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Road trip from Oakville to Vermont, Maine, Boston - too much in 7 days?

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I am new to Fodors forums and hoping you can help me get started with planning a road trip for my hubby and I in mid October for a week, after our Canadian Thanksgiving!

We love walking (not fond of tourist traps) and enjoying good food (mmm lobster or any type of seafood). We like touring wineries and my husband enjoys sampling local wine/beer. We also enjoy shopping in small towns (trying to stay away from malls) and relaxing by the water. If there's time to get in a golf game to enjoy the fall colours, we might be open to that too.

Other than that, this is our first long road trip and we wanted to enjoy a scenic drive together and be spontaneous.

Any advice on whether Oakville to Vermont, Maine and Boston is too ambitious to accomplish in 7 days?

I heard Portland is good for foodies (we love farm to table restos), not sure if too far to travel to Bar Harbour. Any ideas/suggested routes/day 1 to 7 rough itinerary for a leisurely trip?

Also any suggestions on contemporary hotels or cute bed and breakfasts would be helpful. Am guessing we need to book soon altho looking for flexibility in booking in case our driving plans change.

Finally, we are debating on whether to go through Montreal ... or an alternate drive crossing the border. Decisions, decisions, decisions ...

Thanks so much in advance to all who are open to sharing experiences and/or advice!!

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