Embark on a Six Day Southern Adirondack adventure and Vermont cycling tour. Experience the untamed beauty of the Adirondack wilderness, the rolling farmlands of Vermont, and the serene upper Hudson River Valley on this exhilarating cycling vacation. Our tour promises to delight cyclists with a diverse array of landscapes, charming small towns, and breathtaking vistas.
We did the Florida tour with a group of 16. The inns selected by Anne and Greg were a pleasant surprise as were the restaurants. Steve’s patience and guidance while biking was greatly appreciated. We have toured together before but this was the most supported experience we have had. Their bikes were excellent. I highly recommend scheduling with this company.
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Trip Overview
Price
Early bird discount: $2725 per person
Full price: $2825 per person
Bicycle rental : $100
Single room supplement: $650
Upcoming tour dates & status
For the 2025 season, no dates are currently scheduled. Groups of 8 or more are welcome to inquire about private or non-private options.
Meeting/Departure Point
Nearest Airport
ALB Albany International
Duration
6 days, 5 nights
Tour difficulty
Hilly terrain, with a few challenging climbs
Included
- Lodging:
5 nights at boutique inns and lakefront resorts. - Meals:
Dinner on nights 1, 2, 4 & 5; all lunches except 1; all breakfasts; snacks; and hors d’oeuvres most nights. - 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 conclude 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.
Group Size
Carolina Tailwinds maintains a guest to guide maximum ratio of 7:1 on all our tours
About your guide
Expert guides ready to show you the hidden wonders of each and every destination
What You’ll See & Do
Day 1
33–45 miles, hilly, with a few challenging climbs
Meet the group in either Saratoga Springs 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 back 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. Lovely back roads lead to the climb over Graphite Mountain, followed by a thrilling descent to sparkling Lake George. A few miles along the lake bring us to the charming New York village of Ticonderoga. We’ll enjoy a quick lunch in this town that produced the eponymous #2 pencils. Afterwards 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.
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 lakefront back roads, charming East Middlebury, and quaint Shoreham, before rolling back into lovely Brandon. Grab lunch and in ice cream cone on the town square before doing a little shopping in the unique shops there. Known as the “Art & Soul” Village of Vermont, it is the quintessential Vermont town: a vibrant, walkable center of art galleries, studios, and shops and restaurants. .
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 3 of them will be included in your route. Also along the way, you will pass through Vermont marble country. Vermont Marble has been exported all over the world and continues to be important to the local economy. Our mostly rural route will pass through tiny villages such as Proctor, Middlebury Springs and Pawlett. 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 the nearby rolling countryside. Along the way, we will pedal through 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.
What’s Included in Your Tour Price?
Tour prices are per person rates and include all of the following:
- Lodging costs (double occupancy rooms), including all taxes and fees
- All breakfasts and most lunches
- All dinners described in the tour itinerary (alcoholic beverages in restaurants are generally not included)
- Morning and afternoon snacks
- Route planning and detailed laminated cue cards daily
- Guide support along the route
- Van support along the route
- Luggage transfer
- Fees for all ferries, tolls for all highways and any park entrance or guided tour fees where noted
- Transportation back to starting point
- Costs for any special activities such as canoeing, kayaking, sailing or rafting where noted
- Carolina Tailwinds t-shirt or day bag, water bottles, complimentary digital photo files from your tour
- Gratuities for restaurants at included meals and gratuities for housekeepers at included lodging
Please note:
All lodging costs are based on double occupancy. The single room surcharge rates apply to single room occupants.
Single travelers who desire a roommate match will be paired with other tour guests of the same gender in a room with two beds, if available. If a match can’t be found for a single traveler, a single occupancy surcharge will be assessed. To find out if a roommate match is available, call us. We will be happy to put you on a waitlist for a match if one is not already available.
Single travelers may request a private room, subject to availability, and to the single room surcharge rate payable in full at the time of the reservation.
Transportation to the tour starting point, including airfare and any airport transfers, is not included in the tour price. We can assist you with making any airport transportation arrangements or advise you on the nearest and most convenient airport.
