For a challenging hike that some of our forebears did, check out the national park at Gettysburg. The hilly terrain in the foothills of the Alleghenies makes for some tough exercise. Remember from your history books? Places like Little Round Top, Devil's Den, Pickett's Charge, were all sticking points for battle hardened men.
However, you don't have to do it on July 4th weekend in itchy wool uniforms and brogues that didn't differentiate left from right shoes! And you won't have sharpshooters trying to take you out!
Just make sure you are dressed for climbing rocky terrain and in inclement weather, mud.
What a wonderful idea to spend an afternoon with the family.
I am sure throughout the USA there are hiking history lessons.
Being in California, I can think of the Gold Rush era, the first transcontinental railroad, the Donner Party and the Pony Express trail.