It's pretty simple, really: ride a bus overnight, spend the day walking an ad-hoc half-marathon, and then take another overnight bus ride to get home. It’s really not that difficult. With the goal of making the experience suck as little as possible for anyone else who wants to give it a try, this is how I do it.
Greyhound runs a lot of buses between Toronto and New York, so this is the trip I prefer. I look for ones that arrive around 6am – I’m no morning person, but they're usually late. This means an early-evening departure, probably around 7 or 8pm, and being at the Bay Street terminal about an hour early to make sure that I get a decent seat. With a little bit of luck I can be stepping out onto Eighth and Forty-Second street in Manhattan just twelve hours after locking my front door.
Have your ticket and ID ready when getting on the bus, and since this run will be crossing the border “ID” means your passport. You'll probably have two or three tickets to get you to NYC, but this driver will only take the Toronto-Buffalo one. The drivers will change in Buffalo, and sometimes in Syracuse, and each one will need the ticket for their individual part of the trip. You'll be boarding an American bus, which is distinguished by its 5-digit bus number and ADA-compliant midships wheelchair door; Canadian buses have 4-digit numbers and poor accessibility. All of the buses on the cleverly-branded "NEON" – NEw york-ONtario – route will have household electrical outlets and spotty low-bandwidth Wifi.
The first hurdle on the bus – once embarked and underway, which often requires a three-point turn – is crossing the border. This is typically around the 2h30 mark, and always involves a fair bit of waiting. The bus can't idle its engine while in the customs bay, so the HVAC system is shut down for extra-special bonus points. To clear customs you'll get off and walk all of your baggage though the building, and when you're done you return to the same seat you started with.
Being Canadian is the next best thing to actually having an American passport. We don’t get photographed, fingerprinted, or charged a processing fee. But being welcomed will usually mean passing luggage through an X-ray and occasionally involves dogs. I've taken the bus to NYC six times; twice there were sniffer dogs looking for banned agricultural products, and once for drugs. Note also that Greyhound's own policies ban alcohol or pointy things on their buses. I've been searched once going from Ottawa to Toronto, and seen another inspection station being used in Chicago.
I've almost always crossed the border at Buffalo. The inspection station has no amenities at all, but the bus station is about fifteen minutes from the border crossing, and has an actual Tim Hortons in it these days. Washrooms are capacious and located at the far left end of the terminal, but the doorways are badly designed. Still, it's hard to be picky: Toronto's bus terminal is very nearly the worst one I've ever been in. Omaha beats it, since it's surrounded by a prison, but not by much.
Once back underway there will be a couple more rest stops, typically about every 2h30-3h apart, even if they din’t show on the itinerary. Not much will be open during the middle of the night, but there's usually fast food, vending machines, or a convenience store. And washrooms, of course, so this is one of the many times that being in the front of the bus pays off.
The last rest stop is deceiving. You're heading downhill, the sun is either up or rising, there are signs of civilization up ahead, and a difficult night seems to be at an end at last. Don't be fooled. There's still another hundred miles to go. Go back to sleep.
Actually arriving in New York is incredible. It happens almost without warning. There are a few low industrial parks, a few trees, and a glimpse of the city skyline. Then the bus is through the tunnel, takes a couple of turns, and you're plunged back into the underground of the terminal. You've arrived at the Port Authority complex and are now in midtown Manhattan.
The rarely-cheaper Megabus stops on the side of the road near Penn Station. I took Megabus once and these days don't even bother checking their ticket availability. The sprawling Port Authority complex, with shops, washrooms, and an actual building, adds far more value than the occasional few dollars that the double-decker saves. The Hound even leaves from the same part of the terminal that it arrives at, so look around and remember your route as you head out of the building.
Right off the bus there are three priorities: decent food, a clean restroom, and restoring mobility – in no particular order. It's hard to give advice here, but going South or East generally works out best. South is Penn Station, the New Yorker hotel, and 34th street. East is 42nd Street, Times Square and all kinds of restaurants, but few of which will be open at this hour. There's a popular pastry/coffee shop a bit north on 8th, but it's busy and I can't vouch for washroom availability. West is the Hudson river, and not the pretty part.
Despite its reputation, New York City isn't all that active a place very early on a Saturday morning. This is my favourite time to be in The City, watching it as it wakes up, so I try not to linger too much over breakfast. Many of the minor east-west streets will have loading docks and interesting things happening, while the tonier avenues get the stroller-and-jogger crowd. And of course Grand Central and Central Park offer their own mix of people and amenities.
Pacing and judgement are key. The day is going to be too long to go full-on the entire time, but the opportunities are too fleeting not to. Resolving that contradiction – to always be working, even when taking breaks – has been the key to my most successful days. I prefer to have goals but not expectations, to have plans that are open to change, and stay receptive to the inevitable unexpected opportunities. After all, this is New York.
There's really no shortage of things to do. My bad-weather contingency plan is usually to go to the Museum of Modern Art, but the Met is pretty decent even if it is a fair bit farther from the bus station. The High Line is usually filled with tourists, so if that's on the list then head there first. It's best if it's admired quickly and then left.
