Bike the Berkshires

Upper West Side
Upper West Side
Broadway and West 76th Street
to 6:30PM
8:00AM to 6:30PM
Arrive by 7:45AM
26.0 miles
800 feet
elevation gain

This trip is currently unavailable.
About the trip


  • See the Shawangunks in a new way
  • Visit a hidden pizza cafe

  • See the Wallkill river from the Rosendale Trestle

  • Ride on the historic rail trail


Spend the day riding through one of Upstate New York's most scenic areas. After departing the city, you'll quickly be transported to the heart of the Hudson Valley. Your bikes will be waiting for you at the launching point near the Wallkill River. From here, your guides will take you for a relaxing ride along the Wallkill Valley Rail Trail (a favorite of New York cyclists). There will be plenty of chances for photos as you bike over the river and in the shadow of the Shawangunk Ridge. The day will be full of stops to take in the views and to enjoy the shops and cafes of historic area. Some highlights of the day may include a trip over the Rosendale Trestle and a stop at a hidden woods cafe. After a day of exploration and relaxation, we'll return our bikes and head back home.

This trip is appropriate for cyclists of all levels.

Share Trip
Level 4/10
800 feet elevation gain
26.0 miles
Upper West SideBroadway and West 76th Street
8:00AM to 6:30PMArrive by 7:45AM

Pack List

  • Your lunch or money to purchase lunch in town
  • Ample snacks
  • At least two liters of water
  • A backpack. Need a recommendation? Check out Deuter!
  • Weather-appropriate clothing. For a great selection and discounts, check out our partners.
  • Camera
  • Cash for shopping
  • Comfortable athletic clothing
  • Sturdy sneakers
  • Hat
  • Jacket
  • Sunscreen
  • Expert guides
  • Transportation
  • Park permits
  • Bike and Helmet Rental

Drive to Meet Option

If you would prefer to drive yourself, you can select the "drive to meet" option at check out.  You'll meet your guide at Sojourner Truth Park on Plains Road in New Paltz, NY at 9:30 AM. 

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