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Adirondacks & Vermont Bicycle Tour 
A bicycling vacation of New York's Southern Adirondacks and Southwest Vermont 


Day 1 l Day 2 l Day 3 l Day 4 l Day 5 l Day 6 l Lodging l Getting There l Cycling  

Area of the Adirondacks and Vermont Bicycle Tour 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.

(**Note:  Itinerary Details are subject to change)

Tour Fast Facts:
Highlights Dates: Price:
6 days / 5 nights

Beautiful Adirondack 
lake views,

 Vibrant Saratoga Springs,

Charming Vermont towns,

elegant lodging and 
gourmet cuisine. 



2018 Dates:

June 17 - 22

June 24 - 29

(All are Sun. - Fri.)

Opt in for email date 
announcements here:



2018 Price:
$ 2245 - 2345 / person

Price range reflects 
early to late enrollment.  

Bike rental: $100
Single occupancy 
room supplement: $500

Tour prices subject to change

Dates with an asterisk * have a solo traveler hoping for a roommate--  Call for details
RESERVE YOUR SPOT (click here)  

Day 1:  

Meet the group in Saratoga Springs.  Quickly we will be on country roads leading into the Adirondacks.  Valley roads and a few short climbs will take us by babbling streams 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.   

Bicycling Distance:   42 miles inn to inn, rolling hills with a few longer climbs.  Additional miles available if desired.

Day 2:   

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.

Bicycling Distance:  65 miles inn to inn,  rolling hills with a few longer climbs

Day 3: 

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.   

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

Bicycling Distance:  40 - 75  miles, rolling hills with a few longer climbs

Day 4:  

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.  You'll reach the upscale tourist town of Manchester in time to explore retail opportunities and museums.  Dinner is included at a restaurant nearby.

Bicycling Distance:   56 miles inn to inn, rolling hills with a few longer climbs

Day 5:  

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 back to Saratoga Springs.  

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

Bicycling Distance:  46 miles inn to inn, rolling hills with a few longer climbs.  More descending that ascending!

Day 6: 

Wake up in the town of Saratoga Springs, NY.  Famous for the horse racing tracks located nearby, Saratoga Springs is packed with trendy shops and upscale restaurants.  

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.

Bicycling Distance:   35 - 40 miles, rolling hills with a few longer climbs


Night 1: 

Friends Lake Inn, 963 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.  2014 TripAdvisor Certificate of Excellence winner.

Night 2 & 3: 

Lilac Inn, 53 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.

Nights 4:  

The Inn at Manchester, 3967 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.

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.  

Extend Your Vacation:   

There is a lot to do in and around nearby Saratoga Springs if you have time.  Of course the historic Saratoga Race Course is the main attraction each summer.  We are intentionally avoiding that season, which starts a couple of weeks later.  There are plenty of other things to keep you busy here:  a vibrant shopping and dining district, historic sites, hiking trails and more.


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


Driving:  Approximate driving distances to Saratoga Springs:

Albany, NY:
35 miles
Binghamton, NY:
163 miles
Boston, MA:
199 miles
Burlington, VT:
116 miles
Newark, NJ:
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:   
Taxi, limo, and shared sedan service is available to and from the airport.
We recommend Saratoga Hybrid Cab:  (518) 698-4122. 

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.


Call 888.251.3206 (local number is 336.794.1054) or click here to make your reservation today!

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Carolina Tailwinds   P.O. Box 24716   Winston-Salem, NC 27114-4716   888.251.3206 or 336.794.1054