If you want to add a little drive after Ben & Jerry’s, you could go up I-91 to Haskell Free Library & Opera House & be inside a building & have a foot in each country at the same time.
Not so out of the way is an amazing little chocolatier in Saint-Jean-sur-Richelieu.
Also, Hint: the smaller crossings are usually much faster than I-87 or I-89. The westernmost one in VT I had to knock on the glass to get them to come out as I was the only one crossing there, no line at all.
Strip down to parka and Mukluks? 
If your family likes science/animals/dinosaurs, McGill’s Redpath Museum is a good (and free) choice.
I second the Biodome and the subway (called the “metro” here.)
I live in Montreal and could maybe show you around a bit. 
I’ve done that with another board member’s family.
And thanks for the mention, Leaffan.
The Haskell Library is an hour and a half in roughly the wrong direction from Ben and Jerry’s.
If you’re headed to Montreal, you’ve got two basic routes; up 91 into Canada, or over and up on 89.
Cool things along those routes:
St. Johnsbury:
Either way, you’ll be hitting St. Johnsbury (and either going north from there, or heading south on 91 or west on Rts. 2 or 15 to get to 89).
St. Johnsbury used to be a thriving town with some real wealth due to the Fairbanks Scales company. It’s in somewhat of a sad state now, but there are still some beautiful homes, a well-regarded academy, and some cultural treasures due to the legacy of the Fairbanks family:
http://www.fairbanksmuseum.org/ <- A very cool natural history museum with origins and exhibits from the end of the 1800s.
https://www.stjathenaeum.org/ <- Public library and art gallery, with some very unique architecture, and an art collection curated/collected (again) at the end of the 1800s.
Heading North up 91:
A slight detour off the highway will take you to Glover VT, where you will find:
http://parkerpie.com/ <- Great beer selection and pizza, tucked in the back of a typical rural general store. This place is far enough off the beaten path (and you’ll be in a pretty rural/empty part of VT) that it still feels like a true ‘local’ experience, while being actually reliably tasty.
http://breadandpuppet.org/ <- Bread and Puppet Theater is a counter-culture/performance art organization with roots in the 60s. If you’re at all interested in art as protest, puppetry, and things of that nature, try to catch a performance, or just go to the museum.
http://museumofeverydaylife.org/ <- Looks like a small falling-down barn on the side of the road, previous exhibits have included “The toothbrush” “The pencil” and “dust.”
Kind of equally out-of-the-way for all routes to Montreal is:
http://hillfarmstead.com/ <- If you’re beer people, you may have heard of Hill Farmstead, which has won all sorts of acclaim/awards. Their beer is awesome, but I have yet to visit the brewery. From what I understand, it can be a bit of a $#%!-show with long lines, depending on the weather/time of day. If you like making beer pilgrimages, it’s worth it, otherwise, you can find their beer on tap all over the state.
Rt 2W to Rt 15W to 100S to I89:
http://lostnationbrewing.com/ <- great beer, and really tasty outdoor BBQ. It’s one of my favorite places to go in the summer (I’ll often drive out to a swimming hole near there, and then do beer/bbq afterwards).
This route takes you to the Ben and Jerry’s factory. Do it if it excites you, but I must admit that any of the other places/options on this list are more interesting/tasty excursions IMHO (though that may be because I grew up here).
Rt 2W to I89:
Redirecting... <- Really spectacular baked goods, tasty dinners, and an owner/baker who is certainly a “character”. This place has been written up in the NY Times (albeit many years ago); the owner is a NYC fugitive who came up to VT in the 70s and opened this bakery and has been serving food in this rural cafe/bakery ever since. Also one of my favorites.
http://www.thecountrybookshop.com/ <- If you like stacks and stacks and piles and shelves of old books of all sorts, go here.
POSITIVE PIE PLAINFIELD, VT | HOME <- Good pizza/beer right across the way from afore-mentioned bookstore.
(This route also gets you to Ben and Jerry’s, btw).
