Hudson Valley, NY Bike Tour – Great Freedom Adventures
tour-item-template-default,single,single-tour-item,postid-3560,mkd-core-1.1.1,mkdf-social-login-1.1,mkdf-tours-1.3,voyage child theme-child-ver-1.0,voyage-ver-1.3,mkdf-smooth-scroll,mkdf-smooth-page-transitions,mkdf-ajax,mkdf-grid-1300,mkdf-blog-installed,mkdf-header-standard,mkdf-no-behavior,mkdf-default-mobile-header,mkdf-sticky-up-mobile-header,mkdf-dropdown-default,mkdf-light-header,mkdf-medium-title-text,wpb-js-composer js-comp-ver-6.6.0,vc_responsive

Hudson Valley, NY Bike Tour

Hudson Valley, NY Bike Tour

per person


Hudson Valley National Heritage Area NY Bike Tour

Upstate New York’s Hudson River Valley
We’ll let you in on a secret: the bicycling in New York’s mid and upper Hudson Valley is some of the best to be found anywhere. Recreational and avid cyclists alike treasure this network of quiet country roads offering views of open farm country, the distant Catskill Mountains and the wide Hudson River.  The landscape feels very much like that in nearby Vermont, but with gentler terrain. Join us in touring some of the most picturesque routes in the Hudson Valley.

World-Class Restaurants, Wineries, Horse Farms and Fertile Farmland
If you are a foodie, you will love this tour. The Hudson River Valley is known for restaurants owned by world-class chefs. At night, enjoy dinners at some of the region’s top restaurants. By day, travel through fertile countryside, past idyllic dairy and agricultural farms, traversing manicured fields where horses, sheep and alpaca roam. Pedal through orchards to hilltop vineyards with long-range views. Taste several of the region’s award-winning wines, some of which have graced White House dinners. Sample artisanal cheeses, fresh fruits and heirloom vegetables by day, and feast on gourmet dinners each night filled with food from the very farms we’ve cycled past and prepared by the region’s finest chefs.

Mansions and Gardens
The bike tour of New York’s Hudson Valley includes visits to preeminent historical sites as well. Ramble through stately mansions built for the Livingstons, Vanderbilts and Roosevelts. See formal gardens designed by some of America’s foremost landscape architects and stroll the grounds at these stunning riverfront estates. Walk to a bluff with sweeping views of the Hudson River and Catskill Mountains, a setting said to have inspired the writing of Washington Irving.

Ehudson-valley-ny-bike-tour-4xciting Towns
Explore funky, chic Hudson, home to 65 antique shops, stellar art galleries and world-class restaurants.  A walk down Hudson’s Warren Street, described as a “dictionary of American architectural design,” is like a walk down through the centuries as you near the river. Feel the palpable excitement of Hudson’s recent renaissance.

Historic Places
Casually elegant Rhinebeck, another stop on the New York bike tour, is a charming village listed on the National Register of Historic Places. Enjoy the beautiful architecture of the historic homes, period barns and carriage houses while walking to lovely shops and restaurants. Watch for old hitching posts and carriage stepping stones too.

Wine, Art, History and Superb Cycling
The ridges, valleys, and plateaus framing the Hudson River create a spectacular setting, one that inspired a whole new art movement – The Hudson River School of Art. Great Freedom Adventures’ bike tour of New York’s Hudson Valley National Heritage Area will immerse you in the beauty, history, art, wine and cuisine of this remarkable region.

Tour Highlights:

  • Stay at fine historic inns including the oldest continuously operating inn in the country
  • Gourmet dinners prepared by talented chefs with fresh, local produce
  • Dinner at the renowned Culinary Institute of America
  • Cycling on beautiful country roads past manicured horse farms, picturesque sheep, and agricultural farms, alongside centuries old stone walls
  • Vineyard tours and wine tastings
  • A scenic river cruise past a historic lighthouse
  • Visit to Olana, Frederic Church’s Persian masterpiece of architecture
  • Charming villages
  • Hike at Poet’s Walk, Washington Irving’s inspiration for “Rip Van Winkle” with spectacular views of the Hudson River and the Catskill Mountains
  • Visits to FDR’s Home and Museum, Eleanor Roosevelt’s tranquil Val-Kill, and the impressive Vanderbilt Mansion
  • Experience the ethereal light of a landscape that inspired a whole new art movement – the Hudson River School of Art
  • Explore the mansions, grounds, and gardens of Montgomery Place, Wilderstein, and Staatsburg at will
  • Immersion in a fragrant landscape of vineyards and orchards
  • Antique shops and art galleries galore
  • Historic architecture

