In a six-day tour, riding 35-45 miles per day, you can cover the length of the Hudson River Valley, hitting key sights, vistas, and attractions on both sides of the river. Total distance is approximately 200 miles. This suggested itinerary starts in the town of Hudson, in the Upper Hudson River Valley. Use your arrival day to get oriented, stock up on supplies, and check out your gear. Steiner’s Sports on Warren Street can see to all your last-minute needs. If you have extra time, take a warm-up ride over to Olana (12 miles) to tour Frederic Church’s historic estate. Book accommodations in or near the towns of Hudson, Kingston, Hyde Park, Garrison, and Nyack.
Day 1: Hudson to Kingston
Get an early start for the first ride of the week, which starts in Hudson (Columbia County) and finishes in Kingston (Ulster County). Along the way, stop to visit Montgomery Place and refuel in Rhinebeck. Cross the river at the Kingston-Rhinecliff Bridge. When you reach downtown Kingston, walk through the Stockade District, check in to your hotel, and then look to the Rondout Creek area for dinner.
Day 2: Kingston to Hyde Park
Ride along part of the Wallkill Valley Rail Trail and through the college town of New Paltz. Be sure to see the historical homes along Huguenot Street and stop at a winery or two. End the day by crossing the river on the Walkway Over the Hudson and looping back north to Hyde Park.
Day 3: Hyde Park Rest Day
Take a day off to visit FDR’s home and library, the Vanderbilt Estate, and the Culinary Institute of America. Or add an optional loop through the countryside and wineries of eastern Dutchess County instead.
Day 4: Hyde Park to Garrison
Fuel up for an action-packed ride through Poughkeepsie, Beacon, and Cold Spring. Optional side trips include the Dia:Beacon modern art museum and a paddle on the river from a launch near Cold Spring. Finish the day in Garrison (Putnam County).
Day 5: Garrison to Nyack
Ride across the Bear Mountain Bridge and head south over Storm King Mountain to West Point. Take a tour of the military academy, and have lunch at the Thayer Hotel. For more mileage, add an optional route through Bear Mountain State Park. Or get off the bike for a few hours to hike along a section of the Appalachian Trail. Overnight in Nyack or Piermont.
Day 6: Nyack to New York City
Finish the ride along the Hudson with a ride under the cliffs of the Palisades and end at the George Washington Bridge. Alternatively, cross the river at Nyack to explore Tarrytown and the Rockefeller Estate. From Tarrytown, you can catch Amtrak back to Hudson, or plot a new cycling route for the return trip, with stops in Peekskill, Red Hook, and Catskill, for example.