. . . those are all of the “off-the-beaten-path” places that I can think of this morning that might be worth consideration. If you take either of the I89 routes, you’ll pass through Waterbury and Burlington, and I can happily give you recommendations for things in/around here if you’d like. (Or, Stowe, which is on the 2/15/100/89 route, or Montpelier, which is on the 2/89 route). Or, if there are specific kinds of things you’d like to do/eat/see, I can make some other suggestions.
I can make Montreal recommendations too, but there are probably others better qualified than I to do that.
Also, Montreal is a big city where it can sometimes be difficult to drive and find parking (not to mention the potholes) so it may be best to drive to the hotel or wherever you’re staying, and take public transit elsewhere (we have a good public transit system.)
if you are in Quebec City, I strongly recommend dinner at Aux Anciens Canadiens - traditional Quebec food.
Thank you for the experienced information! I would like suggestion for shorter hikes in the Breton Woods area, please.
This, absolutely this. Take some time to explore New Hampshire. I took a ride up Mount Washington last year on the Cog Railway, which was fascinating to me. The engine pushes the car up the rails to the summit, but it is not actually coupled to the car. The car has its own braking system for the return trip, operated by two brakemen.
There’s also theConway Scenic Railroad that offers a five hour round trip through the mountains to Crawford Notch, among others. I’ve only taken the trip to Crawford Notch, so that’s the only one I can recommend.
The North Conway area is just south of Mount Washington, and there are all kinds of shops in the downtown area, as well as outlet stores in the outskirts, all of it tax free, as New Hampshire does not have a sales tax (they do, however, have a meal tax when you eat out at restaurants).
Nearby in Naples, Maine, you can take a river cruise on the Songo River Queen, which goes through numerous locks as it travels down river.
No matter which city you go to in Québec, you’ve got about a four hour drive ahead of you (from Conway), not counting any waits at the border.
By the way, Portland to Conway is only an hour and a half of driving; it’s two and a half hours from Boston, with traffic out of Boston being a far greater variable than out of Portland—seriously, Massachusetts traffic and Maine traffic are not even comparable. Get your elderly in-laws to fly into Portland, and let them enjoy a stress-free, scenic ride through Western Maine to get to New Hampshire.
And don’t neglect the Portland waterfront, either. If you fly into Portland, spend a day there and just meander along the waterfront. Large ocean liners frequently berth there. The city itself has a very “indie” vibe to it with a lot of independent shops. It’s a very walkable downtown, so just plan to park your car in a garage for the day.
I’m not trying to discourage the OP from going to Canada, mind you, but the location she’s going to is far nicer than she seems to think. The only attraction I remember much from Québec City is La Citadelle. To my young (at the time) mind, it seemed an absolutely massive fortress. It’s one thing I’d love to see again, so I’d definitely give it a recommendation. I’ve never been to Montréal so I can’t say much about it.
And seconded. I had almost forgotten about that place. I was just a young whipper-snapper when I went, but when I saw the photos on the site, I remembered the place.
Just hang out and see what Quebec is like. Go to yard sales and talk to people. Make sure they know you are American, or they might hold you in (justifiable) contempt for being Canadians who can’t be bothered learning the second language.
Quebec drivers are notoriously awful (selfish, rude, impatient), worse than Boston or even Mexico. Drive very, very attentively, and be ready for anything.
Touristic sites are touristic sites, pretty interchangeable, but what makes Quebec different and memorable is the Quebecers who live and feel at home there.
I remember driving in Québec as a teenager. Now like a typical teenage boy, I liked driving fast. But I was not prepared for the level of fast that rural Québécois are used to on pot-hole filled back roads. The speed limit signs may be in kilometers per hour, but they drive as if they were in miles per hour. They might slow down to five or ten kilometers above the speed limit if it is snowing, but they don’t seem to care one bit if the car is fishtailing all the way down the road in the middle of a blizzard.:eek:
Also, one thing you must definitely watch for in Québec that is different than any state I’ve ever driven in in the U.S. If there is an uphill passing lane on a rural road, often the downhill side may use it too, so check twice before you pass that truck that moved to the slow lane.
