New Routes…New Challenges!

The Ride the Ridge Bike Challenge, an all-experience-levels cycling event hosted by the High Meadow School, will celebrate its 11th anniversary on June 3 and expects more than 400 participants. However, this year’s event features some surprises.

It’s a New Day!

The most major change in 2017 is that Ride the Ridge is being held on a Saturday for the first time. The past 10 Rides have been on Sundays. “Riders said they wanted to make a full weekend out of it,” said Paul Rakov, this year’s Ride the Ridge chairperson. “For centuries, people have come to our area of the Hudson Valley to relax, explore, dine and just experience all that is here. Throw in a challenging bike ride and that sounds like a great weekend escape to us.”

Route Changes

Veteran Ridge Riders will find that some of the routes have changed this year. Rakov says that road construction required the planning team rethink ride logistics. “A major bridge in High Falls is under repair so, we had to come up with creative solutions to the 80, 50 and 11-mile rides. Our first priority was safety while the second was still delivering a memorable experience for Riders.”

The Ride the Ridge Mission

Ride the Ridge raises funds for the High Meadow School’s “needs-based” tuition assistance program. Over the past 10 years, it has become a much-acclaimed annual event that brings together the local community and cycling enthusiasts from as far away as Florida and Maine. For several years, Bicycling Magazine named Ride the Ridge one of the country’s “Best Cycling Events for June.”  

With safety as a priority, all rides are well marked with printed signs, staffed by more than 100 volunteers, and accompanied by a SAG wagon in the event of blown tires or other issues. The High Meadow School serves as the start and finish with a huge party full of delicious food and beverages open to all riders and guests.

Ride the Ridge Routes for 2017

80-Mile Ridge to Reservoir Ride:  Introduced in 2016 for Ride the Ridge’s 10th anniversary, the 80-mile ride first challenges experts to climb the Shawangunk Ridge, famed for it’s world class rock climbing and tri-state views. After a rejuvenating descent, riders head out to the Ashokan Reservoir that features stunning views of the Catskill Mountains and then back to the High Meadow school.

50-mile Bud Clarke Memorial Shawangunk Ridge Ride: named after one of the event’s founding organizers, this Ride focuses on the ascent up the West Trapps of the Shawangunk Ridge towards Minnewaska State Park. Riders make their way past the Trapps cliffs as they head back to Stone Ridge along the Wallkill River.


30-mile Reservoir Ride. Rerouted in 2016, this new route takes intermediate riders out to the Ashokan Reservoir, a major water source for New York City. Efforts to summit a few steep climbs are rewarded with panoramic reservoir and mountain views…and possibly a bald eagle or two!

13-mile Scenic Ride:  A new route this year is a bit longer than the 11-miler of years pasts, this is a fun and challenging ride designed for intermediate riders. Great for the tweener/teenage/college-age set, cyclists meander through farmland with stunning views in an out-and-back route that is new this year. Must be comfortable riding on open roads with traffic for this new route.


5-Mile Family Ride: Parents and children will enjoy riding in pairs down Main Street and through the scenic back roads and neighborhoods of Stone Ridge. Cheers from the onlooking crowd will greet riders at the finish line, an experience any new rider is not likely to forget. Note: Safety is a priority so, each child must have his/her own adult rider companion. No exceptions.

Helmets are required for all rides, no exceptions. Pre-and-post-ride food and beverages are included in the registration fee along with an commemorative t-shirt.


Information and Web Site

The start time for the 80-mile and 50-mile ride is 7:00am and riders are asked to arrive 30 minutes early to ensure a prompt start. For other information, start times and registration, riders should visit, or connect with Ride the Ridge at