Alcoholic beverages at restaurants are not generally included . A separate beverage tab may be run for anyone who would like a drink with dinner. Settling this tab will be the responsibility of the individual participants.
Bicycle rental is available as an option (prices above). We have road touring bikes and hybrid bikes for your use and invite you to forego the hassle of transporting your bike to and from the starting point. Click here for more information on the equipment available for your use.
Want to know more about our policies, terms and conditions? Click here to review our deposit requirements, cancellation policy and more.
We will be happy to address any additional concerns or questions you may have.
Simply email us at our Contact Us page, or call us at 1-888-251-3206 (local number is 336.794.1054). Ready to make your reservation? Click here to reserve a spot online, or call us at 1-888-251-3206 (local number is 336.794.1054).
Travel Insurance: We strongly encourage you to consider travel insurance. You may research and compare competing travel insurance policies at websites such as www.squaremouth.com.
Where You’ll Be Staying
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. TripAdvisor Certificate of Excellence winner.
Nights 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.
Night 4
Inn at Manchester, 3967 Main Street Manchester Village, VT 05254
An authentic Vermont country inn offering a secluded pool, homemade country breakfast, uniquely charming rooms, and a cozy pub. There are multiple spaces for relaxing after a great bike ride.
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, and flat screen televisions. A full cooked-to-order breakfast is served daily.
Get Prepared!
Cycling
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
Airports:
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.
Rental Bikes for Your Tour
Our Selection
Women’s Road Bike ⇒
⇐ Men’s Road Bike
Hybrid Bike Small ⇒
⇐ Hybrid Bike Large
Step Through Bike ⇒
Why Choose This Tour?
Experience the pleasure of crossing Lake Champlain on a cable ferry ride
Cycle through picturesque Vermont farmland and take in the tranquil beauty of the countryside
Explore charming towns like Ticonderoga and Brandon, providing perfect opportunities for memorable stops and photo ops along the way
Encounter local wildlife such as deer, birds, and more while enjoying the serene surroundings of lakes, forests, and babbling streams
Relax and unwind after a day of cycling on the patios, porches and gardens of four luxurious country inns
See What Our Customers Say About Us
Tailwinds offers routes that can vary from easy to challenging, but that are always scenic and engaging. The support on the road is absolutely best in class, the lodgings are always interesting, and the food is terrific. Best of all, the owners and guides personify “customer service.” Taking a Tailwinds tour is always the highlight of my cycling year. All of this at prices which are reasonable.
We just got back from a fantastic vacation with Carolina Tailwinds. They were super accommodating and fun. The trip had good variety including cycling, two boat rides, beach walk, kayaking, amazing food and happy hour every day. Every expectation was exceeded as they booked a private tour for my husband’s birthday bash. Equipment was fantastic and the guides were personal me and knowledgeable. Booking was easy and every detail was take. Care of. Thank you to the whole team.
We are two retired friends who left our non-cycling husbands at home to have a biking adventure. We throughly enjoyed our Florida tour…Anne and Greg attending to every detail…Although it seemed we were on our own, our guides were at our backs to provide snacks, sun screen, and any assistance needed…The bikers we rented from CT were fitted to us and were maintained in perfect condition…FIRST RATE! We’re ready to book another CT trip!
We have completed 4 trips with Anne and Greg and have another on reservation. Their attention to detail is evident throughout the tour but especially in the excellent route selection. Good riding is of course why most people go on a bike tour and we have never been disappointed with the miles they carefully select. Good food, nice accommodations, interesting off bike activities and leisurely happy hours all adds up to a relaxing vacation.
This company is awesome! I’ve been on several week long tours and this is by far the best company. My husband and I just completed our second tour with CT and every aspect was first class. The guides are attentive no matter what your skill level. We’re planning a third trip next year.!
…Having been on several other bike companies’ tours I have a good perspective to highly recommend Carolina Tailwinds…They were perfectly organized, personally knowledgeable of the routes, and prepared for everything we wanted or needed for a great week…All through the week CT added fine touches to our trip which you’ll just have to experience on your own CT tour. You’ll have an awesome week.
