Ultimate Guide to Biking to all of New York City’s Landmarks

The easiest way to hit all the iconic New York City landmarks is not by taxi, but by bike. We embarked on the ultimate day of biking for the full Big Apple experience with the Hudson River Greenway being the highlight of the day. Read further to ride from Coney Island, over the Manhattan Bridge to the Statue of Liberty and everything in between.

Our adventure started near Times Square with our first destination being Coney Island about 16 miles away. We headed out early because this first half of the ride was mainly street biking and we wanted to beat some of the traffic. First we followed 9th Ave through Chelsea and then crossed over to Bleecker St. We then snaked our way a few blocks down to cross the Manhattan Bridge. 

The Manhattan Bridge is at the 5 mile mark and the bridge itself is 1.3 miles long. There is a separate bike pathway across the bridge that is lower than the roadway, but even with the subway tracks. Unfortunately this blocks most of the view and is very loud when a train passes by. The path itself is fairly skinny, so beware of passing cyclists.

After leaving the bridge, we went from Jay St. to Dean St. to Berkeley Place to finally reach Prospect Park after 3 miles of street biking. Follow West Dr nearly 2 miles through Prospect Park to Ocean Parkway at the South end of the park. The wide bike path through the park is split between bikes and pedestrians and runs in a one-way, counter-clockwise direction. It feels like a mini Central Park and was a nice relaxing break from the prior street biking and navigation.

Ocean Parkway was the country’s first bike path, completed in 1894. So of course we had to make sure to ride it and thank the trail for being the first bike trial of many! Annoyingly, the bike path is more like a sidewalk these days. At every cross street we had to stop and wait for the traffic light to change. This made for a very slow 5.5-mile ride. The path itself is pretty bumpy as well so be prepared for a more leisurely pace during this stretch. 

We stayed on Ocean Parkway until it ended at Hennessey Triangle where the road turns into Surf Ave. Here we hopped on the Coney Island Boardwalk, also known as the Riegelmann Boardwalk. Don’t forget to take a picture with the Coney Island Beach sign before heading up to the boardwalk. The boardwalk is only open to bikes between 5am-10am so plan accordingly. None of the attractions were open yet, but it was fun to take in the sights, and of course the famous Nathan’s Hot Dog stand before the crowds arrived. 

The boardwalk is about 2 miles long and ends at W 37th St. Then it’s back to some more street biking along W 37th St. to Neptune Ave to Cropsey Ave until you meet up with Shore Parkway. This isn’t the nicest area of Brooklyn, but there is a dedicated bike lane for the majority of the way. Shore Parkway is a one way road with a protected bike lane for the first mile and then turns into an actual multi-use path along the water. 

Ride the path, which follows Belt Parkway, for about 4.5 miles while enjoying views of the water and passing under the Verrazzano-Narrows Bridge. After reaching Owl’s Head Park, you’ll be back to street biking largely on 4th Ave. Our destination was now Brooklyn Bridge Park 6.5 miles away. Stay on the bike lane of 4th ave until you reach 9th street. Then to Clinton, Kane and Columbia Streets which all have bike lanes. These three streets are also all one-ways which decreases the traffic and makes for an easier ride. 

Once you reach Brooklyn Bridge Park-Pier 6, you’ll be able to hop on the Greenway Path. Snake your way along or around the multiple park until you reach Brooklyn Bridge Park-Pier 1. This Pier especially has fantastic views of the NYC skyline and both the Manhattan and Brooklyn Bridges. These piers are pretty busy so watch out for pedestrians. They also have some of the most scenic soccer fields and basketball courts I’ve ever seen.

At this point in the ride we were just under 34 miles in and in desperate need of a pizza break. We stopped for a lunch break and explored the DUMBO area (Down Under the Manhattan Bridge Overpass). We tried a slice at Grimaldi’s Pizzaria, but the highlight for my husband was trying an authentic egg cream. This drink is made from whole milk, soda water and Fox’s U-Bet chocolate syrup. As an avid chocolate milk lover, this is what he was most excited for and was not disappointed. The egg cream was invented in Brooklyn so we couldn’t miss out. 

