Recently I've gotten into trying to ride up steep hills. I'll spend a week in NYC starting the 19th. Where should I ride?

In Manhattan the steepest hills would be found in Washington Heights. Or better yet ride across the GWB to NJ and Rockland. Here's a list of grades from the NYC.
https://nycc.org/rides/regional-hill-grades
A lot depends on where you're staying and how far you want to ride

The west side greenway - pretty much flat, EXCEPT, one ridiculous climb from the river up to the level of the GW bridge. That should sort you out.

in NYC, ride for distance and for the experience... hills? "fergittabutit!" For kicks, we Jersey riders invite our NYC rider friends out to do hills, then we practice our CPR skills.

Ride Central Park loops (go early), ride the West Side Greenway pretty much full length of Manhattan.

Take the subway to the Bronx and head into Westchester. Plenty of hills there.

I grew up in NYC, was born & spent some time in central NC and went to college near CLE (Oberlin) thus though I rode a lot not much hill climbing was involved. Then I spent a summer in Berkeley, CA and applied for a job at Orinda Spoke and Pedal on the other side of the Berkeley Hill. The owner asked me to come in for an interview.Stupidly I decided to follow the most direct route, which over a mountain of course means the steepest. I almost died on the way up and got there super late. Got the job, by the end of the summer I was quite the hill climber.

Alpine hill in NJ is a long uninterrupted hill that a lot of riders use. The Bronx has some, upper Manhattan has some. All said though there isn't all that much. The longest hill that I've done in the NYC area is up Bear Mountain on Perkins. That is 1500' and about a 5% steady grade. Compared to the west though it is just a bump in the road. I used it to train for a climb up Mt Haleakala in Maui, but it wasn't enough. Makawao is at 1500', and that is just the beginning of a very long climb.

The steepest (and highest) hills in NYC proper are on Staten Island, which happens to have some pretty decent riding in general. Starting and ending with a ferry ride is a bonus.

Otherwise the closest decent climbs are in Northern NJ starting 10-20 miles NW of the GW bridge. Westchester is also hilly, but decent climbs are all North of White Plains, with higher hills about 40 miles from NYC.

One bonus if you want to ride in Westchester is that you can get a bike pass for Metro North trains, which allow you to bring the bike on board any non rush hour train. So you can leave Grand Central Station and be in North White Plains, which most locals consider the gateway to decent riding here. For bnicer riding you might start farther north ie. Katonah or Goldens Bridge. One nice way to ride in Westchester is to head north form a start in the middle of the county, then loop west and take the train home form somewhere on the Hudson.

Lastly there's excellent steep hill climbing in Connecticutt, just North of Westchester County airport. Or you can ride the rails all the way to Poughkeepsie and explore either the Catskills, or the Central Valley.

Yes, a Bear Mountain ride ride offers about as much climbing as you'll get riding in and around NYC, and is a classic century, starting and ending at the GW bridge, going up one side, crossing the Hudson and back on the other. If a century is beyond your range on a hot summer day, you can take the train to Peeksville, ride to the Bear Mtn Bridge, and go back on the west side of the river.

There's also a pocket of hilly quite roads north of Croton reservoir, between Yorktown and the Hudson. This is especially great riding if you don't bring a map and get lost on these twisty roads.

The worst hill that I know in the four significant boroughs of New York City is short but still terrible. It's Miller Avenue going north from Jamaica Avenue. This is located just a little east of Broadway Junction.

There is a bike lane on southbound Miller. But they don't even bother to put one on the northbound side, evidently on the assumption that no one is going to take it. About ten years ago I decided to ride up this street. There was a guy sitting on a chair at the top of the hill; he applauded when I got to the top. (This was partly out of admiration, but partly communicating the sentiment "we don't see many fools trying that".)

There are worse hills in Fort Lee, New Jersey. I can think of one spot that is really unrideable, but is worth visiting for the unique experience.

If you go north from the George Washington Bridge on Hudson Terrace and turn left at Myrtle Avenue, you soon get to Lemoine Avenue. Just west of there is a huge drop followed immediately by an equally huge climb; the street is shaped like a U. The crazy thing is that the dip and climb are so extreme that, as you are going down the dip, you can tilt your head upward and what you see is not the sky but the road of the coming climb!

