David Whitehead Ride to Greenwich, CT

  • July 19, 2026
  • 7:30 AM
  • Grand Concourse, Bronx

David Whitehead’s Greenwich Challenge: Hilly, Scenic & Epic

Ready to test your legs and soak in some incredible coastal views? Join David Whitehead for an epic trek out to Greenwich, Connecticut. This is a challenging, hilly route designed for riders looking to push their limits, earn their elevation, and enjoy some beautiful scenery along the way.

Because of the distance and the demanding terrain, we are getting an early jump on the day. No sleeping in for this one!

  • Meet Up: 7:30 AM

  • Wheels Down: 8:00 AM (Sharp!)

  • Meeting Location: Grand Concourse, The Bronx

  • The Distance: Flexible! The exact mileage and final loop will depend on who shows up and what the group's appetite is for extra bonus miles. Come prepared for a long, solid day in the saddle.

  • The Terrain: Hilly and demanding. You will definitely need your climbing gears for this one, but the stunning views over Connecticut are worth every pedal stroke.

  • No Rider Left Behind (On the Climbs): While the hills will naturally split things up, this is a community effort. Everyone will regroup at the top of the major climbs, so you can tackle the ascents at your own pace without fear of getting dropped.

Pack plenty of nutrition, check your tire pressure, and bring your climbing legs. Let's conquer the hills to Greenwich!

FUN FACTThe Grand Concourse is a major 5.2-mile boulevard in the Bronx, running from East 138th Street to Mosholu Parkway. Inspired by the Champs-Élysées in Paris, it features the largest concentration of Art Deco architecture outside of Miami and is a highly recognizable geographic spine of the borough!



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