I’ve been driving in and around this goddamn city for 10 years now, which makes me an expert.
(Note: My definition of “highway” and “parkway” has been parsed such that “parkway” means [mostly] roads that call themselves parkways while “highway” means every other road aside from that that I’ve deemed not a parkway but, in fact, a highway. There are, indeed, some roads in the tri-state area that call themselves “parkways” but aren’t actually parkways, like Pelham Parkway. I have not included those roads. There are also roads that you may consider to be highways but that aren’t actually highways. If you think I have erred in any of these determinations please email me at email@example.com.)
1. Interstate 86/New York State Route 17
This, for my money, is the tri-state area’s best-kept secret, a highway that feeds into the city, isn’t boring to drive, and also happens to be beautiful 95 percent of the time you are driving it. One other good thing? On many maps, it doesn’t show up as a proper highway for the last 150 miles or so, before it runs into the New York State Thruway. But it is, if you can handle a few stretches at 55 mph. That also means you’re reasonably likely to find yourself like I did on Wednesday around 4:30 p.m.: Just you and the glorious road for miles, which almost never happens with every other other road on this list.
2. Palisades Interstate Parkway
A gorgeous drive, and truck-free, and gets you to the good parts of Jersey and New York.
3. Taconic State Parkway
See above, except without Jersey.
4. FDR Drive
When it’s not clogged with traffic, which is more often than you’d think, driving the FDR feels like a video game.
5. Interstate 78
Of all of your options leaving NYC to get to points west via New Jersey, I-78 is the best. Emerging from the Holland Tunnel, it feels like a highway version of Midtown Direct NJ Transit service. Clean and easy.
6. Henry Hudson Parkway
The Hudson deserves this spot for the Henry Hudson Bridge alone.
7. Ocean Parkway (Long Island)
I’ve never actually driven this but I’m told by Michael Ballaban, Jalopnik’s Deputy Editor, that Ocean Parkway is “the perfect road if you want to relax—long and straight beaches on both sides with no traffic.”
8. Bronx River Parkway
The Bronx River is not one for getting speedily north, but it’s fascinating as a look into motoring history, as it was the first limited-access highway built in the United States. And it shows, with a lot of strange exits that display just how much they were making it up as they went along.
9. Sprain Brook Parkway
As far as parkways that are actually nice to drive on in Westchester, the Sprain is tops, probably because it’s the newest.
10. Interstate 84
When it comes in driving to Connecticut, it could be worse!
11. Interstate 478, Brooklyn-Battery Tunnel
Fun, for being a tunnel. You leave nowhere Brooklyn, end up in the center of the world. I mean the Financial District.
12. Interstate 87
I-87 is long and has very distinct parts, some of them very bad, like the part known as the Major Deegan Expressway. You also have to pay for it on the stretch from Westchester County to Albany. But! It is the road to Montreal.
13. Hutchinson River Parkway
The Hutch is almost always the best way by car to get from Westchester to any point on Long Island, Queens or Brooklyn. It is also frequently stuffed with cars and the scene of many an accident, because it was narrowly constructed and the exits tend to be short. Even with these faults, driving it is usually tolerable, and sometimes even pleasant.
14. Meadowbrook State Parkway
I have no comment.
15. Interstate 280
You can find one of the more dramatic hills on any tri-state interstate on I-280, and it’s fun to drive up and down. Seeing 280 is also a sight for sore eyes after you’ve driven the length of 80 through Pennsylvania; 280, at that point, is your beacon of hope, with your trip nearly finished and your work complete.
16. Northern State Parkway
Better than the Southern State.
17. Interstate 684
After you’ve emerged from the madness that is a drive up the Hutch, you hit 684 and its three lanes, and it’s nice to be able to stretch your legs again.
18. Harlem River Drive
This is, if nothing else, an important reminder that the Harlem River and East River are two different things. Also, the ramp up to the George Washington Bridge is cool.
19. Seaford–Oyster Bay Expressway
Seems fine. It’s the best route to get to Bethpage.
20. Sunken Meadow State Parkway
The access road for a lovely park. Try going if you have a chance.
21. Interstate 695
Eh. Ranked here because it’s very short, meaning your drive on the 695 will suck less by virtue of being short.
22. Interstate 678, Van Wyck Expressway
On paper, I love the Van Wyck, since it’s a direct connection to JFK, and it’s got that thing where you can explain to an outsider how it’s been mispronounced all these years, and is still mispronounced to this day, thus making you seem like an enlightened one. In practice though, it’s usually—I mean almost always—snarled with traffic, and, in practice, pedants about pronunciation are among the most irritating people on Earth.
23. Interstate 878
See the entry above for I-678.
24. Sagtikos State Parkway
25. Jackie Robinson Parkway
This feels like a secret way out of the city for car owners, since you catch it in kind of the middle-of-nowhere Brooklyn, and it whisks you to the Grand Central Parkway and points east in no time. It’s also named after one of our greatest humans! What’s not to love? Traffic, for one, and the fact that getting to it and leaving it sucks ass.
26. Merritt Parkway
On its day, among the prettiest drives in all of New England. But since it’s one of only two major arteries to go through lower Connecticut from NYC, it is frequently not its day.
27. Garden State Parkway
The Garden State pretends like it’s better than other roads, because, after all, there’s only one Garden State Parkway, and also people from New Jersey pretend like it’s special, a higher class of travel than, say, the New Jersey Turnpike, or, God forbid, an interstate or a state route. Do not be fooled.