After resting our legs and fueling up, we were ready for part 2 of the journey. Our end destination now was back to our hotel near Times Square, but we had quite a few stops along the way planned. First, we headed over the Brooklyn Bridge back into Manhattan. This bridge is 1.1 miles long and similar to the Manhattan Bridge, has a separate bike lane. Although the view isn’t as unobstructed as the pedestrian pomade on top of the bridge, the view is still pretty spectacular. 

The Brooklyn Bridge was built in 1883 and was the longest suspension bridge in the world. Of the two bridges, this one was my favorite and I highly recommend riding or walking across it even if you don’t do the rest of the ride. We did a quick pit stop to the New York City Hall so I could pick up a bike-themed magnet. Then we snaked our way South through some very skinny one-way streets to meet up with the East River Greenway.

It’s a short 0.7 mile ride to reach The Battery. Be prepared for some serious crowds around this park as it’s home to the Statue of Liberty viewpoint and cruise tours. In fact, we had to walk our bikes through this area due to the amount of people. I wasn’t overly impressed by the Statue of Liberty from this vantage point. Lady Liberty is so far away it’s difficult to see. We did not take a tour either, instead opting for a generic sightseeing cruise that just got close to the statue, but did not stop at Ellis Island.

We then headed up a block to Bowling Green Park which is New York City’s oldest public park built in 1733. Just above the park where Broadway splits into a triangle is the charging bull sculpture. This bronze sculpture is the symbol of the stock market and is supposed to mean good financial luck. While we were in the Financial District we biked by the NY Stock Exchange and then down Wall St. 

A couple blocks over from the Stock Exchange off Greenwich Street is the 9/11 memorial pools and museum. This was a must see for us. Unfortunately the museum was closed when we were there, but just seeing the memorial pools was so powerful and emotional. You also get a great view of the new Freedom Tower and the World Trade Center. Look for the biking animals sculpture right next to the trade center. 

There is an observatory at the top of the Freedom Tower, which is the tallest tower in the US. We instead opted for the Empire State Building and the Top of the Rock observatories because we wanted a view of Central Park. 

Just across West St lies the Empire State Trail. This bike trail is 750 miles total and is the longest multi-use pathway in the country.  It runs from Buffalo to Albany, Albany to the Canadian border and New York City to Albany. It was just about 4 miles along the trail until we hopped off near the Intrepid Museum and headed back to our hotel. 

The Empire State Trail is also known as the Hudson River Greenway in this section of NYC. It was beautifully paved and had great views of the water, skyscrapers and especially the Freedom Tower. It was definitely the highlight of the ride. The trail continues for miles North of where we ended our ride. Cycling more miles on this greenway is on the agenda for our return trip to New York whenever that might be. 

We arrived at our hotel exhausted from the nearly 7-hour, 45-mile round trip. However, it was everything we dreamed biking in New York would be like. Biking to all the sights was so much more satisfying than taking a bus tour. Biking is also so commonplace around the city that even the on street biking was not intimidating. 

For families or the less experienced biker, I would stick to the Hudson River Greenway, to the Battery and over the Brooklyn Bridge. This is about a 16 mile out and back ride from Times Square with very minimal street biking and still allows you to bike to some iconic New York City landmarks. 

Obviously you can’t visit New York without sampling a thin crust slice of pizza! New York is known for their crispy, but flexible crust and to eat it properly you have to fold it in half. Joe’s Pizza is the most popular place in Times Square, but it had a huge line every time we were near. We opted for 2 Bros Pizza instead and it was delicious! Most places you can buy it by the slice and I think we had at least one slice every day. Chicago was our first stop on our East coast biking adventure and I did not enjoy their deep dish pizza. New York is much more my style!