A couple of weeks ago I wrote about the days leading up to officially becoming a Trumpet Head when Bill and I joined our friends and approximately 32,000 other bikers for our first riding of the 40-Mile Bike NY Five Boro Bike Tour. Our friends were veterans – some riding for as many as twelve years – and their experiences made every aspect of the weekend so much easier for the two of us. Unfortunately, even their veteran status gave them zero control over the weather…

I left off of Part 1 with Bill and me heading to bed with an alarm set for 3 AM on Sunday, May 5th. The first thing I did upon awaking was check the weather to see if, miraculously, the weather forecast had changed. It had not…


Dressing for Success

We mulled over what to wear in the cold rain and agreed that layers would work best. My layers were a short sleeved jersey, a thin nylon shell, and bike shorts; all pretty much to be covered by a clear plastic poncho. I asked Bill to not let peer pressure cause me to change my mind at the last minute even though I took my heavier long sleeved jersey with me – just in case.

We headed outside with our bikes (my Salsa Journeyman and Bill’s Salsa Cutthroat) trying not to wake our hotel neighbors as we clumsily carried our bikes down the stairs and out the back door. Once at our car, Bill loaded our bikes and we drove around in search of our team where we found them loading their bikes under the protective cover at the main entrance.


The eight of us drove caravan-style in three cars to the Staten Island Ferry. We parked along the street about a half mile from the ferry and waited in our cars until Paul (aka Mr. Incredible) got his speakers and American flags attached to his bike. I watched as my other friends eventually piled out of the other two cars and in a hasty panic, I ripped off my short sleeved jersey and put on my heavier long sleeved version. I layered my nylon shell and poncho back on top; and covered my hands with rubber kitchen gloves under my fingerless biking gloves. I noticed one of my friends had her poncho hood pulled up and secured in place under her helmet so I did the same.

The three things I give the most credit to for keeping me comfortable throughout the miserably wet and cold ride were…

  1. Switching to a long sleeved jersey
  2. Keeping my hands dry with rubber gloves
  3. Keeping my head and neck dry with my poncho hood securely tucked under my helmet

Bill would tell you that his waterproof socks (affiliate link) were what he credits for keeping him the most comfortable. Our teammates later accused him of holding out on them by not telling them in advance that such things exist!


The Ferry Ride

After riding our bikes to the ferry entrance, we were sniffed by security dogs and then ushered into a caged holding area until the ferry got back to port and was ready to be loaded. Dismounted, we pushed our bikes onto the ferry for the ride to Manhattan.

Five Boro Bike Tour


While our Cruiser friend Chuck and I were taking pictures of each other, a nice lady offered to get one of us together.

Five Boro Bike Tour


But First, Breakfast

Once the ferry docked in Lower Manhattan, we hopped on our bikes and rode several miles through a park to grab breakfast. Another benefit of riding with Five Boro Bike Tour veterans was not having to think about where to eat breakfast.

Five Boro Bike Tour


We rode along a few mostly empty streets until we pulled into the Good Stuff Diner on 14st Street. I headed straight to the restroom and as I returned to the table, our waiter was already wrapping up taking our orders. When he asked if I knew what I wanted, I rattled off, “Hot chocolate, pancakes, scrambled eggs, and extra crispy bacon.” I wanted something substantial and was thrilled that I didn’t have to worry about upsetting my digestive system like I do when running.


First Borough:  Manhattan

While we were finishing up our breakfast, the first wave of the Five Boro Bike Tour was being started. It was time for the Trumpet Heads to finish our delicious meal and join in on the fun. Well-fueled, we were ready to take on forty soggy miles through the streets of New York City.

Five Boro Bike Tour

Purchased from Marathon Photo

Our ride down 6th Avenue through Midtown was surreal. With our slower pace we fell behind our wave and found ourselves almost alone until the next wave caught up with us. We were even scolded by a volunteer for lagging behind! To be fair, though, we had good reason to be riding slower than normal. Paul’s (aka Mr. Incredible) speakers add quite a bit of weight to his bike, so much so, that the combined weight of his speakers and bike is around one hundred pounds. It’s a small price for him to pay to entertain us with music for our ride. 😉

Picture riding down 6th Avenue to Frank Sinatra belting out New York, New York and you’ll get a feel of what it was like to be a Trumpet Head riding in the Five Boro Bike Tour. Watch a soggy police officer dance to Gloria Gaynor’s I Will Survive and you’ll understand why Paul keeps going back with his one hundred-pound bike.