I’ve always been fascinated by, and have never been to, the Eye of Québec (Manicouagan Reservoir). It can be seen from space – here’s a picture with the correct north-south orientation. But it’s a 9:30(!) drive from Québec City (map), and 3h farther if from Montreal.
Alas, much too far?
I came in here to make this very suggestion! If you go, have the maple sugar pie. It is among the most amazing desserts you will ever taste!
I’ve always thought D18 is a man of good taste.
I second the Jazzfest. And we have at least one Ben & Jerry’s here (on McGill College just below Ste. Catherine St. Whatever you do, stay away from Sherbrooke St. near McGill.
What’s the problem with Sherbooke St?
The problem with that part of Sherbrooke street: a whole lot of construction that’s difficult to navigate.
Looks like the desserts are anything you might like as long as it’s maple :). OK, the chocolate tart and the sorbet might not be maple-based but I’m not betting the rent, LOL.
Funny enough, the only Quebecois food I’ve ever eaten is poutine (all our students knew of that) and pouding chaumeur (all of the students looked at that recipe like I’d lost my mind).
Off to read the rest of the thread…
Here’s a dumb question: how much difficulty will the family have getting around in Quebec, language-wise? I speak a decent amount of French (if with questionable grammar and pronunciation), but nobody else speaks anything beyond “merci” and “bonjour”. Our students obviously always spoke a fair bit of English but this was after (I presume) learning it in school and 2 years of college specializing in languages.
Re big city / transit: yeah, we’re from DC and I’ve spent a fair bit of time in NYC and won’t voluntarily take a car into either! My son would be thrilled to use the metro (though depending on his work schedule we might basically have to drop him at the airport on our way into the city the first day).
I don’t know what our schedule will be like: we’re planning to arrive late-ish on the Monday, and somewhere in there will get together with one of our students who now lives in Montreal. But if time permits, we’d certainly love to get together with any local Dopers!
Like I said, the area we’re visiting isn’t the issue, I’m just grumbling about its general inconvenience to many of the attendees. For us, it’s as good as my alternate suggestion (Florida) aside from the expense and the fact that it makes some specific logistics (e.g. group meals) tougher and more expensive. And we’re leveraging it to visit Quebec and friends there.
And we are most likely going to come back through Maine - the shortest driving distance actually suggests a slightly different route but we’ve been to Portland a number of times and love it, and I’d like to see more of the coastal area. We’re semi-seriously thinking of going around via New Brunswick just to get on I-95 at the border so I can say I’ve been to both ends 
(and therefore every inch of it except the bit between New York City and Boston).
Language won’t be an issue in Montreal. Pretty much everyone in Montreal is bilingual.
Outside of Montreal it’s touchy, especially near Quebec City. You SHOULD be OK with hotel clerks and waitstaff, but not guaranteed. The average guy or gal on the street probably won’t speak much English.
Do encourage others to at least use “merci” and “bonjour.” It is appreciated.
The Montreal Jazz Festival is awesome if you like music. It’s not all jazz.
I have eaten there. It’s very good but a bit of a cliché.
Visit Ile d’Orleans, the island outside Quebec city. It is not very developed and mostly farms, but there is a killer frozen custard ice cream shop with an option for maple dip. There are also wineries and cideries to visit and a several nice inns and restaurants.
As for language, in all the shops, hotels, and restaurants, people will speak English. Some people do not speak English or don’t speak it well, but those aren’t the people you will be meeting as a tourist.
Quebec has a minor league professional baseball team. We saw them play a New York team when we were there. If you really love baseball, this is a great small-town kind of experience. (They are an independent league, not part of the MLB farm club system.)
We were in Quebec during a county fair, and spent a couple of hours there. Nothing out of ordinary but if you like to do what locals do instead of going to tourist sites, it’s fun.
Here are my photos from our two
trips to Montreal and Quebec.
IIRC you are in my general area so my wife and I would be happy to meet you and tell you how much we’ve enjoyed it there.