Fall classic: Westchester’s premiere bicycling event is back

The Golden Apple/Dirty Apple, Westchester Cycle Club’s premiere event, returns on Sunday, October 12, 2025, perfectly timed to experience the beauty of autumn’s peak colors while cycling the county’s scenic back roads.

The WCC is marking its golden anniversary this year, and the all-volunteer club is gearing up for an event to remember. Rides start at Lewisboro Town Park in South Salem, NY, and roll through the charming, historic towns of Bedford, North Salem and Pound Ridge.

Whether you’re a road cyclist or want to go off-road The Golden Apple/Dirty Apple has a route for you. These specially created, self-guided routes take in quiet country roads, farms, reservoirs and expansive views of the landscape.

Road routes cover 25. 40 and 62 miles, with the option to ride a century or double metric. Gravel routes stretch 25 and 40 miles, with the option to make it a gravel metric century (62 mile) ride.

Fully supported rest stops are provided for the longer rides. All participants enjoy a box lunch afterward. “SAG” wagons and mechanical support are available.

The towns of Bedford and Lewisboro are home to more than 40 miles of unpaved roads, popular among riders who seek the challenge of The Dirty Apple’s off-the-beaten pathways featuring everything from smooth hardpack to gnarly gravel.

“It’s a great event that promotes cycling,” event chair Judi Tota said. “You’re getting so much when you go on a bike ride. You’re getting exercise, fresh air, sunshine, and you get socialization and community and camaraderie.”

Vedat Gashi, chairman of the Westchester County Board of Legislators, said he’s looking forward to the event this autumn.

“Northern Westchester's rolling hills, picturesque lakes and quiet country roads create the ideal backdrop for fall cycling,” Gashi said. “The Golden Apple and Dirty Apple rides in October offer both residents and visitors a unique opportunity to explore our district's stunning landscape during peak foliage season. I’m excited to join the fun this year and hope to see you there.”

Spots are limited and spots are filling up fast. Signup is by advanced registration only — there will be no day-of-event admission. August pricing is $40 for club members; $55 for non-members. September pricing is $45 for members and $55 for non-members. In October, the costs are $50 for members and $65 for non-members. Last registration date is Friday, Oct. 10. Visit westchestercycleclub.org/GADA to register.

Founded in 1975, the nonprofit Westchester Cycle Club promotes community awareness and enjoyment of cycling through events, tours, lectures, demonstrations and other activities for members and the public.

The club, with some 600 members from across the county and beyond, welcomes riders of various ages and skill levels. The WCC was designated the top bicycling club in the country in 2011 by the League of American Bicyclists.

Experience Autumn's Beauty on Two Wheels 

• Who: Westchester Cycle Club
• What: Golden Apple/Dirty Apple, with road and gravel rides ranging from 25 to 62 miles and longer; post-ride lunch for all
• When: Sunday, Oct. 12, 2025
• Where: Lewisboro Town Park, South Salem, NY
• Details: westchestercycleclub.org

Robert Brum is a freelance journalist who writes about the Hudson Valley. Contact him and read his work at robertbrum.com.