I biked 40 miles, here’s how you can too

The Five Boro Bike Tour is an annual 40 mile ride through closed city streets across all five boroughs of New York City. The ride is on wide, paved roads with a few long inclines on bridges. As a NYC cyclist, it has been on my bucket list, not for the distance, but for the experience of riding on landmarks like the FDR Drive and the Verrazzano-Narrows Bridge, which are typically car-only roads.

When I told the rest of the NBC Select team about the ride, the response was mostly, “40 miles? That’s so far. I could never do that.”

I’m here to tell you (and my coworkers) that you can, all it takes is a moderate level of fitness, preparation and gear. While I can’t help with the fitness part, I can share the essential gear that made my 40 mile bike ride easier, even with the rain.

SKIP AHEAD Navigation | Helmet | Cycling Shoes | Eyewear | Apparel | Bike bell | Hydration | Storage | What else to consider for long distance cycling

$0.00

Apple

$0.00

Google Play

$0.00

Ride with GPS

$0.00

Apple

$0.00

Google Play

$49.95

Peak Design

$49.95

REI

$279.99

Amazon

$280.00

REI

$279.99

Wahoo Fitness

The Five Boro Bike Tour has a set route but outside of large events like these, you get to create your own route. Your route is the most important part of any ride, in my experience. After all, riding 20 miles through busy city streets is very different from 20 miles of flat paved bike paths.

I tend to plan all my routes in advance. I look at apps like Google Maps and Ride With GPS to find recommended bike routes with little to no car traffic. When it comes time to ride, I use a GPS device, either my phone or my bike computer, which is mounted on the stem or handlebars of my bike.

For short rides in the city, I slot my phone into the Peak Design universal bar mount. This requires a Peak Design phone case or universal adapter. For longer rides outside the city, I upload routes to my bike computer — I use the Wahoo Elemnt Bolt linked above, but have heard good things about Garmin bike GPS as well.

Bike helmets can reduce the risk of head injury by more than 50 percent, according to a report by the National Safety Council, a non-profit safety advocacy group. I’ve worn helmets that cost $30 and helmets that cost $250 — the cheaper ones tend to squeeze spots on my head instead of distributing weight evenly across. An uncomfortable helmet isn’t that big a deal for a quick 15 minute ride, but for a five hour long one, it can give you a literal headache, in my experience.

I’ve worn the Smith Trace helmet for over two years. It’s the most comfortable helmet I own, and feels great on my head even after five plus hours of wear. It is a bit expensive at full price — you can find other options in our guide to the best bike helmets.

$120.00

Adidas

$120.00

REI

$42.00

$140.00

Adidas

$120.00

REI

$160.00

Specialized

$120.00

$170.00

Jenson USA

There’s nothing stopping you from cycling long-distance in regular sneakers, but I think you’ll be a lot more comfortable in dedicated cycling shoes. Cycling shoes have a stiffer sole that better converts your pedaling efforts into energy and better distributes force across the pedal, reducing the chance of hotspots, according to experts.

I, and cycling experts I’ve spoken with, recommend mountain bike cycling shoes for most people — they are much more comfortable to walk in than road biking shoes, and have many of the same benefits. I’ve used the flat-pedal Five Ten and clip-in Specialized shoes linked above to ride on paved, dirt and gravel roads.

If you live in a colder climate, a comfortable pair of merino wool socks can also go a long way in keeping your feet dry, warm and comfortable for your entire ride.

$45.00

Goodr

$45.00

Performance Bicycle

$222.00

Amazon

Good sunglasses means less squinting, and an easier time seeing what’s on the road ahead of you. For cycling in particular, protective eyewear shields your eyes from incoming dust, debris and wind, all of which can make your eyes water and make it harder to see.

While pricey, I find transition sunglasses the most versatile, I can wear them on sunny, cloudy, rainy or snowy days without issue.

$19.53

$25.00

Amazon

$67.50

$90.00

Amazon

$67.50

$90.00

Gorewear

$69.00

Patagonia

$110.00

Rapha

$109.00

REI

$109.00

Dick's Sporting Goods

$109.00

Patagonia

$375.00

Rapha

You don’t need to buy a bunch of skin-tight cycling clothes to go on a long bike ride. I’ve ridden dozens of miles in everything from a t-shirt and shorts to some of the more technical clothes linked above.

