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Rides and Events in the Hudson Valley
Below is a listing of various bicycle events and bicycle tours in the Hudson Valley. Because of the pandemic, many of these rides have been pushed back until later in the year and some have not yet been scheduled. We will update this list as we find out more. If you know of a ride that is not listed, please contact us and we will add it to the list!
EVERY WEEK!
Join the Keegan Army for it's weekly rail trail rides! Routes rotate
between Kingston-area trails and are approximately 12 miles long. Ride
at your own pace. Enjoy post-ride beverages and make some new friends!
Follow the Keegan Army on Facebook for route updates.
between Kingston-area trails and are approximately 12 miles long. Ride
at your own pace. Enjoy post-ride beverages and make some new friends!
Follow the Keegan Army on Facebook for route updates.
April
Empire State Trail Tour - April 26, 2025
An organized 35-mile ride on the Empire State Trail between Brewster and Poughkeepsie. Options to ride additional segments of the trail are availble. Ride connects to Metro-North.
An organized 35-mile ride on the Empire State Trail between Brewster and Poughkeepsie. Options to ride additional segments of the trail are availble. Ride connects to Metro-North.
Hudson Valley Craft Brewery Bike Tour - April 27, 2025
A 35-mile ride down a rail-trail, ending at Captain Lawrence Brewery. Picnic lunch and beer tasting included. Ride connects to Metro-North.
A 35-mile ride down a rail-trail, ending at Captain Lawrence Brewery. Picnic lunch and beer tasting included. Ride connects to Metro-North.
May
An organized 35-mile ride on the Empire State Trail between Brewster and Poughkeepsie. Options to ride additional segments of the trail are availble. Ride connects to Metro-North.
Hudson Valley Craft Brewery Bike Tour - May 18, 2025
A 35-mile ride down a rail-trail, ending at Captain Lawrence Brewery. Picnic lunch and beer tasting included. Ride connects to Metro-North.
Noah's Ride - Usually held in May
Annual bike ride for diabetes research at Freedom Park in LaGrange will feature choice of three loops: 60 mile, 40 mile and 20 mile. Afterwards enjoy a great lunch and have some fun!
Women-only bike race, based in Woodstock.
Three 35-mile loops starting and ending at Tony Williams Park in Highland. Do all three and ride 100 miles! Or do fewer and that's OK too.
June
BX3: Bike, BBQ and Behavioral Health - June 1, 2025
A 30-mile roundtrip, recreational ride leaving from Bikeway in
Montgomery, NY with proceeds supporting mental health in the Hudson
Valley.
Montgomery, NY with proceeds supporting mental health in the Hudson
Valley.
Empire State Trail Tour - June 14, 2025
An organized 35-mile ride on the Empire State Trail between Brewster and Poughkeepsie. Options to ride additional segments of the trail are availble. Ride connects to Metro-North.
An organized 35-mile ride on the Empire State Trail between Brewster and Poughkeepsie. Options to ride additional segments of the trail are availble. Ride connects to Metro-North.
A 35-mile ride down a rail-trail, ending at Captain Lawrence Brewery. Picnic lunch and beer tasting included. Ride connects to Metro-North.
Discover Hudson Valley Bike Ride - Usually held in June
One-day event ride, based out of Poughkeepsie with 5 different routes up to 100 miles.
A 400 mile bicycle journey along the Erie Canal. This ride takes place over 8 days and contains 40 to 60 miles of riding each day. The ride is approximately 650 riders.
One-day event ride put together by the Rockland Bicycling Club. 25, 40 and 65-mile options
Empire State Ride To End Cancer - July 26-August 2, 2025
Bike tour from NYC to Niagara Falls to raise money for cancer research.
August
Empire State Trail Tour - August 16, 2025
An organized 35-mile ride on the Empire State Trail between Brewster and Poughkeepsie. Options to ride additional segments of the trail are availble. Ride connects to Metro-North.
