Some people look for beaches or restaurants or the best hikes when they travel. I look for bookstores. I know it sounds crazy and I get razzed for it - even my wife who knows me well can't believe it when I ask her to look for bookstores on her iPhone. We have done a lot of traveling this year - to New York state several times, and to Portland, OR and to Alaska. There have been some trips in our home state of Florida, as well. Some times we go out of our way to get to a bookstore that is not on the route Google suggests. Asheville, NC is not really on the way to Buffalo, NY but it has a great bookstore. I had to schedule a side trip and an extra day to the Biltmore Estate so my wife would agree to veering off our straight path north. Saratoga Springs, NY has a gem of a bookstore right on Broadway, the main road through town. Bonus: it's close to a cool coffee shop. And of course, I want to mention that one of our sons and his wife and two children live about twenty minutes away. This bookstore is large, with comfortable seating for browsing and here is what I like most: they have selected used or discounted books scattered throughout the store like hidden treasure. Jacksonville, FL where we live now has two Chamblins locations - a local, used bookstore with shelves of books for browsing and you have to browse because it is hard to find anything you are looking for. Unlike Powells in Portland, a whole city block of new and used books very well organized. I could spend a whole day in there but I am usually with some one else who can't.
Anchorage has Tidal Wave books and Homer has a couple of good bookstores and artist galleries, too. Kodiak used to have a good bookstore: Monks Rock is still a good place to browse books especially if you are interested in the Orthodox Christian tradition and drink coffee. Kodiak has a great library if you are weathered in for an extra day or two.
I could make a trip out of visiting bookstores and have. Flannery O'Connor's homestead is only a five hour drive north of us and the day I stopped by it was closed but I found a bookstore in town. Marjorie Kinnan Rawlings lived and wrote about an hour south of us and I have been there and wandered the grounds. I saw the "house" Zora Neale Hurston stayed in when she came for a visit. Even though it was the servant's quarters it still caused quite a stir. Hemingway lived and wrote in the Florida Keys and you can visit his hangouts there.
I have not made it to Parnassus, Ann Patchett's bookstore in Nashville or Oxford, MS where many people visit for football games but I would be looking for Faulkner's home and the local bookstores which I hear are well worth a visit.
College towns are usually good places to find bookstores. Newberg, OR which is home to George Fox University has a couple. Chapters bookstore is the place to go for coffee and books. Conveniently, our son, daughter in law, and newest grandson live near by. Many college towns I know from our travels do not have a good bookstore. Students are directed to Amazon for their purchases, or in some cases, the local Barnes and Noble,which are becoming fewer as Amazon grows larger. College bookstores mostly exist to sell college merchandise like the big one in downtown Gainesville, FL home to the Gators. There is a nice Christian study center with good coffee a street or two over, however.