28. Interstate 80
I’ve driven I-80 too much at this point, and I hate it to the extent that I in fact might be overcorrecting on its positioning in this ranking here, to account for my bias. It’s not really I-80's fault though. I-80 deserves to be loved.
29. Grand Central Parkway
Like a lot of roads on this list, the Grand Central is, usually, just fine, and you get to drive by some cool shit on it, like the Queens Museum, and Flushing Meadows-Corona Park, but the interchanges to get onto the LIE from and to the Grand Central are among the most irritating and baffling in the city; heavy point deduction.
30. Wantagh State Parkway
Sure. Of note: It takes you to the beach.
31. New Jersey Route 3
Not always terrible, and you get to see Giants Stadium.
32. New York State Route 440, West Shore Expressway
This is useful if you’ve entered the city through the Outerbridge Crossing (named, fun fact, for Eugenius Harvey Outerbridge), but if you’re entering the city through the Outerbridge Crossing, that usually means the other crossings are backed up, and/or you’ve decided to go to Staten Island. Neither of those are, in other words, optimal situations, though Staten Island is a beautiful place.
33. Interstate 95, New England Thruway
The New York section is fine, but the Connecticut section is a depressing jaunt though cities like Stamford, punctuated only by the occasional stop, since traffic always seems to be bad on the New England Thruway, and it’s also seemingly been under construction its entire existence. While you’re stopping, you can look over and see Metro-North trains flying by, and the people inside them, who are happier than you, because they’re not sitting on I-95.
34. Belt Parkway
Looking at the water is nice, and looking at the ships, and driving under the Verrazano-Narrows Bridge is incredibly cool. You’ll have a lot of time to look, too, since, when the Belt Parkway isn’t a parking lot, it’s under construction, and when it’s not under construction there are potholes that will eat your car.
35. Cross Island Parkway
Very similar to the Clearview both geographically and in spirit, though better because trucks are not allowed and it’s an alternate way to get to JFK if the Van Wyck is fucked. The Van Wyck is usually fucked.
36. Interstate 295, Clearview Expressway
Useful for getting places, and only then sometimes, but that’s about it. Deeply uninspiring.
37. Interstate 95, New Jersey Turnpike
It’s very large. If you’re on the Turnpike, it means you’re going somewhere else, like probably Philly, which means you’ll be spending most of your ride wondering when this depressing march through the heart of Jersey is going to end. You’ll do this while stopping at the Turnpike’s service plazas, which are jam-packed full of slobs like you and me. Everyone there is either pissing, shitting, eating, drinking, smoking, or waiting in line for gas, frequently all at the same time. It’s total hell.
38. Interstate 278, Brooklyn-Queens Expressway
The BQE has, for my money, the best view on any major road in the city, as you drive north in Brooklyn Heights and Lower Manhattan is beaming across the river, imposing and majestic. It also, though, has the same problem that afflicts the Belt Parkway, in that it’s all-too-often a parking lot, or filled with tire-destroying potholes, or both. I want to love the BQE, but it doesn’t have the capacity to love me back.
39. Southern State Parkway
Mainly bad, though it can get you places.
40. U.S. Route 46
Not even as good as the Southern State Parkway.
41. Interstate 287, Cross-Westchester Expressway
Great if you like driving alongside families motoring sensibly while packs of deranged maniacs roar by, wanting to either show off or go home, because their lives are filled with quiet desperation.
42. New Jersey Route 17
43. Korean War Veterans Parkway
Staten Island’s version of the Jackie Robinson.
44. Saw Mill River Parkway
The worst north-south parkway in Westchester County, ostensibly offering a “parkway” experience but, then, forcing you to stop at traffic lights. No.
45. Cross County Parkway
Joe Girardi stopped to help a motorist on the Cross County hours after winning the freakin’ World Series. This is the only good thing that’s ever happened on the Cross County Parkway.
46. West Side Highway
It doesn’t even belong on this list, really, since despite calling itself a “highway” it is in fact just a normal road with traffic lights, albeit a little wider than normal roads. The West Side Highway is a pretender that is fooling no one.
47. Interstate 495, Long Island Expressway
48. Mosholu Parkway
It’s fun to say out loud, sure.
49. Interstate 895, Sheridan Expressway
Rightfully on track to being destroyed.
50. New Jersey Route 4
It will make you question why we are here at all.
51. Cross Bronx Expressway
One time when I was in college in the early aughts and I knew nothing, I was driving home to Ohio from my then-girlfriend’s undergrad in Massachusetts and decided, because I was a big dumb idiot, to take I-95 through the Bronx so I could “see” New York City (I had never been at that point in life.) I ended up sitting in traffic on the Cross Bronx for three hours and seeing nothing. Chalking the traffic up to “things that happen in the big city,” I didn’t think much of it. When I moved here a few years later, I realized the true depth of my error. Never take the Cross Bronx under any circumstances. Save yourself.
Back around 1960, Moses used the argument that the neighborhood now known as SoHo—today some of the most valuable urban real estate in the country, if not the world—was a downtrodden area that would be the perfect place to host a highway. It was a post-industrial slum beset by fires, dubbed “Hell’s 100 acres” by those pushing urban renewal at the time. But a feisty and eclectic group of New Yorkers rose up in rebellion, aghast that anyone would want to lay waste to homes and businesses for concrete, asphalt, and steel. Fifty years later, it would be hard to find anyone who isn’t glad that they did.