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My best friend and I are driving to Chicago soon and are hopping to camp out instead of staying in motels on the way. We're also trying to fill the trip with as many roadside oddities and adventures as possible without driving too far off course. We'll be going through Mass on 495 and then taking 84 through CT, NY, and Penn where we'll reach i80 which takes us through northern Ohio and Indiana to Chicago. If anyone has any suggestions ext, we'd really appreciate it ^_^
-Liv
Welcome aboard the RoadTrip America Forums!
You don't say how long you have for the drive, but since you note that you don't want to stray too far from your direct Interstate route, I'd assume that you only have a couple of days to get to Chicago. In that case you really don't have a lot of time to go wandering off the highway and will have to cover a solid 550 miles or so each day. And unless you are very familiar with your equipment you'll want to be at your campsite early enough to set up while it's still light out. Looking for camping around the halfway mark leads me to suggest either Black Moshannon or Parker Dam State Parks. For places not too far off your route that would make pretty good conversation starters, try Gobbler's Knob in Punxatawney, PA. If you have more time, there is a lot more to see/do. With just one extra day you can be looking at taking some very scenic alternatives to the Interstates such as US-6 across the northern tier or Pennsylvania, and making stops in venues like the Delaware Water Gap and Cuyahoga Valley National Park.
AZBuck
Just did that route (ME to MN, via Chicago) a couple weeks ago. I picked up a brochure at an IN rest stop that shows attractions right off the highway. (Not in the house I am now or I'd share the name of it, sorry.) Check to see if maybe the IN highway dept has the info online? Or else pick it up as soon as you cross the border. We're planning to stop at a few on our way home.
A silly site/sign we saw on the way was for the Jello Museum outside Batavia NY. My daughter wanted to see that just for kicks, too.