New York Bike Tour - Autumn Along The Hudson


Available Tour Dates:

October 4 to October 9, 2020


Bike amidst the yellow, orange and red hues of autumn. Pedal on traffic-free country roads past immaculate horse and cattle farms. Bike the new Walkway over the Hudson, the longest pedestrian and bike bridge in the world. Visit historic houses along the Hudson including those of Franklin and Eleanor Roosevelt, the Vanderbilt family, and Olana, the incredible home of Frederick Church. Marvel at the Frank Gehry building at Bard College. Stay in historic country inns and enjoy delicious meals at great local restaurants.  Experience and enjoy some Hudson Valley hospitality.

Tour Level:  Moderate

New York Bike Tour:  Hudson Valley Historic Houses and Fall Foliage


  • Bike on peaceful country roads amidst the spender of magnificent fall foliage
  • See and bike the longest pedestrian bridge in the world
  • Visit "Springwood" the magnificent historic estate of FDR on the banks of the Hudson
  • Bike to the hilltop estate "Olana," home of famous landscape artist Fredrick Church
  • Visit historic country villages such as Rhinebeck, Germantown, Copake, Millerton and Kinderhook
  • Stay in lovely inns and hotels and dine at great local restaurants


Terrain: Generally hilly with areas of more gently rolling terrain. The tour has been designed for low or high mileage and to bypass more significant hills making the trip comfortable for bikers of differing abilities.

Weather: The average high temperature in the area this time of year is 62° F and the low is 40° F.


New York Bike Tour: Hudson Valley Historic Houses and Fall Foliage

Price: $1995

Included in Price:

• 5 nights accommodations in unique inns and B&Bs

• All breakfasts, 4 dinners, and snacks along the way

• Entrance fees for Springwood in Hyde Park, FDR's riverside estate

• Entrance fees to Olana, the hilltop home of landscape artist Frederic Church

• Experienced guides familiar with the local area

• SAG (Support and Gear) Van to provide baggage relocation, mechanical support, snacks, fresh water, and
"rest rides" as needed

• Cue sheets and maps with daily meetings to review route options and points of interest

Additional Fees:

• Single Supplement: $450 (room mates will be sought when requested).

• Bike Rental: $150 for hybrid bikes - $250 for road bikes.


New York Bike Tour:  Hudson Valley Historic Houses and Fall Foliage

Beekman Arms:  America's longest continuously operating inn, the Beekman Arms first welcomed guests in the 1700's and offers today's guests charming  accommodations, pleasantly old fashioned, yet unobtrusively modern.  Steeped in history and a tradition of service, the Beekman Arms offers guests a unique experience during their visit. You can visit their web page by clicking here .

St. Charles Hotel:  Over 139 years of charm and history greet you at this fine hotel.   The St. Charles is nestled in the historic town of Hudson, New York.  Warren Street with its abundance of antique shops, galleries, and specialty stores is just a short walk from the lobby.   You can visit their web page by clicking here 

Wake Robin Inn:  The Wake Robin Inn opened its doors in 1899 as a different kind of Lakeville landmark, The Taconic School for Girls.  Fifteen years later, it became an Inn.  Offering unique accomodations on a hilltop location, The Wake Robin is the destination for those seeking graceful lodging in the Connecticut Berkshires.  You can visit their web page by clicking here.

New York Bike Tour:  Hudson Valley Historic Houses and Fall Foliage


Arrival and Departure: The tour will originate and terminate in Rhinebeck, NY.  Escapades will assist with hotel arrangements and local transportation both before and after the trip. 


Daily Mileage Options:  28-40 mile daily base routes with longer and shorter options available according to individual preferences.


Day 1: Rhinebeck
The tour begins in Rhinebeck.  We will meet in the lobby of the historic Beekman Arms at 4:00 pm, fit the rental bikes, and take a short ride around Rhinebeck. We will then meet in the library of the Inn at 6:30 pm for cocktails and introductions, followed by dinner at the Beekman Arms Inn.
Lodging:  Beekman Arms Inn
Meals: Dinner


Day 2: Rhinebeck to Hyde Park, Historic Houses and Walkway over the Hudson
Today we bike to the Walkway/Bikeway over the Hudson in Poughkeepsie, the longest pedestrian bridge in the world. After soaking in the view from the bridge, we visit Hyde Park and tour Springwood, the riverside home of Franklin Roosevelt. Bikers may also visit the Vanderbilt and Mills mansions along the way. Those wanting to ride longer can enjoy the scenic trip to Schultzville and Clinton Corners, home of Clinton Winery that provided the wine for Bill Clinton's inaugurations.
Lodging:  Beekman Arms Inn
Meals: Breakfast and Dinner


Day 3: Rhinebeck to Hudson
We will ride north along River Road through Bard College with optional visits to the Clermont Estate, Montgomery House and the Frank Gehry building at Bard. We will continue on country roads to the old towns of Tivoli, where there is a good bakery, and Germantown, both great lunch spots. We then bike north on quiet roads to Olana, home of the famous Hudson River painter, Frederick Church, and the small city of Hudson. This historic town was once a vibrant center of shipping and whaling and is filled with architectural gems. Now a major antiques center, there are many shops and art galleries lining the main street. We stay at the St. Charles Hotel.
Lodging:  St. Charles Hotel
Meals: Breakfast


Day 4: Hudson Loop North to Chatham
As we start our day we leave Hudson to ride through farmland, cornfields, and orchards, stopping to view the outdoor sculpture park at Omi International Arts center.  After touring the outdoor sculptures at Omi, our ride passes through gracious 18th and 19th century hamlets to arrive in Old Chatham, a wealthy rural area graced with stone walls, wonderful old cemeteries, and white churches.  During our visit we check out the Old Chatham Sheepherding Company, the largest sheep dairy farm in the country offering handcrafted artisan sheep's milk cheeses and yogurts . We follow our farm visit a stop at the charming old General Store in the village. Afterward, we ride to historic Kinderhook, the home of former President Martin Van Buren. We complete our Hudson Loop with a pedal along the Hudson River, past nature preserves and river views, returning back to our lodgings in Hudson.
Lodging:  St. Charles Hotel
Meals: Breakfast and Dinner


Day 5: Hudson to Lakeville
Today we bike out from Hudson past beautifully preserved old barns, the long black fences of horse farms, and rolling hills dotted with fall color. We will bike to Copake Falls where we can see the Copake Iron Works or hike to beautiful Bash Bish Falls. Our next leg on the trip to Lakevile takes us along a quiet tree-lined bike path and then on to Lakeville and our lodgings.  We will stay at  the Wake Robin Inn.
Lodging:  Wake Robin Inn
Meals: Breakfast and Dinner


Day 6: Lakeville to Rhinebeck
After breakfast at the Inn, we will ride through horse farm country as we make our way back to Rhinebeck.   Our tour will officially end in Rhinebeck and we will bid our fellow bikers farewell.  Changing rooms and showers will be available at the end of the ride.  Escapades will transfer guests back to the Beekman Arms in Rhinebeck, local rental car locations or the Rhinecliff train station for Departures.
Meals: Breakfast

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