I find a few pieces of apparel more valuable than others. Gloves are at the top of my list — riding with freezing hands is miserable, and any pair of gloves goes a long way in preventing that. Second is bike shorts — the built-in padding eases some of the bum soreness I inevitably have after a long ride. Third is a windbreaker or rain-proof outer layer, depending on the weather.

$34.99

$36.99

Amazon

$31.99

Soma Fab Shop

$31.99

Crane Bell

$26.25

Amazon

$21.99

Soma Fab Shop

$21.99

Crane Bell

I am a huge fan of bike bells, despite the fact that I rarely see them on other cyclist’s bikes. They are one of the easiest ways to communicate to pedestrians and other cyclists while riding.

I’ve used Crane Bells for years — they strike a great balance between durability, loudness and price. The Crane E-Ne model fits drop-bar bikes well, while the Crane Suzu is a better fit for flat bar bikes. I recommend the brass versions of both — they are louder than the aluminum ones, according to the brand.

$16.00

Amazon

$16.00

Polar Bottle

$6.00

Amazon

$6.00

REI

$6.00

Planet Bike

$15.44

Amazon

$11.00

REI

$10.99

Lezyne

$29.95

REI

I try to take a sip of water for every mile I ride. Most bikes have a place to mount a water bottle on the downtube of the frame — this makes it easy to reach for and grab while riding. The Polar Bottle and Planet Bike cage linked above are what I started cycling with, and work flawlessly after years of use.

If you are mountain biking, consider a stronger and more durable bottle cage like the Lezyne Power Bottle Cage. Better yet, attach a stem bag to your bike for easy access to your bottle and more room for a large frame bag.

$26.25

$35.00

Green Guru Gear

$26.25

$35.00

Alchemy Goods

$33.03

$40.00

Amazon

$30.00

$40.00

Green Guru Gear

$30.00

$40.00

Alchemy Goods

$19.99

Priority Bicycles

These are the bags I have on my bike, but there are tons of other brands that make highly-rated bike bags for storing your stuff (Ortlieb, Revelate Designs, Oveja Negra and Outer Shell come to mind).

The purpose of bike bags is to be able to carry all of your stuff without having to lug around a heavy backpack, which can strain your back. Some bags, called panniers, attach to a metal cargo rack on the rear of your bike, while others (like the ones above) have velcro straps that fasten to different parts of the bike frame.

On any given ride, I typically have a top tube bag, frame bag and saddle bag attached to my bike. Here’s what I put in each bag:

If you have a working, well-maintained bike that you feel comfortable riding, you should ride it. You don’t need a high-end $3,000 road bike to ride 40 miles — it may make the ride a little faster or a little easier, but not enough to call it a necessity.

I ride a Salsa Journeyer Apex 1, but have done long-distance rides on commuter, folding and ride-share bikes. During the Five Boro Bike tour, I saw every bike imaginable at the start and finish line — you don’t need to ride something that looks fast to go the distance.

The 40 mile Five Boro Bike Tour may seem intimidating to you, and that’s okay. Find or make a route that’s right for you, whether that’s a 3 mile loop around your neighborhood or a couple thousand miles across the USA.

What I find more intimidating than distance is car traffic. I find biking among cars stressful and nerve-racking, the opposite of the peace and quiet I am looking for while riding. That’s why I look for off-road trails when planning a long-distance route. In the eastern US, there are a lot of rail trails — old railroads converted into car-free pathways for pedestrians and cyclists. The Empire State Trail, for example, is a 750 mile, largely car-free trail across the state of New York. You can find car-free trails using resources like Ride With GPS, Trail Link, Bikepacking.com and by connecting with local cycling clubs in your area.

Not only does it mean you’ll have people to talk to, it also means that someone can watch your bike when you inevitably need to go to a rest stop or cafe to use the restroom. Most of my favorite bike rides have been with friends — riding 30 miles through woodsy rail trails or 50+ miles across multiple suburban counties, with plenty of stops for breaks, snacks and pictures.

You can find my video recap of the Five Boro Bike Tour below.

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Harry Rabinowitz is a reporter at NBC Select who covers technology and fitness including guides to fitness trackers, cycling shoes and workout headphones. He has ridden around New York state for years on all kinds of bikes.

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Harry Rabinowitz is a reporter for Select on NBC News.