Hudson Valley Bike Tour

Explore the Beauty of New York with our Hudson Valley Bike Tour

Our Hudson Valley bike tour is one you’ll never forget! Embark on a journey through the breathtaking Hudson Valley in New York, where the rolling hills, tree-lined roads, and picturesque farm roads offer some of the most spectacular biking in the greater Northeast region. Discover the perfect blend of challenge and leisure as you pedal through challenging hills and smooth flats, taking in the rich history and stunning vineyards along the way. Relax by the river or explore the grand estates of Eleanor Roosevelt, Val-Kil, and the Vanderbilt estate. The trip culminates in two delightful stays in the charming towns of Hudson and Rhinebeck, where the farm-to-table culture is in full bloom. Experience the beauty and diversity of the Hudson Valley and create memories that will last a lifetime.

  • 6 Day Adventure
  • July 23rd – 28th – $3,595  (SOLD OUT)
  • September 10th – 15th – $3,595
A cycling at a vineyard on a Great Freedom Adventure Hudson Valley bike tour.

Scenic Cycling and Luxurious Amenities throughout Hudson Valley

Great Freedom Adventures prides itself on providing the most unique cycling experiences in the most scenic parts of New England. Our Hudson Valley bike tour is one of our signature trips. With iconic historic lodging and exceptional cuisine to accentuate your tour, this trip will be on you never forget. Every cyclist who loves bikes tours, whether just starting to travel or seasoned explorers, will love this trip through the valley!


  • 6 days of bicycling
  • Bicycle and helmet rental
  • 5 nights lodging
  • 5 breakfasts
  • 2 dinners
  • 2 lunches
  • 2 dedicated guides
  • Van support
  • Daily snacks and cold drinks
  • Maps and cue sheets for each day’s ride
  • Luggage transport
  • Welcome refreshments
  • Guided kayak adventure
  • Daily cold drinks and snacks
  • Maps and cue sheets for each day’s ride
  • 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


Inclusions and Amenities

All Inclusions and amenities are subject to change, should we change our stay or dinner options, comparable options will be provided. 

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

Rider Level


Lodging Options

Standard Room at Various Hotels and Inns

Max Occupancy: 2 Guests

Single supliment available

Throughout the tour, guests will stay in a selection of upscale Inns and Hotels along the way. As many are Historic Inns, rooms may vary in design, aesthetics, and layout. We’ve provided some sample images to give you a sense of what your accommodations may look like. Please note in the room selection process; we ask that you choose between a shared or double occupancy room and a private room for individual guests.



Meals Included

Private Rooms



We start the journey in Hudson, New York. Long term parking is available behind our hotel in Hudson.



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


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:

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

Booking Information


7 days prior to the adventure departure.


A deposit is due upon booking – $750 per person for five to eight day tours and $500 per person for three to four day tours. Payments may be made by check or credit card. Our receipt of the deposit, registration form, and signed Release form will secure your reservation.

An invoice for the balance will be emailed and final payment is due no later than 30 days (exceptions made for last minute booking) before the tour departure date. Payment may be made by check or online with a credit card. If final payment is not received by the due date, Great Freedom Adventures reserves the right to cancel the reservation.


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.)


Travel insurance is available from a number of insurers or their representatives, such as CSA Travel Protection or Travel Guard. You may compare prices and policies at Insure My Trip. We do not sell insurance or recommend any particular insurer or policy, but we highly recommend that you obtain travel insurance.