Bob's story: Five Boro Bike Tour

BaseCamp athlete Bob Cuccaro shared his experience at the 2026 Five Boro Bike Tour in New York.

For anyone wanting to do an event that is more like touring a city…the Five Boro Bike Tour is for you. It was a cold Sunday a.m. and very windy. My Seigla and my Zipps were trying to act like sails with the cross wind for a good part of the day.

The tour starts in lower Manhattan; if you ever attempt this ride, be very careful, and don't clip in right away. There are a lot of people who are riding casually and are swerving constantly. I signed up for VIP just to avoid the massive crowds starting. Being in the first few hundred made it easier to get to a nice position at the start.

Cruising up to Central Park, there was a bottleneck and a few crashes. Central Park was a lot of fun riding through, although my allergies are making me pay for it today. Ride through Queens and rest stop was nice, although bumpy. The Seigla and 57s handled every bump nicely, while I saw road bikes and their pilots whimper, especially on the short cobble section. Not a lot of climbing other than bridges, and the Verrazzano bridge was fun to try to get some VO2 segment in at the end. Food was very good for the VIP and charity riders.

If you ever have it on a ride list, I suggest not taking a road bike and being more comfortable on your gravel bike. Be patient and don't think of it as a race, but a sightseeing recovery ride. Total distance was approximately 40 miles for the tour and biking back to the car.