My wife and I have a goal to visit all 50 states together before we're 50, we just got a few pockets + Alaska left to knock out and plenty of time to do it Last fall we went up to Seattle (met a bunch of awesome TSers) and wound our way down to San Francisco. It was a fantastic trip.

Sometime in May, June or July we're going to knock out New England. She has some family in Toronto, so we're going to fly up visit them first for a day or 2, and then head up to Montreal and cross down from there so we can easily hit VT and NH. Then we'll just pop into the bottom corner of ME to check it off and head down to Boston. We'll probably spend a couple of days in Boston. Then through RI and end up in CT and fly home from there. The route below is almost exactly as long and far as from Seattle to San Francisco, so that's kind of our time model.

Questions:

How hard is it ($$) to rent a car in Canada with the final destination in the USA? Is that a big deal, or pretty standard? Is it easier to train or bus or something across the border and then rent a car?

Anything truly amazing to see between Toronto and Montreal? We're thinking about taking the train between those cities, but I wouldn't want to miss something special.

Below is a rough line of how we want to go. Anyone living in or near those areas: what are some things worth seeing? Anything worthy of a detour?

And our most important question... FOOD! I'm sure in Toronto we'll be eating with her family mostly, but elsewhere is there something we've got to try? Who has the best Poutine??? Best Lobstah roll in New England? Etc. We want regional type food. Not just the best steak or something. Thanks in advance for ideas! If anyone wants to meet up for dinner in one of those places, I'm sure we'd treat

 

Now I know why you don't have kids...

Have a great trip Steve.

 

I can help with some of your questions.....

There is not much too amazing to see between Toronto and Montreal..there are places like the thousand Islands that are nice to see but certainly nothing too note worthy.

As for food in Toronto and Montreal, that I can help with.

In Toronto there are a limitless number of amazing places to eat...However, save the Poutine until you get to Montreal. la banquise in Montreal has the best Poutine in the world...and that is not an exaggeration.

In Toronto, everything is sectioned off into different areas.
The main areas being King St West, Yorkville, The Financial district, The beaches, St Clair West, Yonge and Eglinton, Danforth, Leslieville, Liberty Village, Distillery District and a few other places. It all depends on what type of person you are. Areas like King St West is the most "New and Trendy" with millions of amazing restaurants home to top chefs. Yorkville is Torontos "old money" area with some wonderful high end dining experiences. Leslieville is one of those areas that is considered "up and coming" but has seen a massive boom in top notch places to eat..

Montreal is home to some great places as well. For anyone visiting, a trip to the old Port is a must. Lots of character and tons of great places to enjoy the evening.

I am happy to make up a little "map" and suggest some places to check out and enjoy a meal

 

If you come to Boston you better PM me!!

 

We'll definitely be going to Boston, and I'll definitely PM you!

And thanks acrides, I especially like the food info - that's always a huge part of our traveling. I'd really appreciate your map offer. It's always hard looking around online for ideas - most websites have advertising agendas. It's much better to talk to people who really know what's good!

 

If you care enough to see them, our parliament buildings are in Ottawa. Other than that, Kingston is nice, but probably not worth the stop in between. If you do head up towards Ottawa, I'd strongly suggest doing some rafting at that time of year for a good time. I've gone with Owl Rafting before and it's a great thrill.

While in Toronto I'd recommend checking out Scaramouche for food. It's owned by a friend of the family and has an extremely good reputation throughout the city.

It should be no harder to rent a car in Canada than it is in the states, and crossing the border is fine, but having the final destination in the US will no doubt cost a substantial amount more.

 

Are you opposed to driving it? I've driven a similar trip over the course of two different trips. You can make it a max of about four hours between stops of you want. Also, Buffalo is close to Toronto. You can visit Anchor Bar (inventor of the wing), then see Niagara Falls, then cross the border and head to Toronto. It sounds like its going to be an awesome trip. All those cities sound like fun. I'll leave the suggestions to the locals, but I have some for Boston if you want. Some other fun stuff on the war back from Boston when driving, like the place that invented the burger, great pizza, etc.

 

Esthetique, thanks for those suggestions. I checked out the site and menu for that restaurant and it has me drooling! I think my wife figured out we could cross the border on Amtrak and then rent a car when we're back stateside. Insane drop-off fees were the primary concern. One rental place in Seattle wanted to charge us like $500 extra to drop it in San Francisco!

Charles, we've been to Toronto, Buffalo and Niagara Falls and stuff a few times. We're just hitting that specific area because D wants to visit her family and we decided since we're up there we'll make a trip of it.