Five Boro Bike Tour


From Midtown, we rode through Central Park to the tunes of The Beatles singing Strawberry Fields Forever. Paul puts a lot of thought into the timing of songs playing along specific parts of the course. He chose Strawberry Fields Forever to play during our ride through Central Park because Strawberry Field is a small section of Central Park that pays tribute to John Lennon, the voice behind Strawberry Fields.


Second Borough:  Bronx

For a hot second we rode through the Bronx after crossing the Madison Avenue Bridge and before returning back into Manhattan via the 3rd Avenue Bridge. I remember seeing a sign that read, “Don’t Blink or You’ll Miss the Bronx.” As we rode back into Manhattan, we passed the ten-mile mark.


Back in Manhattan

We rode for a while in Manhattan where it got quite crowded. As we approached the hill heading up the ramp to the Queensboro Bridge, I marveled at how people were able to stay upright on their bikes while riding so slowly. I honestly thought I was going to have to get off and push my bike, not because the hill was difficult, but because almost everyone around us slowed to a near crawl. The combination of some fellow riders not knowing the importance of gearing down and not having the cardiovascular endurance for maintaining speed on the hills, made for major traffic jams at all the climbs.

Five Boro Bike Tour


Third Borough:  Queens

Once we crossed the river we were in Queens where we rode for somewhere between six and ten miles. By this time we had pulled away from the rest of our team and were riding at our own pace.

Five Boro Bike Tour

Purchased from Marathon Photo

We pulled into the Cliff Blok Party Aid Station to refuel, use the restrooms, and hopefully, rendezvous with the rest of our team. I quickly learned that when riding in a large event, there’s added baggage to worry about – my bike! At first, Bill and I took turns watching each others bikes.

Five Boro Bike Tour


When someone saw Bill taking a picture for my blog recap of me holding our bikes, he offered to take a picture of us together.

Five Boro Bike Tour


Eventually, we decided to prop our bikes against concrete wheel stops, but Zephyr wouldn’t stand so I laid her on her side.

Five Boro Bike Tour


We checked out the map to see just where we were in our journey. Our Garmins (affiliate link) showed that we’d ridden about fifteen miles, but I needed a visual.

Five Boro Bike Tour


The stop was sponsored by Cliff and in addition to bananas, bagels, fruit, coffee, etc., we had a variety of Cliff products from which to choose. There was also had an abundance of porta potties at the rest stop.

Five Boro Bike Tour

Five Boro Bike Tour

Five Boro Bike Tour


While stopped, the rest of our team caught up and we gladly hammed it up for a group photo.

Five Boro Bike Tour


After we left our rest stop, Bill and I picked up the pace as best we could considering the number of bikers around us. We rode through Astoria and under the Hellgate Bridge where Bill’s dad grew up. In the video at the end of this post, you can see me pointing toward the house Bill visited often as a small child.

After riding out of Astoria, we rode along the East River and stopped around the twenty-mile point for a picture. Bill took pictures of three other riders in exchange for a  photo of the two of us.

Five Boro Bike Tour


Fourth Borough:  Brooklyn

We rode into Brooklyn as the rain continued to come down steadily. We made the mistake of stopping at another rest stop. Unfortunately, we had to dismount and walk our bikes for what seemed like forever, but the chance to refuel and use the restroom was worth it.

It’s also worth noting that by this point, my left hand was becoming quite numb and it was difficult for me to tell if I was braking. Fortunately, it was my front brake rather than my rear. Shaking my arm and hand would help for a little while, but soon after putting my hand back on the handlebar it would go numb again. This has happened before and I’m not sure if it’s due to hand placement or perhaps I’m pinching a nerve that feeds to my hand when I sit in my riding position for a prolonged time.

