What if an historic place existed, that was only connected by trails? And then people came along later, and built a town around it, without intruding? How would you get from historic spot to spot? This is exactly the situation that created the Battle Road Trails in Concord, MA. It’s like a marriage of Revolutionary War history, Williamsburg-style reenactment, and a fun trail system of sandy dirt roads. With excellent parking.
For those of a literary bent, let me simply say: Thoreau, Emerson, Alcott, Walden. All within easy riding distance of these road/trails (and any local can and will tell you where). Once you’ve found the main parking lot and HQ, there’s really no getting lost. You might take longer to get back to your car than you expect, but it’s all wide, smooth, and orderly. Not hardcore, but a great place to experience.
The trails are free, but the sites and their gift shops often cost a bit. Not to mention a great bike shop in town.