Forty miles. Five boroughs. Zero cars.
That’s the pitch. It sounds simple, maybe even a bit relaxing, until you’re standing at the starting line in Lower Manhattan at 7:30 AM on a damp Sunday in May. The air smells like chain grease and expensive espresso. You are surrounded by 32,000 people. Some are wearing full aerodynamic spandex like they’re chasing a yellow jersey, while others are riding rusted beach cruisers in tutus. It’s chaos, but it’s organized chaos.
The TD Five Boro Bike Tour is weird. It’s the largest charitable cycling event in the United States, run by Bike New York. It’s also one of the only times you can legally ride a bicycle across the Verrazzano-Narrows Bridge without getting arrested or blown into the Atlantic Ocean. Honestly, if you live in NYC or you’re just visiting, this ride is a bucket-list item that manages to be both totally exhilarating and occasionally very annoying.
What the TD Five Boro Bike Tour Actually Feels Like
People think this is a race. It isn't. If you try to treat it like a time trial, you’re going to have a bad time. You’ll spend half the morning yelling "on your left" at a family of four from Ohio who are just trying to look at the Chrysler Building. The reality of the TD Five Boro Bike Tour is that it’s a massive, slow-moving parade on two wheels.
You start in Manhattan. The skyscrapers make the wind swirl in strange ways. You head north through Central Park—which is the easy part—and eventually cross into the Bronx. The energy changes. People are out on their stoops cheering. Then you loop back down the FDR Drive. This is where it gets cool. Usually, the FDR is a parking lot of angry taxi drivers and delivery vans. During the tour, it belongs to you. The silence of 30,000 bikes humming along the pavement is something you don't forget.
But then comes the BQE.
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Let’s be real: riding on the Brooklyn-Queens Expressway sucks. It’s paved with what feels like broken dreams and jagged moon rocks. Your teeth will rattle. You’ll see at least ten people on the side of the road upside down, trying to fix a flat tire. This is the "grind" portion of the day. You’ve done about 25 miles, your legs are starting to feel heavy, and you realize you still have to get to Staten Island.
The Logistics Nobody Tells You About
Registration isn’t cheap. It usually hovers around $130 to $160 depending on how early you jump on it. People grumble about the price every year. "Why should I pay to ride on streets my taxes already fund?" Well, you're paying for the permits, the NYPD rolling closures, the marshals, and the heavy-duty mechanical support. Also, the money goes to Bike New York’s education programs. They teach kids and adults how to ride for free. It’s a good cause, even if your wallet feels a little lighter.
You also need to think about the "waves."
The tour starts in waves based on your projected speed. If you’re a serious cyclist, try to get into Wave 1. If you end up in Wave 4, you’re going to be dodging "Freds" (cycling slang for casuals with no gear) all day. Expect bottlenecks at the water stations. Astoria Park is a popular rest stop, but it can get packed. Pro tip: pack your own PB&J and just keep rolling if you want to finish before the sun goes down.
Crossing the Verrazzano: The Holy Grail
This is why everyone does it. The Verrazzano-Narrows Bridge is the climax. It’s a two-mile span connecting Brooklyn to Staten Island. Under normal circumstances, bikes are strictly banned.
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The climb is no joke. It’s a long, steady incline that seems to go on forever. You’ll see people walking their bikes halfway up. Don't be that person. Just drop into your lowest gear, stare at the tire in front of you, and breathe. When you hit the crest of the bridge, the view is insane. You can see the entire Manhattan skyline to your right and the open ocean to your left. The wind up there is fierce. It’ll push you sideways if you aren’t careful.
The descent? Pure adrenaline. You hit 30 or 40 miles per hour easily. It’s the closest thing to flying you can get in New York City without a plane ticket.
Common Misconceptions and Why They're Wrong
Some people think the TD Five Boro Bike Tour is only for "real" cyclists. That is totally false. I’ve seen people do this on Citi Bikes. (Note: Don't do this on a Citi Bike unless you have thighs of steel; those things weigh 45 pounds and the Verrazzano will break your spirit).
Another myth is that it’s a great way to "see the sights." You’ll see sights, sure, but you’re mostly looking at the back of someone else’s jersey. If you want a scenic tour of NYC landmarks, take a walking tour. The bike tour is about the vibe of the city and the sheer scale of the event. It’s about the guy blasting disco music from a trailer attached to his mountain bike. It’s about the volunteers handing out bananas like they’re gold nuggets.
What to Bring (And What to Leave at Home)
- A spare tube: Seriously. The BQE eats tires for breakfast. Even if you don't know how to change it, carry one. A marshal will eventually help you, but they can't help you if you don't have the parts.
- Layers: May in New York is bipolar. It could be 50 degrees and raining at the start and 80 degrees by the time you reach Staten Island.
- Water: Two bottles. Don't rely solely on the rest stations unless you like waiting in lines.
- No backpacks: The security rules are strict. You can have a small seat bag or a handle-bar bag, but big rucksacks are a no-go. Check the official Bike New York site for the current bag dimensions before you show up.
The Staten Island Finish Line
Once you get off the bridge, you’re in Staten Island. The ride technically ends at the Finish Festival. There’s food, there’s music, and there’s a lot of tired people sitting on the grass.
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The real challenge? Getting home.
The Staten Island Ferry is the main way back to Manhattan. Imagine 32,000 bikes trying to fit on a boat. It’s a mess. The line can take two hours. Some people choose to ride back across the Goethals Bridge into New Jersey or find a ride in Staten Island, but most just suck it up and wait for the ferry. It’s actually a nice cool-down. You sit on the deck, look at the Statue of Liberty, and realize you just biked through every single borough in one of the most hectic cities on earth.
Real Advice for First-Timers
If you’re thinking about signing up for the next TD Five Boro Bike Tour, here is the truth. Your butt will hurt. You will get frustrated by the crowds. You might even get a little rained on. But when you’re flying down the FDR with no cars in sight, you’ll understand why people do this year after year. It transforms the city into a playground.
Next Steps for Your Ride:
- Check the Date: Registration usually opens in January for the May ride. It sells out fast, often within weeks.
- Tune Your Bike: Take your bike to a local shop in April. Don't wait until the week of the tour—every shop in the five boroughs will be backed up for three weeks.
- Train for Distance, Not Speed: You don't need to be fast, but you do need to be comfortable in the saddle for 4-5 hours. Go on a few 20-mile rides in April to get your "saddle sores" out of the way.
- Plan Your Exit: Decide beforehand if you’re taking the ferry or having someone pick you up in Staten Island. Having a plan prevents a post-ride meltdown.
- Join a Club: If you're nervous about riding in a crowd, join one of the free Bike New York training rides. They’ll teach you how to signal and ride predictably, which makes the whole day safer for everyone.