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"I highly recommend a Great Freedom Adventure! A New England fall bike tour had been on my "bucket list" for years. My wife and I toured the Hudson Valley during peak leaf season with Great Freedom Adventures. All expectations were surpassed.

The amount of detail planning that had gone on behind the scene before we ever showed up was amazing. I was simply blown away by the meticulous planning that went into the itinerary, route design and the highly detailed cue sheets and maps. This detail allowed each rider to feel completely comfortable riding at their own pace. The guides were highly qualified and very helpful. The GFA sag wagon was always nearby, filled with goodies and ready to offer additional support if needed. The accommodations were excellent and our dinners were at outstanding restaurants, each one better than the last. It would be impossible for me to say which one I like the best.

The beauty and serenity of riding the quiet tree-lined roads, the changing leaves, the magnificent views overlooking the Hudson at Poet's Walk and the glimpses of the Catskills in the distance...made it impossible not to appreciate nature's beauty.  If it is possible for a "do over" on a "bucket list", like General McArthur - I shall return!"
Pruett B., GA

Hudson Valley NY Bike Tour: About the Trip

New York

New York Bike Tour in the Hudson Valley National Heritage Area

New York wine bike tours

Fabulous Bicycling on New York's Country Roads
We’ll let you in on a secret: the bicycling in New York’s mid and upper Hudson Valley is some of the best in the country. 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.

Wineries, Horse Farms and Fertile Farmland
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.

New York wine bike tours

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.

Exciting 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. 

new york bike tour

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.


Note:  This trip will appeal to groups traveling together who have a wide range of interests. Whether it’s a love of cycling, walking, history, architecture, museum visits, art, antiques, gardens, wineries, shopping or epicurean delights, you will find it here.  Our New York bike tour allows flexibility to focus on the things that you like.  Want to spend less time biking and more time shopping?  No problem.  Want to skip the mansion tours and see more of the countryside from your saddle?  That’s fine too.  Our van and guides are available to make sure your Hudson Valley vacation is fabulous.

For another trip, which like this New York bike tour, includes cultural and historical gems along with great bicycling, please see our New England bike tour on Massachusetts’s North Shore.

Hudson Valley NY Bike Tour Highlights

Note - The August departure is timed to coincide with the start of the annual Hudson Music Fest. Hudson is being called the next Music Mecca and the festival is a three-day celebration of music all over Hudson - in the restaurants, nightclubs, bars, galleries, tents up and down Warren Street, at the riverfront and in the parks. Guests on the August departure may wish to allow additional time in Hudson on the last day of the tour in order to enjoy the music.


new york bike tour

NY Bike and Wine 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
  • Visit Old Chatham Sheepherding Co., producer of award-winning artisanal cheese (with longer distance option)
  • 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

new york bike tour

new york wine bike tour

wine bike tour 2

wine bike tour


For this New York bike tour itinerary, please view the Hudson Valley bike tour itinerary page.

Dates and Prices:

For the tour details, dates and prices, please go the NY bicycle vacation details page.

Questions? Please contact us and we'll be happy to help.

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