When you were out and about this Sunday, did you notice thousands of bicyclists riding through the city? I was home sleeping in and after a busy Saturday, but apparently it was the annual Five Boro Bike Tour.

The first spring I lived in NYC, my dad did the Five Boro ride. It was far from a perfect experience for him (I think even the organization admitted that it was not a great year, with problems including the simple but critical one of too many riders) but he enjoyed it enough to suggest we ride it together the following spring.

The Five Boro ride is a forty-mile bicycle tour through NYC. It’s like the marathon, only it’s not a race, and instead of starting in Staten Island, it ends there. The ride begins early on a Sunday morning in May near Battery Park, and goes through (surprise, surprise) all five boroughs.
I agreed to do the ride with my dad the following spring—but first, I needed a bike. 
So not long after my dad rode the Five Boro ride, I bought (with a little help from him) a Downtube folding bike at a local bike shop. It’s light turquoise, and it only weighs about twenty-four pounds—perfect for carrying up the stairs to my old (and new) third floor walk up. I’ve seen too many bikes without wheels, seats, chains, to want to leave my bike outside long term.
I took short rides that summer and fall, the longest being about eight miles. The next spring I got a few longish rides in before it was time for the ride with my dad. The most impressive was a ride from Brooklyn to Astoria to see a friend. I’d ridden to Williamsburg with friends before, but beyond that I had to follow my written directions (I don’t have a smart phone). It was uphill, and something was weird with my gears (I got it fixed before the Boro ride), but I made it there…and took the subway home. Hey, it was late!
I woke up early on the morning of the Boro ride. My parents had stayed in a hotel near the starting point, but I wanted to sleep in my bed.  I rode my bike to a subway line that’d get me to the Battery area quickly and met my parents at the hotel. After a quick, light breakfast my dad and I rode to the starting point. My mom went off to explore the city on her own.
The beginning of the ride was stop and start—it’s too crowded to be anything else—but once we got better spaced out, cruising up 6thAvenue was incredible—all bikes, no cars. If you want a similar experience check out Summer Streets, three weekends each summer when a route from the Brooklyn Bridge up to Central Park is closed to cars and open to cyclists, roller bladers, and pedestrians.
Around midtown I spotted a friend who lived in the area, waiting to cross the street, and I waved and said hello as I whizzed by. In a crowd of cyclists, even with some stops to allow cars to cross 6thAve, I felt fast. The ride passes through Central Park, and while some of the hills there are tough to get up, going down is pure joy—well, pure joy spiced with the danger of going just a little too fast.
The ride lets out at the upper west corner of the park, and after a stop and go ride north it heads east. There was a bathroom stop along that route, where my dad and I called my mom to check in.
There were groups of riders who had come up with themes to make it easy for them to spot each other in a crowd. Some had simple t-shirts, others had flowers attached to their helmets, and it was around that rest stop that we spotted our favorites: Muppet heads. Nothing like a disembodied Miss Piggy head on your helmet to make it easy for your friends to find you.
The ride dips into the Bronx, but only briefly, something like turning a corner, going over a bridge and finding yourself back in Manhattan again just like that, ready to ride south on the FDR. The FDR. Can I stress here how awesome it is to ride downhill on a highway? Remember this for later when I talk about riding the BQE. The FDR was somewhat shady and occasionally passed through tunnels (or it did at least once—my memories are a little fuzzy on these details). But the ride on the FDR is marred only by what waited at the end of our time on it: the Queensboro Bridge.
This was the first major bridge of the ride, and it was steep. If you were having trouble you were supposed to get over to the side and walk up. Great in theory, but in reality the faster riders kept pulling to the side, to pass us slowpokes, and so I rode all the way to the top and gratefully coasted down.
The queens portion of the tour wasn’t as pretty as the ride through Manhattan and the park, but there was a lovely rest stop in Astoria Park, with pretzels and fruit, and then the trek to Brooklyn—which exactly reversed what I’d ridden on my own earlier that spring. It was a lot easier this time, since not only had I gotten my gears fixed, I was now riding downhill.
It was when Dad and I reached Brooklyn Bridge Park, another rest stop, that we had to make a decision. There were still thirteen miles ahead of us. We were hot, and tired, and Mom would’ve liked some extra time with me.
But my completist nature—the part of me that usually reads all of a series and makes my stories overladen with more details than hearers (or readers) need to know—decided we should push on to Staten Island.
So we did.

Remember the FDR? What a lovely ride. The BQE was nothing like that. Except for the very beginning of it, little of the BQE portion was in the shade, and much of it was uphill. And of course, we’d already ridden twenty-seven miles.

This might also be a good moment to mention that I’d forgotten to put on sunscreen on this lovely, sunny May day.

The BQE was torture. We stopped often to rest, and I remember walking my bike up a small hill.

And at the end of it was the Verrazano Bridge.

Neither the Verrazano nor the Queensboro usually allows cyclists, so like riding the FDR and BQE, this was a special experience, and the view of the water was spectacular.

But the Verrazano is a tallbridge, with a deceptive incline. I poured the last of my energy into the climb, then coasted down the bridge and part of the way to the end of the ride.

There was a party—music, food, the works—at the end, but Dad and I headed straight for the long line for the ferry. I stood, half asleep on my feet, leaning on my bike, until it was our turn to board the ferry. I sat down on boards and promptly fell asleep.
It’s been a couple years since I did the Five Boro ride, and I haven’t done that much biking since— and certainly nothing that epic. I am a casual cyclist. I have friends who ride their bikes everywhere, and my dad sometimes bikes to work during mild winter weather. If I could do that I wouldn’t need my expensive gym membership.
But riding those forty miles was exhilarating, and thinking about it makes me want to get back on my bike. And it’s spring! Maybe if I ride a bunch this summer and fall, I can even do the Five Boro Ride again next spring.
Has anyone else done a long bike ride? Any favorite biking destinations or routes in New York?