NY Hudson Valley Bike Tour

6 Day Adventure




  • Street Biking
  • Wellness


  • Intermediate
  • Expert









  • 6 days of bicycling
  • Bicycle and helmet rental
  • 5 nights lodging
  • 5 breakfasts
  • 3 dinners
  • 2 lunches
  • Narrated River Cruise with wine or beer
  • 2 dedicated guides
  • Van support
  • Daily snacks and cold drinks
  • Maps and cue sheets for each day’s ride
  • Luggage transport
  • Admission to: Olana
  • The Vanderbilt Mansion
  • Springwood, FDR’s home
  • FDR Museum
  • Poet’s Walk
  • Vineyard tours and wine tastings
  • Walk gardens and grounds at historic estates
  • Tax and gratuities for meals and side excursions
  • Transport from/to the Albany Airport or Hudson Train Station
  • Featherweight, high visibility, reflective mesh vest
  • Water bottle

Packing List

  • 2 pairs of bike shorts so you can alternate every day
  • 1 pair of quick dry pants for cycling
  • 2-3 pairs of biking socks + 1 pair of waterproof socks
  • Bike shoes
  • 2 quick dry cycling jerseys + one long-sleeved jersey if the weather is colder
  • Arm warmers, leg warmers
  • Rain gear, including a helmet cover, shoe covers, pants, and jacket
  • Cycling gloves
  • Sunglasses
  • Bandana

Lodging Options




Meals Included

Private Rooms



We start the journey in Hudson, New York. 

Day 1:

Enjoy a welcome lunch in Hudson, NY. Walk through the planned landscape of paths, carriage roads, and gardens with sweeping views of the Hudson River. Ride to Olana, Frederic, and Isabel Church’s hilltop architectural masterpiece. Tour the mansion, and view exquisite Hudson River School artwork. Bike back to Hudson and explore the town’s varied architectural styles, shops filled with antiques, home furnishings, fine artwork, beautiful fashions, and more. Enjoy dinner at a top Hudson restaurant.

Biking Mileage: 14

Day 2:

Pedal through a spirit-calming landscape of pastoral farmland, quaint villages, and country lanes shaded by majestic maples. Visit an intriguing place with giant outdoor sculptures. Riders choosing the long option can ride through Old Chatham, a charming historic village. Return to the inn, then explore the Hudson River from the water while enjoying a narrated cruise with local wine or beer offered by your guides. Cruise past a historic lighthouse and scenic islands with views of the majestic Catskill Mountains. With luck, perhaps see one of the resident bald eagles. For dinner, choose among many excellent options, from restaurants offering fine dining with world-class chefs to those with excellent casual food and live music.

Biking Mileage: 36 or 55

Day 3:

The Hudson Valley bike tour continues along the river to the impressive Clermont Estate, home to seven generations of Livingston’s. Continue to Bard College and view architect Frank Gehry’s eye-popping performing arts center. Pedal to Montgomery Place, Livingston’s meticulously preserved country estate. Stroll through sprawling gardens, lawns, and woodlands to find views of the Hudson and Catskills that are unforgettable. Stop for a rejuvenating hike at Poet’s Walk to enjoy sparkling views high above the river. Arrive in Rhinebeck, a historic and sophisticated little town known for upscale shops, excellent restaurants, and visual and performing arts. Don’t miss the antique center in a historic barn right behind our inn! Enjoy dinner together at Rhinebeck’s top-rated restaurant owned by a world-renown chef.

Biking Mileage: 31

Day 4 and 5:

DAY 4 :
Bicycle through a landscape of stately horse farms, fragrant orchards, and lush vineyards. Enjoy lunch in picturesque Millbrook, then explore the town’s fine antique shops. Visit wineries set on hilltops offering wide valley and distant mountain views. Sample the award-winning vintages, some of which have graced White House tables. As travelers have done for about 240 years, return to the inn to relax. Dinner is on your own, with several good options a stroll away.

Biking Mileage: 26 or 44

DAY 5 :
Pedal along the Hudson, stopping at the opulent Wilderstein and Staatsburg mansions. Visit National Historic Sites, including Springwood, the home that held FDR’s heart and to which he always returned. The Vanderbilt Mansion is a genuinely remarkable monument to wealth. Explore the house’s formal gardens and, if you wish, walk along the bluffs above the river to Bard Rock. Eleanor Roosevelt’s retreat, Val-Kill, exudes a peacefulness that belies its role in shaping world history. Tonight, enjoy an excellent dinner at the famed Culinary Institute of America.

Biking Mileage: 23, 35 or 42

Day 6:

Complete this remarkable journey by cycling back to Hudson, through fertile farmland, and along ridgelines with views of the Catskill Mountains to the west. By the end of your Great Freedom Adventure through The Hudson Valley National Heritage Area, you will have experienced a wealth of natural beauty and cultural richness that few other tours can offer.

Biking Mileage: 29

Departure Instructions

Complete this remarkable journey by cycling back to Hudson, through fertile farmland and along ridgelines with views of the Catskill Mountains to the west.

Booking Information

7 days prior to the adventure


Full payment is due at time of booking.


A booking may be cancelled within 30 days of the reservation with no penalty. See more details below.
A change to a different tour in the same calendar year will be allowed up to 60 days before the original tour departure date if space permits. There is no charge for this. Changes within 60 days of the original tour departure date are subject to cancellation fees as outlined below. Changes/transfers do not apply to custom tours.
All cancellations must be submitted in writing; refunds will be based on the day we receive written notice. Please purchase trip cancellation/travel insurance because exceptions to our cancellation policy cannot be made for any reason, including personal emergencies, illness or injury, canceled or delayed flights or ground travel to the tour departure point, or weather. Refunds will not be made for a participant arriving late or departing early from a tour, or for a participant not using accommodations, meals, or other services offered as part of a tour.
Cancellation Fees Are as Follows (Per Person):
Cancel 30 days or less from booking date – No charge (Does not apply to custom or private tours or to US tours booked within 60 days of departure or overseas tours booked within 90 days of departure.)

91 or more days before trip – $150
61-90 days before trip – $750 or $500 (loss of deposit)
31-60 days before trip – 50% of trip price
30 or less days before trip – 100% of trip price (20% of your payment may be applied to another of our tours departing within one year of original tour start date.)
If a tour is postponed by GFA due to COVID-19, all payments made will be applied as a credit for travel by 12/31/23 less any applicable third-party fees and a $150 per person administrative fee.


Travel and medical insurance are not included in this package. We strongly recommend that you purchase insurance to cover personal injury, cancellation, or interruption for your experience. You will need to separately purchase any trip interruption insurance through an outside provider. This must be done shortly after making your reservation (some require insurance to be purchased within 15-20 days of initial trip deposit).
We also recommend that you carry insurance to cover the risk of injury while you are at your destination. If you are injured, you will be charged the ambulance expenses associated with your evacuation as well as any expenses related to your medical care. Medical and evacuation insurance will help to cover these costs.

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