TD Five Boro Bike Tour – Bike New York 2025: Tips, Highlights & Team Traditions
There’s no better way to experience New York City than on two wheels—and the Five Boro Bike Tour proves it every year as our crew plans for this annual ride. This past weekend, our group of six set out to conquer the 40+ mile ride through all five boroughs: Manhattan, the Bronx, Queens, Brooklyn, and Staten Island. With streets cleared from any type of traffic, as well as nothing but cyclists around us, the city felt electric from start to finish.
This marked our fourth year riding together as a crew, and at this point, it’s more than just an event—it’s a tradition. Every year, we train a little, talk a lot of smack, and take on the city like it’s our own personal course. It’s become a spring ritual that keeps us connected, moving, and motivated. Even while as said our goodbyes and farewells — we always say “Until next year!”
We kept a solid pace and finished in just about three hours (some of us finished a little less). Around the halfway point in Queens, we took a break at a rest stop where volunteers handed out snacks, water, and much-needed encouragement. The energy was high and the support stations were well-run—just what we needed to recharge and refuel for the next 20ish miles.
The toughest part of the ride came at the very end: the Verrazzano-Narrows Bridge. It’s a long, steady climb that tests your legs after so many miles. Even before the bridge, the Brooklyn Express-way (BQE) highway serves an incredible challenge as it’s also a climb that creeps up on you. As I creeped up the inclines, the reward was unbeatable—coasting down the final stretch into the Finish Festival with music, cheering crowds, and fellow riders all around gathering with their medals. That downhill moment felt like flying, and it made every mile worth it in the end.
10 Tips for Crushing the Five Boro Bike Tour
Whether you’re a first-timer or coming back for more, a little prep can go a long way. Here are 10 tips based on our experience to help make your ride smooth, safe, and unforgettable with your crew:
1. Bring a Lightweight Rain Jacket
Weather in NYC can change on a dime. Even if the forecast looks clear, a sudden drizzle can hit mid-ride—so pack a compact, waterproof layer that fits in your bike bag or fanny pack. Staying dry makes a huge difference in comfort and performance.
2. Hydrate Consistently from Start to Finish
Bring your own water bottle and refill it at hydration stations throughout the route. Dehydration can sneak up on long rides, especially in warmer boroughs like Queens and Brooklyn. Take small sips regularly—even if you don’t feel thirsty yet.
3. Wear a Helmet — It’s Required and Smart
The tour has a strict helmet policy, and safety should always come first. Choose a helmet that fits snugly and offers solid ventilation. If you haven’t replaced yours in a few years, this is a great excuse to upgrade to one with newer safety tech like MIPS.
4. Use Padded Cycling Gloves
Over 40 miles means constant grip on your handlebars—padded gloves help reduce fatigue and absorb road vibration. They’ll also keep your hands warm in early morning temps and prevent blisters or hot spots as the ride goes on.
5. Leave the Backpack at Home
Backpacks aren’t allowed on the ride, and for good reason—they can throw off your balance and strain your shoulders. A fanny pack or small under-seat bike bag is the way to go for carrying essentials like snacks, sunscreen, ID, and your phone.
6. Get a Pre-Ride Bike Tune-Up
A quick tune-up can prevent major headaches mid-ride. Check tire pressure, brakes, and gears at your local bike shop the week before. The smoother your ride, the more energy you’ll save for those final bridges.
7. Arrive Early to Your Start Wave
Getting to the start line early gives you time to stretch, find your crew, and soak in the energy of the day. Each wave is timed, so make sure you know yours and aim to arrive 30–45 minutes ahead for a smooth rollout.
8. Dress in Layers That Breathe
Morning temperatures can be chilly, but once you get moving, your body heats up fast. Wear moisture-wicking base layers and add a zip-up or arm warmers that are easy to remove on the go. Avoid cotton—it’ll trap sweat and slow you down.
9. Double-Check Your Start Info the Night Before
Each rider gets assigned a start wave and location—don’t assume it’s the same as last year. Confirm your wave time and access point the night before, and plan your route to the start accordingly to avoid confusion or delays.
10. Enjoy the Ride and Soak It All In
This isn’t a race—it’s a rolling tour through NYC’s most iconic streets and bridges. Take in the skyline views, ride alongside strangers who feel like teammates, and stop for a selfie or two. The ride is about the journey as much as the finish.
Final Thoughts: Tradition, Teamwork & Post-Ride Pints
What makes this tour so special isn’t just the ride—it’s the tradition we’ve built around it. This being our fourth year, it’s become an annual reset, a reminder that friendships and shared goals are worth carving time out for.
And of course, we wrapped it up the only way we know how—celebrating with pitchers at Randolph Beer in DUMBO, recounting the climbs, the close calls, and the unbeatable vibes of another FiveBoro in the books.
If you’re thinking about signing up next year—do it. You’ll see the city like never before, meet incredible people, and maybe even start a tradition of your own.
