New York City’s relationship with the bicycle has been a 150-year rollercoaster – from Victorian-era “wheelmen” wobbling on penny-farthings to modern commuters gliding through protected bike lanes. Every turn in this saga has been marked by excitement, backlash, activism, and policy change. Let’s take a ride through the key eras and milestones in NYC cycling history, and see how a once-novel contraption became an integral part of the city’s transportation fabric.

The Gilded Age Bike Boom – Penny-Farthings and New Freedom

In the late 1800s, a strange new machine began appearing on New York’s streets: the high-wheeled penny-farthing bicycle, with one gigantic front wheel and a tiny rear wheel. These contraptions were all the rage in the 1870s and 1880s, but falls from a penny-farthing could be literally bone-breaking. By the 1890s, however, the safer “safety bicycle” took over, making cycling accessible to a broader public.

NYC’s first bike boom was both a practical trend and a powerful symbol of freedom. Cycling clubs sprang up, races drew crowds, and weekending “wheelmen” (and “wheelwomen”) toured the parks. Madison Square Garden, originally designed for cycling races, hosted six-day endurance events at the height of the craze.

Cyclists quickly fought for their rights. The Parks Department initially banned bikes in Central and Prospect Park, bowing to complaints that they endangered pedestrians. But riders pushed back, and by 1883, the ban was overturned. In 1894, Brooklyn opened the Coney Island Cycle Path, one of the first dedicated bike paths in America.

For a brief moment, it seemed the bicycle might reshape urban transportation before the automobile even arrived. In fact, Police Commissioner Theodore Roosevelt created NYC’s first bike-mounted police patrol in the 1890s.

Early 20th Century: Pedaling Through Progress and Hard Times

As the 1900s dawned, bicycles remained popular, but with growing automobile use, cycling shifted toward recreation rather than daily commuting. During the New Deal era of the 1930s, public parks and parkways integrated bike lanes and greenways as part of infrastructure projects.

However, urban planner Robert Moses—who shaped much of modern NYC—dismissed bicycles as serious transportation, famously declaring in 1938 that “bicycles have no place on public highways.” As post-WWII America embraced car culture, NYC’s streets became increasingly hostile to cyclists.

Yet, bicycles persisted. By the 1960s, bike clubs, Sunday riders, and kids on Schwinns kept cycling alive in the margins. New York's first commuter cyclists found themselves navigating traffic on streets designed almost entirely for cars.

Messengers and Mayhem: The 1980s Bike Courier Boom

Fast forward to the 1970s and 1980s, and the stage was set for a bicycle comeback in NYC, thanks to the bike messenger boom. Couriers weaving through gridlocked Midtown traffic became an essential part of the city’s economy, proving that bikes were still one of the fastest ways to get around Manhattan.

However, their high-speed riding style sparked controversy. By 1987, Mayor Ed Koch attempted to ban bicycles from Midtown during business hours, largely targeting bike messengers. The backlash was immediate—cyclists took to the streets in mass protest, leading to one of the most significant bike uprisings in NYC history. The ban was ultimately overturned, but the clash underscored an ongoing fight for bike access in the city.

Taking Back the Streets: Critical Mass & Bike Lane Battles

By the 1990s, NYC’s cycling culture had split between advocacy groups pushing for safer bike infrastructure and renegade activists participating in Critical Mass rides. Critical Mass, a leaderless group ride, flooded the streets on the last Friday of every month, demonstrating that bikes were traffic, not an obstruction to it.

City officials, however, weren’t fans. In 2004, during the Republican National Convention, NYPD launched a brutal crackdown on Critical Mass riders, arresting over 250 cyclists in one night. The battle over street space was heating up.

Meanwhile, a quieter revolution was happening: New York began installing bike lanes—and this time, they weren’t getting ripped out like in previous decades.

The 21st Century: NYC’s Bike Infrastructure Revolution

Starting in the late 2000s, the administration of Mayor Michael Bloomberg and Transportation Commissioner Janette Sadik-Khan ushered in a bike lane boom. NYC added protected bike lanes, redesigned intersections, and made cycling safer than ever before.

By 2013, NYC had built over 400 miles of bike lanes and cycling had tripled from a decade prior. In 2017, Central Park and Prospect Park finally went car-free, marking a major victory for bike advocates.

Citi Bike: The Game Changer

Launched in 2013, Citi Bike transformed cycling in NYC. Initially met with skepticism, the program quickly became a massive success. By 2019, Citi Bike logged over 90,000 daily rides, and expansion plans aimed to reach 40,000 bikes across the five boroughs.

Today, Citi Bike has 1,900 stations and 33,000 bikes, making it one of the largest bike-share programs in the world. The blue bikes are everywhere—ridden by tourists, commuters, and delivery workers alike.

The Future of Cycling in NYC

Cycling is bigger than ever in NYC, with over 600,000 daily bike trips. Yet, challenges remain: bike lane enforcement, e-bike integration, and traffic safety are ongoing battles. With congestion pricing set to begin in Manhattan and more greenway projects in development, the next chapter of NYC cycling is just beginning.

From penny-farthings to police crackdowns, from Critical Mass to Citi Bike, NYC’s cycling history has been a fight for space, safety, and recognition. But one thing is clear: bikes are here to stay, and their best days in the Big Apple are still ahead. 🚲

Want to Ride Through Cycling History?

Join Secret City Bike Tours for an immersive, guided bike ride through NYC’s most iconic cycling routes. Book your ride today!