Not long back from an incredible Christmas/New Year driving from Dallas to Memphis, Nashville, NOL back to Dallas and points in between. It was an amazing trip and I fully intend to do a TR BUT we find ourselves returning to the US this August (late August into September). We have a function to attend in NYC and will spend 5 nights there. This will be our 4th trip so this will be about spending time with family and friends for the 5 days and eating and drinking 'like locals'. We will then have 3 and a bit weeks to go for 'a drive'. We have previously driven from Boston and up but will do the bit between NYC and Boston that we only saw on the train and some places we missed / loved previously. We would love to go as far as PEI then down to Quebec, Montreal and then Chicago for our flight home. We have been to Niagara Falls, so don't really 'need' to revisit but certainly may. As we arrive into NYC and out of Chicago we are mindful and accepting of the one way drop off fee re the rental car, but have decided that the cost is worth it to not go 'backwards'.

I'd love to hear your thoughts on routes, stops, inns, B&B's etc. We love scenic drives/ walks, local food and wine. Thanks as always

My thought would be to take one of many Northeast Regional trains out of New York Penn station to Providence Rhode Island and rent a car to see what you missed between New York and Boston. Return the rental car where you rented it and return on the train to NYP and take the Adirondack train to Montreal and rent a car there for the eastern Canada part of the trip. Return the car in Montreal and take a ViaRail train to Quebec. From Quebec take another train to Toronto. If you want to see Niagara Falls again, you can take a motor coach or a train to the falls.
Fly or take the Amtrak Lake Shore Limited from Buffalo to Chicago. The LSL leaves Buffalo about midnight (sometimes late) every night and is in Chicago in the morning.
Even though it may be legal for you, I have problems with taking a rental car into Canada and returning it to another US location.
Currently, ViaRail is having a dispute with their main infrastructure carrier (CN) and they have shut down operations on nearly all of their trains. I'm hoping that they resolve this before the summer travel season.

<<Currently, ViaRail is having a dispute with their main infrastructure carrier (CN) and they have shut down operations on nearly all of their trains. I'm hoping that they resolve this before the summer travel season.>>

What the heck are you smoking?
https://nationalpost.com/opinion/chr...minal-gridlock

https://www.ctvnews.ca/canada/via-tr...ling-1.4811926

To the OP,
DO NOT take the Adirondack. It is a piece of North American garbage.
Here is a review, which matches my brother's experience to a tee.

https://thepointsguy.com/reviews/amt...k-to-montreal/

He took that piece of trash on advice of a friend, and had sworn off train travel in North America.
From Boston, head up the coast of Maine into New Brunswick and loop through PEI toward Quebec City.
From Quebec City head toward Sherbrooke and the Eastern Townships.

As much as I love PEI I think you are trying to do too much and should skip and do it another time. You can then visit New Brunswick, Nova Scotia and PEI.

Here is a link to our favorite places to visit in PEI.

Halifax and PEI

July and August are the best time to visit PEI you will need at least 5-7 days to get the feel of the island.

Thanks for you speedy replies. I'll look into all suggestions, including rethinking PEI, we may even not decided until we're on the road. We will only book accommodation a few days out from each destination, except NYC and Chicago.

Well... were it ME...
If I were coming from OZ (??) and getting to PEI... I couldn't fathom not going to Nova Scotia on the same trip.

As NS isn't on the way to anywhere, it is someplace you should see when you're nearby.

BUT, the part about Boston kinda narrows your choice for sensible paths.

So, roughly, I would go to these spots in order, perHAPS skipping Toronto and Niagara Falls (where you've already been) in favor of a northern path to Chicago via Sault Ste. Marie

Boston
Saint John, New Brunswick
Cheticamp, Nova Scotia
Halifax, NS
Charlottetown, PEI
Miramichi, New Brunswick
Quebec City
Montreal
Ottawa
(Toronto, OR NOT)
(Sault Ste. Marie?)
Chicago


Of course there are more detailed specifics to cover, but this is a rough outline for starters, to see if you can envison yourselves on such a trek.