Not to knock on the fine folks of Hagerstown, but we should probably get something straight right up front. Hagerstown is no Stars Hollow.
Still, even if it's not my mythical Shangri-La, Hagerstown has some good things going for it. Hands down, best reason to visit Hagerstown is for the antique malls.
Clustered right down historic Route 40 are three solid places. Antique Crossroads is my favorite. While there are certainly some overpriced booths inside this massive building, they are definitely in the minority. You're almost guaranteed to find some great pyrex, mid-century tins and cake carriers, blue ball jars for $2/piece, and so much more. You just have to know which booths to visit. On a recent visit, I walked away from an amazing unicycle and the above dresser.
If you make it through Antique Crossroads and still have energy left, you can head to either Beaver Creek Antiques and A & J Antiques to continue shopping. If you head into downtown Hagerstown, you can get your craft on at the Potomac Bead Company or find a show to watch at The Maryland Theater (though I can't say I saw anything that piqued my interest).
One of my better finds on a recent trip was Hempen Hill BBQ. The venue is fun, waitstaff friendly and the food was fantastic!
They give you enough food for leftovers. And, yes, please forgive the lighting.
Even better is the fact that they have a great selection of vegan and vegetarian fare. As someone who inadvertently begins to crave barbecue when hanging out with vegan friends, this place is downright miraculous. Do yourself a favor and get the smoked mac and cheese.
After you've had a good meal, go for a stroll through some of the Civil War battlefields near Antietam or rent a canoe and paddle down the river.