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I say get into your car and just drive the back roads... no major highways. Choose a direction and go, without even looking at a map. ( but I also suggest that you take a cell phone, a map and a GPS for safety)
Just make sure you read the road signs that you aren't entering dead end roads or that you'll be getting stuck or lost on non-maintained roads.
You'll find small towns that are gems and the scenery will most likely beat anything you'd see on a freeway.
I second this. Would love to get lost around the NH area.
The John Jefferies House is probably your best bet for relatively reasonable Boston lodging. Location is very convenient, near the Charles/MGH Red Line stop. You won’t want or need a car.
Have seen several positive posts about the place on the Fodor’s Travel forum. It also looks like the place gets good reviews on sites like Yelp and TripAdvisor. The price looks comparable to 463 Beacon and the reviews are notably better.
Have never stayed at either place, so can’t speak from experience.
Plenty to do in Boston and nearby Cambridge, of course.
Chincoteague is a little far maybe seven hours. But the weather may be better farther south that time of year. You could watch the wild ponies. The motel rates might be good this time of year.
Depending on your interests, and what you may or may not have experienced, and how much road trip meandering you enjoy, you would need to check rates for all these areas but they should all be off season rates except maybe thanksgiving - these would be my suggestions in no specific order:
Coastal Maine pick a smaller port town for relaxation
Hudson River Valley - Saratoga Springs, Mohawk River Valley or all the way up to lake Champlain and crisscross over and back down Connecticut river valley.
Upper Delaware Valley (arts related things)
Susquehanna River Valley -
Western upstate New York - stop in the canal towns all along the old Erie canal (places like Seneca Falls, Frank Capra's inspiration for Bedford Falls in Its A Wonderful Life) to Letchworth State Park in Genesee River valley and stay in bed and breakfast near upper falls (Portageville - Castille, NY) then drive back leisurely through New York's southern tier Route 17 and stop at Corning, Watkins Glen, Ithaca (college town) Nice B & B in Ithaca (Belhurst Castle).
Lots of options it really is up to your interests on what you find nice way to create memories.
Philly! It's about 4 hours from Hartford, and the city is now regularly being mentioned as a top tourism destination by national travel magazines and websites. Lots of history, one of the country's top foodie destinations, easy to get around if you want to leave your car in the hotel parking.
Rent a cabin with a warm and cozy wood stove, somewhere in the woods, maybe on a quiet lake or pond. Don't go too rustic unless you're used to it. You can find something with all the comforts of home, but with zero neighbors. There's nothing better than this.
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