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My gf and I are taking a roadtrip in June from Madison to DC. We have 10 days to get there and back and we wanna take our time and see all there is to see on the way there and back. Neither of us have ever been to any of the states we will pass along the way so we're looking for ideas on things to see and where to eat etc. We are open to anything, like the worlds largest frying pan and things like that. Also any suggestions on mom and pop style restaurants would be appreciated!!!
Welcome aboard the RoadTrip America Forums!
Unfortunately, there are literally hundreds of thousands of restaurants and only a handful of regular contributors here. It just is not possible to give meaningful recommendations based on personal experience in a field that large and constantly changing. My best advice is the usual: Go into small towns (away from the Interstate exit ramps) and ask or look for something that appeals to you. Experiment!
Fortunately, you have plenty of time to make the most of your round trip. If there's one direction that you need to do in a relative hurry, then you should use I-94/I-80/I-76/I-70 for that leg. There will be tolls but they are not that bad considering other expenses of the trip. Highlights of this route are Indiana Dunes National Seashore, Cuyahoga National Park outside of Cleveland, perhaps Ohio Amish country as a detour. A longer, more relaxed route would basically follow I-39/I-74/I-70 with major attractions at Indianapolis Motor Speedway, The U.S. Air Force Museum in Dayton, OH, the old National Road (basically US-40) through southwestern Pennsylvania and western Maryland. Outside of Washington on either route are Fort Frederick, the Chesapeake and Ohio Canal, and the Great Falls of the Potomac.
AZBuck