By late-morning Manhattan is usually becoming a bit too much for me, so I grab an early lunch and head to the beach. Spending an hour riding the D, N, F, or Q lines gives some much-needed down time, as well as a few photographic opportunities of its own, and those four trains all end up in Coney Island.
Coney is many things – an actual island not being one of them – and is the place to go for its boardwalk, beach, amusement parks, and stores. The main drag along Surf Avenue is as fascinating and varied as anything in Manhattan, being something of a hybrid of Lundy Lane in Niagara Falls and Kingston Road in Scarborough. It has its famous hotdog stand, which reminds me a bit of Honest Ed's, along with beach shops and other curiosities.
Even in the off-season Coney Island is an interesting place, but it comes into its own in warmer weather, especially on the first saturday of summer when there tends to be a large parade. I've been making an effort to attend on this particular weekend as a summer-starting tradition. It has invariably been a great day for beach weather, and everyone there is happy and having fun. Just don't expect to get a table in any of the local restaurants that day. Three-quarters of a million people out for a day at the beach will do that.
As the evening approaches I head back to the subway and into the city. Two good dates to know are for "Manhattanhenge": when the sun sets directly in line with the east-west streets. This is typically at the very end of May and again at the middle of July. Between these dates the sun will transit between the streets as it sets, which is almost as interesting. And don't forget to find something for dinner, because the day is almost done.
I aim for the Greyhound on the Syracuse-Buffalo-Toronto run that leaves around 10:30, but the crowd builds early, so I try to arrive over an hour beforehand. Go in through the south building, with the entrance just north of 40th Street, and head down to the lowest level. There are restrooms down the hall from where the queue forms; by this point in the day they're just slightly better than the ones on the bus, but at least the station has running water and doesn't move.
Exiting the city is done as suddenly as the arrival: a few turns, a tunnel, and New Jersey. The longest that I've ever stayed awake on the return trip was when doing this run the night before Sandy arrived, and I wanted to make sure we made it out; I later learned that the terminal shut down less than an hour after my bus got away. So barring unforeseen events the next stop will be the Gouldsboro Travel Plaza, which is a cute little truck stop in Pennsylvania. You were here just twenty hours ago.
If there are too many travellers to fit in one bus then Greyhound usually puts on extras. These will run “express”, skipping the other stations on the way to Buffalo, so don’t get too attached to the idea of seeing Syracuse or Rochester even if that’s what the schedule says. (There will still be rest stops.) Syracuse is actually a pretty decent station, with more amenities than most, while Rochester has never been more than a place where government officials check the documents of people travelling within the country. I've also been through that while waiting the night away in the Buffalo bus station, which seems to offend my Canadian sensibilities more than it does for my American fellow-travellers. Perhaps they’ve read fewer Tom Clancy books about “Papers, Please!” checks in restrictive Communist Russia than I have.
There was one time when armed American agents - redundant, I know - boarded the bus just before it crossed the border in Detroit. I was on my way home from Chicago, and the guards questioned everyone about who they were, where they were from, and where they were going. After asking some South American business travellers if they were transporting guns or large amounts of cash - “no” being the correct answer to each - they got to me. I was on a one-way ticket, having crossed into the US by car a couple of days prior, and this was enough that they took my passport with them and instructed the driver to wait. Only my passport, nobody else's. It was only a few minutes before they came back and waved us through to Canada, which was just a good frisbee-throw away, but I still wonder what that was about. Were they going to put me on a bus and deport me?
The final leg of the NYC-Toronto trip means crossing the border outside of Buffalo. Once again the driver will need to see a passport when taking your ticket, and don’t bother putting it away. The routine going into Canada also means taking all of your luggage through customs with you, but there are no dogs or x-ray machines. The difference in the architecture is also fairly striking: like the American facilities, these are essentially built like bunkers, but the steel bollards and cinder blocks are replaced by granite boulders and concrete poured in rough-hewn timber forms. We’re self-consciously naturey, us Canadians, and we do like our poured concrete.
Sometimes, after clearing Canadian customs, the passengers will spontaneously form an orderly queue while waiting to re-board the bus. That never happens on the American side.
And that, basically, is that. The bus gets into Toronto in time for a decent sunday breakfast, and late enough that our rather Protestant subway system has started running for the day. If you don’t have luggage in the cargo hold you can ask to be let out around Wellington or King on University avenue, but it’s not much further to go into the station. Toronto’s arrivals building is just across Elizabeth street from the appalling departures lounge, so if you’re being met by someone make sure they know where to find you – and that the bus is almost always late.
And of course, one last thing: the washrooms in the basement of the Toronto terminal are terrible, far too small and typically needing custodial attention. There’s an underground passage to the Atrium on Bay to the east, which has a much nicer food court and amenities, or a Tim Horton’s just west at Edward and University. Tell them I sent you - they'll have absolutely no idea what you’re talking about.