Local Attractions
Catoctin Mountain Park
Immediately to the east of Caboose Farm is Catoctin Mountain Park and one of our favorite hiking trails, the 28-mile Catoctin Trail. Check out the small but informative visitor center, where you can learn about the Catoctin Furnace and see a host of taxidermied local wildlife. Camp David, the famous Presidential retreat, is also situated inside the park, less than two miles from our wedding venue. (It’s not labeled Camp David, but you’ll know it when you see it.) Hikers in the park can periodically spot secret service agents trying to look inconspicuous in the woods.
Cunningham Falls State Park
Another of our favorite hiking and camping spots, adjacent to Catoctin and just a short drive from Caboose Farm is Cunningham Falls. You can see live snapping turtles and an aviary filled with owls and - at least last time we went - a rescued bald eagle, at the Manor Area visitors center. The William Houck Area Campground is a great option for folks with kids, as there is swimming, canoeing, and paddleboating in the lake adjacent to the campground. The eponymous Cunningham Falls are also worth checking out. There’s handicap parking and an easy wooden boardwalk up to the falls; folks without a handicap decal can access the falls via a short (roughly 1.4-mile) hike from the Catoctin Mountain Park visitors center.
Civil War history
There’s lots of Civil War history in the vicinity of Caboose Farm. Gettysburg, PA, is about 35 minutes northeast of the farm, and Antietam National Battlefield is about 30 minutes in the other direction. A lesser-known but interesting Civil War site is the National War Correspondents’ Memorial at Gathland State Park, just east of Antietam. The monument itself - an arched stone structure reminiscent of an aqueduct - is dedicated to journalists killed in battle and is a sight to see. The visitors center is also interesting and informative (the enthusiastic volunteers can talk your ear off). The Appalachian Trail passes right by it, so we’ve been there several times on hikes.
The Original Washington Monument
About a half-hour southeast of the farm, in Boonsboro, MD, you’ll find the original Washington Monument. Built by the citizens of Boonsboro in 1827, it was the first monument to George Washington to be completed - nearly sixty years before the more famous Washington Monument in D.C. was built. The monument looks a little like a milk bottle, and there’s a spiral staircase inside by which you can climb to the top for a great view of the valley west of the South Mountain ridge. As the Appalachian Trail passes right by it, the Washington Monument was our midway point on our 42-mile Maryland Challenge last year, when we hiked the entire Maryland section of the AT in one day.
Hiking the AT / Annapolis Rock
The famed Appalachian Trail passes through Maryland just west of our venue. For a really nice day hike, we recommend the Annapolis Rock section, which we did for Chrissy’s birthday this year. Park at the AT Trailhead lot on US-40 and hike north. It’s a really peaceful, relatively flat 2.5-mile trail to the .2-mile connector trail that takes you out to the Annapolis Rock Cliff, which has a great view of Greenbrier Lake and the surrounding valley. Head back to the parking lot for a 5.5-mile roundtrip hike, or if you have more time, continue north to see the view from Black Rock Cliff before heading back to your car (a roughly 8-mile total hike).
Harpers Ferry
If you have a little more time, we highly recommend you take the 45-minute drive down to Harpers Ferry, WV. Harpers Ferry, as you may recall from eighth grade American history, is the site of abolitionist John Brown’s 1859 raid on the federal arsenal in a failed attempt to incite an armed slave revolt. Harpers Ferry has it all: historical sites, quaint cobblestone streets, touristy fudge and ice cream shops, and - surprise - hiking! For an unbeatable view of the town and the confluence of the Potomac and Shenandoah Rivers, hike up the steep hill of the Maryland Heights trail to the cliff overlook. 
For an easier walk from town, ascend the natural stone steps (they’re really cool) up to Jefferson Rock. Thomas Jefferson, in awe of the view from that spot, famously wrote that "this scene is worth a voyage across the Atlantic."
The Appalachian Trail Conservancy HQ is also in Harpers Ferry. Every through-hiker on the AT passes through it, so they’ve got pretty cool pictures and records of all of the hikers, in addition to some excellent AT souvenirs. (We even saw a hiking wedding cake topper there!)
Hagerstown Outlets
There’s outlet shopping on the other side of Hagerstown off I-70, if that’s your thing.