We did it about 5 yrs ago. We live in CT. Our itinerary was 3+ weeks and involved flights, but, FWIW.... here is what we did.

We drove to Burlington VT. Stopped for lunch in Great Barrington; cute town on the way. Did the bike ride along and "into" Lake Champlain. Loved it. Stayed 1 or 2 nights.

Then we drove to Montreal, spent the afternoon, (shopping and lunch, must eat at Arthur's!), and continued on to Quebec City. 3 nights there, highlight was plein aire Cirque du Soleil, and the food. Bayard IIRC. Casual.

Then we *flew* to Toronto, and from there drove to Niagara on the Lake (the charming Canadian side). Great food again Treadwelll (farm to table), and a jet boat tour of the Falls.

Then we flew (IIRC all the flights were Westjet) to Halifax from Hamilton, ON. From Halifax drove to Cape Breton, spent a few nights there. Did some hiking and whale watching and beach walking and moose spotting. Drove around the island to get to the PEI ferry. Took the car ferry to PEI. Spent a few days there. Singing sands, jumping off the bridge at Souris, touring Cavendish Park, and the home Anne of Green Gables. Loved PEI.

Drove over the PEI bridge and stayed in St. John to break up the drive and stay at a cool hotel for the kids with an indoor/outdoor slide.

On to Bay of Fundy, where we stayed in Canadian Park Svc yurts overlooking the BOF. Walked the BOF, also ziplined over the coast. Misc hikes.

The drove to Bar Harbor for a few days and hiked in Acadia. Lovely park and great little town.

Then we drove to Rockland, took a boat out to Vinalhaven, and then private transfer to our very own private lighthouse (Goose Rocks) where we stayed 2 nights. Kayaked.

Then we drove to Portland ME. Cute shopping, fabulous foodie town (Central Provisions is TDF), fun ferry system to surrounding islands.

Next we drove to Ogunquit, Maine, did he beaches, lighthouse, walked the Marginal Way, Charming. Yummy food again, Northern Union, Brix and Brine.

From there, home.

In re border crossings, easy peasy into Montreal. You need passports of course. Took very little time. Same thing when we crossed at Vancouver about 3 yrs ago. No big deal. HOWEVER you want to avoid high traffic times (google for more info)

Yeah, I would avoid American and Canadian holiday weekends.

Great info, mtn, thank you so much. I'll have to refer back to your post when we are ready to go. Sounds like you had a fabulous time.

gscience, I'll have to google Canadian holiday weekends....thank you.

Yes, we did. Happy to help if you have any lodging or other q. The yurts, btw, book up very far in advance, as does the lighthouse. Yurts are very clean, spacious, heated, but the bathrooms/showers are a short walk away. : )

I grew up in Buffalo, and we used to be able to cross the border with ease so you could even go to lunch and make it back. They basically asked your citizenship, where you're going, and how long you planed to stay and then waved us on. HA! Those days are gone.