If you're a history buff, there are several nearby Civil War battlefields. Megan is partial to this one since it's close to her parent's house.
This is our favorite winery, we're becoming regulars at this point. It's in Funkstown, where Megan grew up, but more than that, they have a wine for all tastes.
If you've never had mead, you're in for a treat. This place is not far from the venue at all, the drinks are good, and the views are nice.
Only open Thursday-Saturday, the Amish Market (as we call it) is awesome! Authentic Amish produce, wood crafts, baked goods, food, candy, you name it, all in one place. Check it out if you have a chance.
The very first monument for President Washington is nearby in Boonsboro, MD. It's a beautiful, scenic drive to the parking lot and short walk up the path to get to the "Milk Jug" as it's often referred to by locals. Once there, you can go inside and look out over the valley towards Hagerstown & Frederick. In October, it should be gorgeous!