We were debating coming back across to Buffalo, crossing NY and going into VT and NH that way, but D and I feel we can't go to VT without going to Ben & Jerry's which is further north in VT, so we thought let's go up through Montreal and then down. May as well see a bit more of Canada while we're up there! I'm feeling a bit more confident lately taking time off, and so I may make it even a little more extensive.

We can definitely talk about Boston next time we meet up. You know I respect your travel, food and food-travel advice!

 

Renting a car and dropping it in the US is a couple hundred extra. 300, maybe? Not exactly sure. Driving a rental across the border is the best, and a non-issue. Bus is the worst. Train is ... wait what? They still make those? It's not the 1900s anymore!

As was mentioned, between Toronto and Montreal the only worthy thing is the Thousand Islands area, but hardly worth the rest of the boring drive.

Careful in Ontario, anything over 50kph over the limit and they'll impound the car on the spot. Same in Quebec for 60kph over on the highway, 40 or 50kph in town.

Leaving Montreal, I'd take route 2 in VT, which jumps from island to island. It's quite picturesque, certainly more than the 89. Then You could do a detour by Stowe, the 108 close to Sumggler's Notch is an interesting super narrow twisty road sided by cliffs, and you can stop and go hiking if that's your thing.
Also, you can check out Lake Placid and the Olympics site on the NY side (if you have any interest in it), then ferry (5-10min) across lake Champlain at Port Henry and head to Stowe/Smuggler's Notch from there.

The Ben&Jerry factory is somewhere around there, rode by more than once. Also, Burton snowboards factory.

Then, once in NH I'd take Kancamagus Highway to Mt Washington and drive up/down. If you're lucky and it's sunny, it'll be pretty. If it's bad weather you'll wonder on WTF planet you are. Neat either way. That's Bretton Woods area, if you enjoy nerding out on history like I do.

Food! Montreal!
La Banquise - the most famous late night poutine place. Kind of a cliche for visiting friends, but don't think the food is subpar for a second. It's the real deal.
Frite Alors - they're a nice alternative (I actually prefer them to La Banquise), and have 3-4 locations. A chain (sort of), but I absolutely love their poutines!
Romado's - a portuguese chicken place. I swear they sprinkle crack on that chicken it's so delicious! I haven't been in a while since I don't work in the area anymore but I'll double check, make sure they haven't gone down in deliciousness since. It's mostly a take-out place though. So grab your chicken goodies and picnic on Mt Royal parc 2 blocks away. It's pleasant.
Schwartz's - smoked meat, another Montreal classic. Doesn't do all that much for me, but it's not bad by any stretch of the imagination. Just not worth the hype (and line-up) IMO.
St Viateur Bagel - perfect after a night out drinking, preferably at Dieu Du Ciel (beer, beer and beer)
Grumman 78 - The taco truck! Usually hangs out at events. Have not been disappointed.
Au Pied de Cochon - I haven't been (don't know how that happened), but from reputation it is a must-do. Very rich and delicious.
Tri Express - exceptional sushi place, from reputation.
Aux Vivres - it's a vegan restaurant worth trying if you're curious about the whole vegan thing. I've eaten there more than once and it's definitely surprising, in a good way.
Qing Hua Dumplings - they're awesome ... but not sure it's what you're after when in Montreal?
Buns - again, great burgers, but not sure they're special enough to warrant going. If you're on St Laurent and feeling hungry, then yes.
Fancy places I'm less familiar with ... I live here! Garde Manger is said to be top notch.
Also heard great things about l'Orignal which is the building next door in Old Montreal. The same guys have a lunch place called Gros Jambon, a supposedly delicious burger joint that I shamelessly have not been to yet!
I don't know if you can still do sugar shacks when you'll be around. But if you can, Sucrerie de la Montagne was pretty damn authentic. It's an hour from Montreal, was on No Reservations QC too!
I'm sure I'm forgetting stuff ... but there's only so many meals one can have! How long are you staying?

Boston food (was there last weekend), for the love of God do not do the Durgin Park or Union Oyster House tourist traps. You will regret it.
No.9 Park was warmly recommended (didn't go), as well as Fireplace grill for brunch. Went to Neptune Oyster and couldn't eat (short on time) ... was bummed as it looked phenomenal. We're planning on going back just for those 2 places we missed! Also, we did enjoy a short drive to Nantasket, seeing the city across the "bay", and restaurants with names such as The Clam Box.

That's all I got for now.

PM me for moar info, I can dig up some maps if you want as well.

 

Wow, thanks! I really appreciate the driving route suggestions, that sounds excellent.

As for taking a train, we think it's fun But if driving across is that easy, that may be the way we go.