Excellent value. Routes, accommodations, food, activities, support, and equipment were all top notch. Superb attention to details big and small. I have toured with nearly a dozen companies. They were all good, but Carolina Tailwinds has been my favorite. You can spend more, but you won’t get more than you get from Anne and Greg.
The attention to detail and the readiness to accomodate requests from the riders separate Carolina Tailwinds from any other tour group that I have ridden with. One other feature that has to be mentioned is the standard of the accomodations and the food. They are both of the highest standard. The Carolina Tailwind tours are fun!
…The scenery was abolutely spectacular! Traffic was light and road conditions excellent. The routes were well-planned with detailed cue sheets that were easy to follow. The support we received from the CT team was first rate before, during and after each day’s ride. Accomodations were very good if not top of the line. The tour operators, Anne and Greg, are well-organized, friendly, and good companions on a ride. We will be repeat customers this Summer.
Carolina Tailwinds, hands down, is the best bicycle touring company anywhere. Their attention to detail and willingness to accommodate personal preferences are unsurpassed. Their routes are well-planned and the support and ability to deal with different riding levels…My wife and I have done nine tours with Carolina Tailwinds…We are veteran cyclists; if their tours were not really good, we would have never returned…we are going on our tenth this year.
We just signed up for our third tour with this excellent bike tour company. We fly from California just to go with Carolina Tailwinds. Their attention to every small detail is amazing. I think their personal attention as owners of the company is what makes the difference…really do care that each of their customers has the best possible biking vacation.
…The routes afforded beautiful scenery, and were well-supported…We especially liked the personal touch that Anne and Greg provided. They picked us up at our hotel; they kept a watchful eye on rider groups with a broad range of skills; and they hosted informal drinks and hors d’oeuvres each night before dinner…great exercise during the day and relaxing evenings with interesting people, comfortable lodging, and excellent meals.
Aside from knowing some of the most unique biking, lodging, and dining spots in the Mid-Atlantic area, Anne and Greg obviously love what they are doing…This husband and wife team is really tops when it comes to personal, friendly service and they excel in accommodating the needs of riders of all abilities…Our only complaint is that we never seem to lose any weight on their tours, but as they always remind us – “It’s a vacation, you’re not supposed to lose weight!” Looking forward to our fourth trip in four years with Carolina Tailwinds!
Trips are well planned and very well supported. The lodging chosen by the company suits the trips, are comfortable, and often unique. But the most notable item is the personal attention a rider receives throughout the trip. I’ve completed three trips with Carolina Tailwinds and have signed up for a fourth.
…‘Company’ is misleading: this is a personal experience…Count on excellent routing, craft-quality laminated and color-coded cue sheets, a daily pre-ride briefing, convenient and dependable sag support, and smaller, friendly groups. The clinchers for me, though, were the gourmet meals and the accommodations at small inns…I’ve been on 3 different trips with them now, and all cycling agendas have been represented and handled on each trip.
We love this company. We have toured with them three, going on four times and their attention to every detail and their organization skills keep us coming back for more. we have toured with three other companies, vbt, bike vermont, and pedal and sea adventures, and they surpass all of them. Food especially is excellent.
Carolina Tailwinds gives every attention to detail towards their customers. The routes they map out are clear and safe. The accommodations that Carolina Tailwinds select are 5 star all the way, from the lodging to the restaurants. The guides are friendly and accommodating to the cycling level of their guests. The size of the tour group are intentionally small to give the customer that undivided attention they deserve on their vacation.
We had used several bike tour companies and thought that they all did a good job. However, Carolina Tailwinds’ tours are operated by the owners of the company. Thus, their level of service exceeds that of other companies. We have now completed 5 tours with them and have another scheduled. Greg and Anne, the owners, are now like members of our family.
We are in our mid-seventies & have just re-discovered the joys of biking the past 3 years, biking over 2500 miles each of the last 2 seasons mostly hear in upstate NY. We’ve started the past 2 seasons with a Carolina Tailwinds tour & plan to do the same again this season. Anne & Greg just do a terrific job guaranteeing a wonderful vacation for us.
