After a year of planning and anticipation, we recently crossed off an event on our bucket list and rode the 5 Boro Bike Tour in New York City. This ride, or as I heard it called by someone on their Facebook Group page, is more of a unique spectacle than anything else. Yes, it’s definitely a ride, and at 40 miles, it could be a challenge for less experienced riders. With 32,000 participants, it takes on a life of its own as riders roll through the city streets in a slow, steady stream. The streets are car-free on this first Sunday in May and it is definitely an epic journey.

We opted for the VIP entry after speaking with several past participants. In addition to the swag like a tour jersey, bike bag, and other goodies, one of the most important amenities of the extra fee was a guaranteed start in the first wave. Trust me, if you are going to ride with 32,000 other riders, you definitely want to start in the first group. Rumor has it that later waves get bottle necked and there is much walking. Not really how we wanted to spend the day, so we forked over the dough and opted for VIP.

We rented our bikes from Unlimited Bikes and had no issues at all when picking them up bright and early Sunday morning. The line was long, but it moved pretty quickly. Then we meandered over to the starting line, following other cyclists since we didn’t really know where we were going. The atmosphere was electric, everyone was so excited and so were we.

Our experiences at RAGBRAI really helped with handling the large crowd, we were used to riding in large groups and knew how important it is to hold your line and be aware of everyone around you. We had anticipated stopping for libations along the route, but quickly were swept up in the ride itself and stopping along the way seemed a little less enticing. We did, however, opt for a quick stop at a local coffee shop to help take the chill off the morning. And we did stop at two of the rest stops, not so much for food or restrooms, but more to be a part of the whole experience. The number of bananas available was astounding, I later heard that Del Monte donated 50,000 of the fruit to the ride!

Even though we were not completely familiar with the roads and bridges in New York, it was easy to see that riding on car-free roads was a huge deal. The Queensboro Bridge is a spectacular structure that was amazing to see up close and personal. Pedaling on the Brooklyn-Queens Expressway was equally impressive as we imagined what it must be like packed with cars. The high point for me was the ride over the Verrazano Bridge, and I will admit, it had alot to do with the fact that we watched Saturday Night Fever a week before we left for the trip. I couldn’t help but think about the scene with John Travolta and Karen Lynn Gorney as they sat on a bench in the shadow of the longest suspension bridge in the US contemplating life outside of Brooklyn.

As we arrived on Staten Island, we knew our adventure was coming to a close, and we really didn’t want it to end. It was a chilly day and I wished I had put on an additional layer of clothes, but I wanted to keep riding and take in the great city in my favorite way…on two wheels. Alternatively, there were 40th anniversary commemorative medals and a VIP gourmet lunch waiting for us, so we parked the bikes and joined in the festival finish.

With little knowledge of what would be served at this VIP lunch, we were pleasantly surprised with some of the best salmon we have ever eaten. Mind you, the caterer was feeding several thousand riders, and the location was a park on Staten Island. The last few times I have ordered fish at Florida restaurants it has come out way overcooked and rubbery. Pretty cool that New Yorkers can prepare it perfectly.

On our way to the ferry to get back to Manhattan, we noticed a small bar with many bikes parked out front. In true RAGBRAI fashion we stopped (it was the first bar on the left, after all), parked our bikes and joined the other cyclists for a post-ride beer. Sitting at the front of the bar it was warm, cozy, and fun to watch the other cyclists ride by on their way to the ferry. Some stopped to join us, many looked longingly at the bar evidently wanting to stop, but talking themselves out of it. Too bad, because it was the perfect finish to a great day of riding.

As always, I thought about some take-aways for this adventure:

  1. I highly recommend the VIP experience for this tour. It’s expensive, but worth it to start in the first wave. And the other perks are good, too.
  2. If renting a bike for the ride, pick it up the day before if possible. It would have been nice to just roll to the start of the ride and not have the challenge of getting to the bike pick-up area.
  3. Pick accommodations in lower Manhattan. Getting from our AirBnB in Brooklyn to the bike pick up took nearly an hour, not the 35 minutes we expected. Having a hotel convenient to the starting line would be a nice start and end to the day.
  4. Overdress for the weather. Seriously, I’m not sure what I was thinking when I decided that low 50’s and partial sun could be warm on a bike. Not so much.


With a few adjustments to our plan, we just may be in NYC for the 5 boro bike tour in 2018!