking:  We have arranged for long term parking there for the duration of your tour.  We will end the tour at the same inn with an opportunity to shower there prior to departure.  

Arrival/Departure Timing: 

Arrival time at Friends Lake Inn on the first day of the tour is 11:30 a.m. if renting equipment from us, or 12:30 p.m. if bringing your own bike.  Guests will want to meet us at these times dressed in bike clothes, or ready to change into them.  If you are planning to leave your car in Saratoga Springs and shuttle with us from there, the time for that is 10:00 a.m.

We plan to wrap up around 2:00 p.m. on the last day in Saratoga Springs.  Shuttles will be available back to Friends Lake if you left your car there, and to the Albany Airport.  Your return flight should be no earlier than 5:00 p.m. that evening.


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