Tour Reviews & Testimonials


    Day 1

    Great Freedom Adventures Hudson Valley NY Bike TourEnjoy a welcome lunch in Hudson, NY. Ride to Olana, Frederic and Isabel Church's hilltop architectural masterpiece. Tour the mansion, and view exquisite Hudson River School artwork. Walk through the planned landscape of paths, carriage roads and gardens with sweeping views of the Hudson River. Bike back to Hudson and explore the town's varied architectural styles, and shops filled with antiques, home furnishings, fine artwork, beautiful fashions and more. Enjoy dinner at a top Hudson restaurant. Cycling Mileage: 14

    Day 2

    hudson-valley-ny-bike-tour-11Pedal 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 and 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. Cycling Mileage: 36 or 55

    Day 3

    hudson-valley-ny-bike-tour-25-great-freedom-adventuresThe 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 be rewarded with 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 chef who is simply magnifique! Cycling Mileage: 31

    Day 4

    hudson-valley-ny-tour-2Bicycle 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 if you like. 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. Return to the inn to relax, as travelers have done for about 240 years. Dinner is on your own with several fine options a stroll away. Cycling Mileage: 26 or 44

    Day 5

    wine-bike-tour-great-freedom-adventuresPedal 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 truly remarkable monument to wealth. Explore the house, 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 it's role in shaping world history. Tonight, enjoy a superlative dinner at the renowned Culinary Institute of America. Cycling Mileage: 23, 35 or 42

    Day 6

    hudson-valley-ny-bike-tour-15-great-freedom-adventures_edited-2Complete 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. Cycling Mileage: 29   Please Contact Us for detailed itinerary and arrival and departure information.

    The Inn at 34, Hudson, NY - 2 NightsEnjoy spacious, beautifully decorated rooms at this centrally located inn, easy walking distance to everything in Hudson. Fabulous breakfasts use fresh ingredients grown in the inn gardens or by local farmers. The innkeepers are gracious and highly knowledgeable about area history. One of the innkeepers raced bikes, he’s a talented baker and he knows just what hungry cyclists need!

      Or: Hudson B & B, Hudson, NY - 2 Nights Hudson B & B is located in a classic Federal style home built in 1790. The interior is elegant with period antiques and architectural details. Rooms are bright, airy and feature luxurious white linens for a serene retreat. The full, made-to-order breakfasts are excellent.
      beekman-arms Beekman Arms,  Rhinebeck, NY  - 3 NightsThis Historic Hotel of America is the oldest continually operating inn in the country with beautiful rooms offering today's comforts. The colonial tavern welcomes travelers as it has for over 240 years and its restaurant is excellent. The inn is located in the center of town, walking distance to shops and restaurants.

    2022 Dates

    July 10-15  |  August 14-19  |  October 16-21

    2022 Prices (Good till 11/15/21)

    $3,295, per person based on double occupancy. Single Supplement $895.

    Trip Length

    6 days, 5 nights


    Hudson, NY

    Cycling Level

    Easy to Moderate

    Daily mileage

    14-38 (Longer options: 14-55)


    Flat sections as well as rolling hills. Some hills may be steep but they are generally short. Occasional sections of dirt road.

    Bikes: You may bring your own bike or use one of ours. GFA bikes are high quality, lightweight, available with either drop or straight handlebars and are equipped with computer, mirror, waterbottle, handlebar bag, map case and seat pack with essentials. What's Included:
    • 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 (for you and your treasures found along the way too)
    • 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
    • Gardens and grounds walks 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
    • Waterbottle
    Frequent Adventurers, GFA alumni, may deduct 5% from the tour price. Please contact us for youth and group rates. Custom dates and duration are available for groups of six or more. Please Contact Us for detailed itinerary and arrival and departure information.

    Be The First To Know About New Tours

    Be the first to get latest updates and information about new tours straight to your email inbox.