An organized 35-mile ride on the Empire State Trail between Brewster and Poughkeepsie. Options to ride additional segments of the trail are availble. Ride connects to Metro-North.
Hudson Valley Craft Brewery Bike Tour - August 17, 2025
A 35-mile ride down a rail-trail, ending at Captain Lawrence Brewery. Picnic lunch and beer tasting included. Ride connects to Metro-North.
Cycle the Hudson Valley - August 4-9, 2025
7-day, 200-mile tour from the Albany area to NYC which follows the Hudson River section of the Empire State Trail.
September
Escape New York - September 13, 2025
One-day event ride put on by the New York Cycle Club. Choose from 6 different routes, up to 125 miles in length!
Braking AIDS Ride - September 13-14, 2025
Three-day charity ride The first day will be from Saratoga to Albany, the second day is Albany to Fishkill, with the third day going from Fishkill to New York City. This is a charity bike ride that is fully supported and open to riders of all abilities.
Empire State Trail Tour - September 27, 2025
An organized 35-mile ride on the Empire State Trail between Brewster and Poughkeepsie. Options to ride additional segments of the trail are availble. Ride connects to Metro-North.
Hudson Valley Craft Brewery Bike Tour - September 28, 2025
A 35-mile ride down a rail-trail, ending at Captain Lawrence Brewery. Picnic lunch and beer tasting included. Ride connects to Metro-North.
An organized 35-mile ride on the Empire State Trail between Brewster and Poughkeepsie. Options to ride additional segments of the trail are availble. Ride connects to Metro-North.
Hudson Valley Craft Brewery Bike Tour - September 28, 2025
A 35-mile ride down a rail-trail, ending at Captain Lawrence Brewery. Picnic lunch and beer tasting included. Ride connects to Metro-North.
One-day, charity event ride based out of Kingston to raise money for the Benedictine Health Foundation’s Rosemary D. Gruner Memorial Cancer Fund. 12, 25 and 50 mile routes.
One-day event ride, based out of Kingtson with 6 different routes up to 50 miles with a BBQ after.
October
Empire State Trail Vacation Tour - October 9, 2025 through October 14, 2025
Ride the Empire State Trail between NYC and Saratoga Springs this October. Spectacular scenery, nice hotels, great food and excellent customer service. Flexible dates and itineraries
Empire State Trail Tour - October 25, 2025
An organized 35-mile ride on the Empire State Trail between Brewster and Poughkeepsie. Options to ride additional segments of the trail are availble. Ride connects to Metro-North.
An organized 35-mile ride on the Empire State Trail between Brewster and Poughkeepsie. Options to ride additional segments of the trail are availble. Ride connects to Metro-North.
Hudson Valley Craft Brewery Bike Tour - October 26, 2025
A 35-mile ride down a rail-trail, ending at Captain Lawrence Brewery. Picnic lunch and beer tasting included. Ride connects to Metro-North.
A 35-mile ride down a rail-trail, ending at Captain Lawrence Brewery. Picnic lunch and beer tasting included. Ride connects to Metro-North.
One-day event ride starting in downtown Yonkers with 12, 25 and 50-mile routes that explore New Yorks 3rd largest city. This ride also has the most breathtaking views of the Palisades and the majestic Hudson.
Westchester Cycle Club Dirty Apple - Usually held in October.
The Dirty Apple is a gravel grinder in Westchester County (yes, there are dirt roads in Westchester). Choose from 40, 50, or 63 miles of mixed 50/50 dirt and paved roads.
Westchester Cycle Club Golden Apple - Usually held in October.
The Golden Apple is a road ride event in Westechester County. Come see the best roads from two wheels! Choose from 35, 45, or 73 miles.
51 or 76 mile routes out of Dorset, VT on some of the best back roads in the country at one of the most beautiful times of the year to be on two wheels. Vehicle support, a fully stocked feed station as well as food, beer & live entertainment
Can't find a ride you want to do?
Check out www.biketourfinder.com