the Annual Five Boro Bike Tour is Cycling Through New York City On A Beautiful Sunday in Spring
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Imagine cycling through all five boroughs of New York City, from lower Manhattan to Staten Island—completely car-free—on a beautiful Sunday in Spring. The annual 5 Boro Bike Tour is pretty darn cool. Think you have what it takes to bike the 40 miles through the greatest city on earth?
This post is the second installment in our Five Boro Bike Tour Series. Meant as a resource for the 32,000-strong cycling community who return year after year—and for those preparing to ride it for the first time—here I share my personal experience riding in this iconic annual event.
For essential resources and important information about the TD Five Boro Bie Tour, see my post, The Five Boro Bike Tour Is The Best Way to Experience New York City. You’ll find all you need to know about the Tour, as well as some Things You’ll Need (and want) For The Five Boro Bike Tour.
Personal Goals for the Five Boro Bike Tour
The Five Boro Bike Tour is a completely unique and personalized experience. Make your goal for the ride whatever you want it to be. Take it fast or take it slow. Ride it like a pro cyclist testing your limits, ride it in cycling teams, or put on a costume and make it party on wheels with friends. Choice is yours. Have fun.
First time Out: My Personal Ride Approach
My approach to the ride was like a personal time trial to test my conditioning. Since this was my first time doing this ride, I wanted to establish a performance baseline. It took me 2hrs 27min to ride the 37.80 miles to the Finish Festival (where there’s a mandatory dismount. Plus additional 3-4 miles to the Staten Island Ferry not included in the stats.). My average speed was over 15mph.
For the next time I ride the Tour, my goal is to crush my previous time.
Better Late Than Never: I Finally Signed Up for the 5 Boro Bike Tour
I registered late for the Tour—just two weeks before it took place. I’d been wanting to do the ride for years but never really knew when it happened. Plus, I’ve been riding an old bike that’s too small for me, and I rarely ride outdoors anymore. That alone made the idea of riding 40 miles through all five boroughs feel a bit daunting.
Then I discovered Unlimited Biking and realized I could rent a properly fitted bike for the 5 Boro Bike Tour. That made everything click into place, and I decided to go for it and registered.
Once I signed up, I knew I needed to be ready for game day. While I rarely ride outside, I do ride regularly on Peloton and feel pretty well conditioned for long rides. Still, I wanted to make sure I was fully prepared, so I trained on my Peloton.
If your curious to know if training on a Peloton will prepare you for a road ride, see my next post: How I Prepared on Peloton for the 5 Boro Bike Tour.
Set Your Goals Before You Roll: How to Approach the TD Five Boro Bike Tour with Purpose
What’s your goal for the 40 mile Tour? Depending on how much you ride and your fitness level, considering preparing for the ride. Whether it’s your first time or your fifteenth, setting your intention for the Tour in advance can completely transform your experience. Here’s why that matters—and how to make your goal a reality.
Note: a 40 mile ride is manageable without special training. But if you’ve never done the Tour, or cycled this distance in a single session before, consider familiarizing yourself with some train tips.
See here for Things You’ll Need (and want) For The Five Boro Bike Tour
Why Setting a Goal Matters
1. It gives your training a purpose.
When you know why you’re riding—whether it’s to finish strong, enjoy every moment, or hit a personal time milestone—you’re more likely to stick to a consistent training routine. It turns random rides into focused preparation.
2. It shapes your pacing and mindset on ride day.
Without a goal, it’s easy to get swept up in the excitement or bogged down by frustration (yes, the bridges are real, and so are the bottlenecks). A clear intention helps you stay grounded and responsive to the ride’s rhythm.
3. It makes the finish line more satisfying.
There’s nothing quite like the feeling of achieving something you set out to do—especially when you’re coasting toward Staten Island Ferry after conquering 40 miles of urban terrain.
Choosing the Right Goal
The best goal is one that matches your current fitness level and cycling experience, while giving you just enough of a challenge to feel proud of. A few common ones:
- Completion goal: Just make it to the end feeling good (perfect for first-timers).
- Time goal: Aim for a certain pace or finish window (note: this is a ride, not a race, so you’ll need to plan around crowds).
- Enjoyment goal: Take your time, soak in the city views, and stop often.
- Team/charity goal: Ride with a group or in support of a cause.
How to Achieve It
1. Train with intention.
In the 6–8 weeks leading up to the ride, incorporate a mix of short weekday rides (10–15 miles) and one long weekend ride (build up to 30+ miles). Include some hill work—those bridges will test you.
2. Simulate the course.
Try to replicate the stop-start nature of the Tour. Practice riding in groups, navigating crowds, and maintaining energy with frequent slowdowns.
3. Plan your ride-day logistics.
Start time, ferry plan, gear, snacks, hydration—all these details matter. Being organized keeps your mental space clear for the ride itself.
4. Fuel and recover smart.
Don’t try anything new on ride day. Eat a balanced breakfast, stay hydrated, and bring easy-to-digest fuel for the ride. Afterward, take time to stretch and replenish.
5. Stay flexible.
Even with a goal, be ready to adapt. Weather, crowding, or unexpected delays may pop up. Keep your mindset relaxed and focus on enjoying the ride.
Final Thoughts
The TD Five Boro Bike Tour is more than just a ride—it’s a celebration of cycling, community, and the city itself. By setting a goal, you’re not just preparing for a better Tour—you’re creating a more meaningful and memorable experience.
So whether you’re riding for the view, the challenge, or the sheer joy of it, define what success looks like for you. Then get on the saddle and go claim it.