Seeing road instead of sky when you look up is disorienting, bizarre, and nothing short of surreal. Then, as you continue through the low point and up the other side, the road seems to move in front of your eyes, as it shifts from above your head down to where it belongs. It's a trippy feeling that is hard to describe.

The worst long-range hill that I have encountered was when I made the mistake of taking Eagle Rock Avenue west from West Orange, NJ to Morris County. I stupidly failed to consult a topographic map, not being in the habit of doing that.

This hill is so extreme that there are signs warning truckers of shifting loads. This is one to avoid; it made the 55-mile ride out to East Hanover more difficult that my rides to Philadelphia which were more than twice that length.

Thanks guys! Any specific hills or routes you recommend?

I'll be staying in Hell's Kitchen. Probably can't go on very long rides most days cuz my sister is flying in from Chicago and will give me a hard time if I spend the whole day riding. But she goes back 2 days before me and will spend a day or two with old friends.

If staying in Hells Kitchen then you might just want to go up the greenway and ride over the GWB and ride up what is known as river road (listed as Henry Hudson Drive on the maps). About 8 miles of mostly flat to the GWB, followed by 8 miles of rolling hills ending with about a 3/4 mile 400 foot climb up the Alpine Approach Rd. You could then return to the GWB via 9W (feels like downhill most of the way) or go back on River Road and do the same hills in reverse. You'd total around 34 to 36 miles

Since you're visiting the city and have limited time, maybe you should try to see the city instead of chasing suburban hills, (though the Alpine ride described before is OK and won't take up too much time.

Possibly the toughest hill in Manhattan, and maybe the whole city excluding Staten Island is Fort George Hill, in Washington heights.

It can be part of a nice ride around Manhattan. Head up Riverside Drive. At 165th Street you'll need to get on the bike path, and continue up to ****man Street, which will take you to the foot of Ft. George Hill. Between 165 and ****man, you might climb up to see the Cloisters. You'll need a lock if planning to go inside, but the grounds are nice to explore.

Once you climb Ft. George Hill, follow the road south and go to Highbridge, which was one of the original aquaducts serving Manhattan and has recently been restored as a bike/pedestrian only bridge to the Bronx. It's worth it just for the view. Then you can head down the hill and pick up the East side bike path to complete your circle of Manhattan. Coming back north don't go straight to the Hudson River, but instead stay more central, so you can explore the various neighborhoods of lower Manhattan, making sure to sample the great food.

Also keep in mind that NYC's bridges are among the highest hills in the city, so be sure to Ride across at least one. Probably the Brooklyn Bridge is the best choice of the East River Bridges. You might use it and the Manhattan Bridge to build a short Brooklyn side loop into you Mahnattan tour.

The fact is that there's plenty of good cycling in NYC. Not the kind of open road scenic riding we look for in the country, but the city is chock full of worthwhile destinations, all accessible by bike. I don't think it's possible to come close to exhausting the option in a week.

That's interesting. How exactly do you get to the greenway at 165th and Riverside?

You know, that's a good question. I grew up in the Bronx, and rode ****man street to what is now the greenway to Riverside Drive countless times, and yet, I can't remember exactly I connected the dots. I do know that coming home, I used to cheat and stay on Riverside Drive until it fed me onto the Northbound parkway, which is very wide in that stretch, and sprint down to the ****man Street exit. This, BTW, is the only way you can get to Ft. Tryon Park and the cloisters from that side. (check the map).

There's been lots of construction since I was there last many years back. I believe that there are now two legal or official options.

1- stay on Riverside Drive until just before it passes under the bridge, and there's a pedestrian cut across the parkway on your left.

2- use 158th Street, which connects to the Greenway, with a bit of a detour. Or pick up the Greenway farther south. (I didn't do that because back then the Greenway was a poorly maintained sidewalk, so getting off it at the first opportunity made more sense)

OTOH - though I can't tell you exactly, I believe you can continue on Riverside a short distance, then work your way to the left at the lights at the bottom of the hill, which is how I used to do it. (it might require a mad dash across the Parkway, but I remember having to do that).

