Ride 8: New York
The Empire State
State: New York (#8)
Area: New York City
Route: a peninsula on the north side of Long Island near Glen Cove and Oyster Bay
Final mileage: 50.82
Date: May 29, 2021 (Memorial Day weekend)
New York: the concrete jungle where dreams are made of—or nearly wiped away in a monsoon. Yes, the Empire State was one of the wettest, most difficult, and most frustrating 50-milers we have done to date. In fact, the uncooperative weather precluded us from adding a second state (Connecticut) to our holiday weekend trip to the northeast. This was probably a good thing, as New York kicked our butts from the Bronx to the Catskills and back.
And yet, despite all this—or maybe because of it—our eighth ride in this series was one of the most rewarding rides we have done so far.
As with many other states, New York has several great trails inside its borders. However, there’s just no place like New York City. Moreover, because we had the long holiday weekend and initially wanted to knock out two states, the city’s proximity to Connecticut made it even more ideal for our New York ride.
While New York City does have some trails of its own, they sadly are not very extensive. Building a 50-mile route there have required riding on its busy streets for long stretches at a time. Thankfully, Strava exists, and Alex found some segments just a little ways outside the city on Long Island that offered a scenic New York experience.
So we drove late on a Friday evening from Baltimore to Jersey City, which is situated just across the Hudson River from downtown Manhattan. As a precursor of what lay ahead, we were chased almost the entire way by this monstrosity:

The forecast for the weekend already looked like it wouldn’t be cooperating with us. By the time we got to our hotel in Jersey City, the rain had picked up significantly. We crossed our fingers and hoped we’d get to do even one ride this weekend.
The next morning, on Saturday (the day we had planned to do the New York ride), the rain had slowed to just a drizzle, and the forecast seemed to indicate that it would be completely done by the afternoon! So we decided to take a stroll around downtown Jersey City while the remaining precipitation blew over.
Around noon, we got in the car and took off for Long Island. Unfortunately, this required venturing through downtown Manhattan, which, despite the rain and the fact that this was a holiday weekend during a pandemic, seemed as busy as any other day. Crossing those long 2 miles from the Hudson River to the East River took an inordinate amount of time, and what should have been just over an hour’s drive ended up taking almost two.
This is the part where we admit that our diet on this trip—at least on this particular day—was probably not what you’d recommend for two people spending a weekend doing strenuous physical activity. But alas, given our time constraints, we pulled into a McDonald’s parking lot, snarfed down some nuggets and fries, and departed for our starting point: a small town called Manorhaven, which is about an hour outside of Manhattan and just beyond the reach of the New York City city limit.
This ride followed an especially circuitous route, taking us through several small towns and neighborhoods along the north side of Long Island, including Roslyn, Oyster Bay, and Glen Cove.
Unfortunately—for us and for you, dear reader—shortly after we started riding, the rain returned in fits and starts and remained with us throughout the entire ride. Not only did this force us to mostly focus on just getting through it (rather than taking pictures along the way to share with you), but it also made the ride far more challenging than anything to date—especially when accompanied with the cold and constant elevation change (shown below).

One of the most difficult stretches came around mile 28. Although it was basically flat and, our pre-ride research on Google Street View informed us, should have offered a stunning view of the water in the Oyster Bay National Wildlife Refuge, the steady rain turned into a frigid, torrential downpour just as we hit it. What’s more, compared to most of the ride when we were under the cover of trees on back roads, we were completely exposed during this segment.
Outside of Pennsylvania, this was probably the closest we have both come to calling it quits in the middle of a ride. This stretch was frankly just miserable, and perhaps the only thing that kept us going was our phenomenally waterproof rain jackets. Though our pants and shoes were soaked, our upper halves remained impressively dry thanks to that outerwear.
After we exited this 2-mile stretch, the previously unforgiving rainfall let up just a little and the bike lanes found their way back to some tree cover. From that point on, we were simply determined to finish the ride with our sanity intact.
Now, having said all this, we want to be clear about something: despite the obstacles and unfriendly weather conditions, this area of New York offered us gorgeous views from start to finish. Being Long Island, there was a McMansion on a large plot of land around just about every turn, as well as quaint small towns and plenty of shoreside riding. Given the timing of this ride in mid-spring, the leaves on the trees were the perfect shade of green. We mentioned several times how nice it would be to come back to this area and actually spend some time touring the towns and enjoying their amenities when we weren’t rain-soaked and exhausted.
We ended this ride with a little daylight left and, full of mixed feelings and wet clothes, made a beeline for our other healthy-eating establishment of the day: IHOP. There really is nothing like pancakes, eggs, hashbrowns, and a warm cup of hot chocolate after a day like that.
Given that the rain looked likely to continue into the next day, we called an audible on the way back to Jersey City—our Connecticut ride would have to wait for another time. (This proved to be a wise decision, as it poured all day Sunday.) Instead, because this was Alex’s first time back in NYC since our high school band performed at Carnegie Hall our junior year, we decided to spend the next day just wandering around Manhattan.
Conveniently, we found out that a friend from Alex’s medical residency program in Baltimore would be in town Sunday to visit his wife, so after traversing SoHo for a while, we met up with them at the delicious dim sum restaurant, Tim Ho Wan. After that, we moved quickly through the downpour toward the East Village, where we found a Japanese tea room to chat and wait out the storm.
Alex’s friends eventually took off, and we spent the remainder of our afternoon driving around Manhattan seeing some of the major sights by car: Times Square, the United Nations, Rockefeller Center, Carnegie Hall (of course), and Central Park.
While driving around, we happened upon a tucked away Indo-Chinese fusion restaurant called Spice Symphony, and eating here may have been one of the best decisions of this trip. Highly recommended if you find yourself in town one day and craving Indian food.
We eventually made our way back to Jersey City for one last night in town, and in the morning, we stopped by a popular bagel shop to bring back treats for our gals.
And that’s how this one ends! It was a cold—at times, maddening—adventure, but the food, sights, and company made it all worth trekking around one of the best cities in the world for ride number 8. Until next time, New York...



