Five Boro Bike Tour


Fifth Borough:  Staten Island

After crossing the lower tier of the Verrazano Bridge (where we were temporarily protected from the rain), we were back in Staten Island and within five miles of the finish line. We actually were able to maintain somewhere around 15-16 MPH as we rode down the expressway leading toward the finish.

Rather unexpectedly and abruptly, we rounded a turn and saw the finish line in front of us. We rode through the arch and eventually slowed to a stop, dismounted, and rolled our bikes as we continued through the finishers’ chute. We were handed a water bottle, mylar blanket, and a surprise medal before being directed to the right to the Finish Festival.

Five Boro Bike Tour

Five Boro Bike Tour


And of course, what event is complete without a picture for #MedalMonday on Instagram?

Five Boro Bike Tour


At the Finish Festival, Bill held my bike while I went into the merchandise tent and looked for the commemorative women’s jersey. Just as I inquired and the young lady at the cash register told me they were all sold out, a guy came from the back and as he held up the jersey, he told the lady he’d just found a women’s small in the back. I asked if I could try it on, and luckily, it fit perfectly!


Riding on high after completing my first Five Boro Bike Tour, my bubble was burst when we had to walk through mud to get out of the Finish Festival and onto the road to ride back to our car. Poor Zephyr got mud all over her tires, and of course, my bike shoes didn’t fare any better. Luckily, we rode through many deep water puddles which cleaned off our bike tires. We even stopped at one and stomped around to clean off our shoes.

Five Boro Bike Tour


And that bike ride back to our cars after completing our forty-mile Five Boro Bike Tour? It was three miles…


The Pros and Cons of Wearing a Trumpet Adorned Helmet

Wearing a trumpet on my helmet wasn’t so bad. I actually forgot that it was up there until I hit it on the inside of a couple of porta potty doors or got a funny smile from someone whose gaze was just about my head.

While on our ride, we got a variety of comments from our fellow riders. We were asked more than once if we were part of a band – a thought that is absolutely hilarious if you’ve ever heard me sing, hum, or try to whistle. While Bill and I were riding without our teammates, we heard the comment, “I bet you two make beautiful music together.” And after we finished our ride, a lady asked for a picture of the two of us together to share with her sister who’s a music teacher.

Several of our teammates were asked if they knew Miles. I already knew that Miles is a legend in several Virginia, Maryland, and Florida running circles, but didn’t know that he’s also a celebrity at the Five Boro Bike Tour. Bill and I were more than a little bummed that it didn’t work out for Miles to ride with us this year.


Post-ride Celebration

Back at our hotel, we showered and took well-deserved naps before meeting our teammates for dinner. Cheers to the Trumpet Heads!


While sitting around the dinner table basking in our job well done, I took notes as my teammates and I reminisced about the the highs and lows of the day. Those notes were incredibly helpful as I pulled together this recap.

One thing we all remembered were the little kids riding on trailer bikes behind their parents’ bikes and their faces getting constantly sprayed from rain water being slung off their parents’ back wheel. Fortunately for us, we were on the other end of the spraying.


Back home, Bill spent the following week pulling down video from his GoPro (affiliate link) and making this fabulous video. For a real feel of what the Five Boro Bike Tour was like, check it out!


Final Thoughts

Bill and I have already decided that there’s a very good chance we’ll be back with the Trumpet Heads for next year’s Five Boro Bike Tour. Yes, the rain was definitely a deterrent this year, but I’m sure it kept many of the 32,000 riders away and gave us less crowded streets.

Tagging along with veteran riders made the event much easier to navigate. From following suggestions on which hotel to book, to knowing what time we’d need to leave the hotel to get to the Staten Island Ferry, to being told the best place to have our post-race celebratory dinner, we were able to rely on the wisdom of our experienced friends.

Our teammate Jeannine summed it up best as she mulled over the day’s cold and soggy weather, “It wasn’t quite as miserable as I thought it would be.”


  • • Have you ridden in a large group ride?
  • • Would you put a trumpet on your helmet? ~ I was hesitant at first, but decided it would be fun and that I should embrace being part of the team. Plus, it really did make it easier to find each other in the crowd of bikers.
  • • What would you have done – ridden in the rain or bailed?