Of course, you can climb 165th street and use city streets to get to Broadway and down to ****man, or enter Ft Tryon Park at the top of the hill, then come back out to Broadway, or go down the hill for the mad dash to the ****man exit off the Parkway.

BTW- I'm sure someone else who's ridden there lately will give you more detailed instructions. For me, it's a matter of habit and something I do but can't explain how.

I grew up in the city, spent several years of my adult life there and have visited repeatedly since moving to Brazil. My focus will be on seeing friends and family and taking care of some matters that need to be dealt with. But I should have time to ride especially when my sister is otherwise engaged. Plus I'll get to see places I've never gone before or haven't been in years or even decades.

You don't have to explain yourself. There are plenty of options here, both within the city and in the surrounding burbs. It's mostly a question of time, weather, and ambition.

Part of the problem is that most of the nicer riding is at some distance from the city, so unless you're considering rides of 75+ miles, a decent portion will be in the close in burbs, which I consider dead air riding, for a bit of nicer riding at the far end of the loop. If you are willing to do a longer ride, look at a map and consider a ride out to Greenwood Lake. Probably the 1st and last 15 miles from the GW will be suburban street riding, but it's kind of OK for what it is, but west and north from Pompton Plains it's nice and open, and you have a number of options to make a loop of your preferred length.

Probably the closest open road will be the Alpine ride described earlier, which can be extended all the way to Nyack or beyond depending on your ambition. Otherwise, I'd "zone skip" using Metro North so you can spend most of the ride on the nicer, more open hillier roads I described earlier.

And then over the Tappan Zee and down the east side of the Hudson on the way back?

Definitely not. The Tappan Zee Bridge isn't open to bicycles, nor would you want to ride it if it were. You're only two Hudson crossings are the GW and Bear Mtn Bridges, roughly 45 miles apart, which is why the Bear mtn ride is always a century.

You had asked for hills, which is why I suggester the train to Peeksville, then you could ride to Bear Mtn, and come down the west side back to the GW. That can be a nice ride for you, but once you cross the river and start south, you're committed to completing the ride.

This is why I like using Metro North. I can rail past the close-in burbs, do a nice loop, and have plenty of choices for where to end, going longer if I wish, or bailing to the nearest station if necessary.

I find the ride back from Bear Mt on the west side to be something of a chore. It isn't great riding, the towns are a lot uglier than you'd think on the river because they were basically industrial towns.

Speaking of NYC bridges for hill climbing, I do a 4 (actually 5) bridges ride occasionally. I start at the Brooklyn Bridge on the Brooklyn side before it gets crowded, cross, take the Manhattan bridge back to Bklyn, then ride up to the 59th St bridge, then down to the Williamsburg Bridge back to Brooklyn. I vary the order sometimes. The 5th bridge is the Pulaski bridge between Bkln and Queens. That bridge has a new bike lane. It gets some climbing in without having to leave the immediate vicinity of Brooklyn. The bridges themselves are easy enough that you never leave the big ring, but still a little of a hill workout.

The most daunting in Manhattan is Fort George Hill, uptown, the climb from Nagle and Dyckman up. About 150 feet climbing @ a 9% grade.

Riverdale in the Bronx has a couple of good climbs from Broadway west.

New Jersey close to the GWB as well as the ferries from Manhattan is very hilly, the southern extension of the Palisades. From Jersey City north are a couple dozen ~100 foot climbs on either side (west or east) of the north-south running Palisades, this is all in built-up territory. Once north of the bridge, within the park, you have Alpine hill at about 425 and 6%. North of there is the climb from Piermont to the former Nike missile base in Orangeburg, about 650 feet at 7%. Bear of course about 1250 at 5%. These, though, are rather far from the city.

There are a couple of doozies if you know where to look. Bulls Ferry Road in Hudson County, and Edgewater Road (also known as Oxen Hill) in Bergen County, are 18% and 12% respectively, climbing the east side of the Jersey palisades up from the Hudson and in view of the city.

Lots of folks practice hill climbs in Prospect Park in Brooklyn. It's a rather short hill, but steep. Climb it ten times and you'll be ready for a beer!