The town dates back to the late eighteenth century, when, according to local legend, it was founded by two brothers of Daniel Boone. Unsurprisingly, given its proximity to Antietam, it saw major fighting during the Civil War, and housed numerous soldiers following Antietam. In recent history, Boonsboro is primarily an agricultural center, but it's also just a nice historic town for a leisurely lunch or dinner, and perhaps a stop at one of the museums, while exploring the area.
Boonsboro is at the intersection of US-40 and MD-34, so take the MD-34 exit off I-270 to the southeast of Hagerstown and northwest of Frederick. Sharpsburg and Antietam National Battlefield are just southwest of the town on MD-34.
Crystal Grottoes Caverns, 19821 Shepherdstown Pike, ☎ +1 240 217-7623, . Apr-Oct: 10AM-5PM daily, Nov-March: Sa-Su 11AM-4PM. A relatively small, but nonetheless really spectacular, with reputedly more formations per square foot than any other cave in the world. Open to the public as a public show cave under the same family ownership for 80 years, after being spared (for its great beauty) destruction at the hands of the quarry.Adults $15, children $10. Cash only. edit
Washington Monument (Washington Monument State Park), 6620 Zittlestown Rd, Middletown (Go east of Boonsboro for four miles on MD-40 Alternate to the top of South Mountain. Turn left on Washington Monument Rd), ☎ +1 301 791-4767, . Sunrise-sunset daily. On 24 July 1827, the patriotic citizens beat both Baltimore and latecomer Washington, D.C. to the punch in erecting the nation's first Washington Monument. The monument is not in the town itself, but rather just outside on top of South Mountain. There is a museum on-site, open May-Sep daily and weekends only in April and October (closed winter).$2-3/vehicle. edit
Antietam Creek Canoe, 19005 Lappans Rd, ☎ +1 301 447-0444, . Canoes, kayaks, and tubing on Antietam Creek from Devil's Backbone through Antietam Battlefield to Burnside Bridge and to the Potomac. So, it's not just a pretty ride—you'll get to see a good piece of U.S. history along the way, with optional guides.$35-70/person. edit
Old South Mountain Inn, 6132 Old National Pike (US-40), ☎ +1 301 371-5400, . A tavern on the National Road southeast of Boonsboro since 1730, this is both a historic and a fancy place for a French/American dinner. Reservations recommended.$28-48. edit
Palettie, 1 S Main St, ☎ +1 301 432-0500, . The nicest restaurant in Boonsboro proper, this place serves really good Italian food, although they'll make you pay for it. Reservations are a must.$25-40. edit
Inn Boonsboro, 1 N Main St, ☎ +1 301 432-1188, . The first stone building in Boonsboro opened as a hotel in 1790 and remained the town's principal lodging until the twentieth century, when it slid into disrepair. The current owner (Nora Roberts, a New York Times Bestselling author) decided to resurrect the property as a B&B. After a three million dollar renovation punctuated but not deterred by a devastating fire, the building is once more the principal hotel for the town, right on the main square. The eight rooms are named after various literary lovers, and, as you might guess, are quite charming.$220-300. edit
Stoney Creek Farm, 19223 Manor Church Rd, ☎ +1 301 432-6272, . An absolutely beautiful farm out in the countryside, dating back to the eighteenth century, and today a nice Bed & Breakfast.$200-250. edit
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