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Our Quaint and Historic Towns

Williamsport in Washington County, MD
C&O Canal at Cushwa Basin Williamsport, MD
Inn Boonsboro
Saint Mark's Episcopal Church Lappans Boonsboro, MD

Spend some time exploring Washington County’s many quaint towns. A beautiful and leisurely drive to any of our towns along the Maryland National Road, a Maryland Scenic Byway, or along our Civil War Trail will offer lots of surprises! You never know what hidden gems you’ll uncover in our county’s towns!

Home to best-selling author, Nora Roberts

The town of Boonsboro was founded by brothers George and William Boone (relatives of the more famous Daniel Boone) and was situated along the main road leading from Hagerstown to Frederick. It was laid out in 1792 and incorporated in 1831. About 500 citizens from the town and nearby farms built the Washington Monument, our nation’s earliest monument completed and dedicated in honor of the country’s first president, on July 4, 1827. Today, the town is Washington County’s second-largest municipality. Historic markers explain the National Road, Civil War battles, and more, while quaint shops line Main Street. Nora Roberts' book store, Turn the Page is a favorite stop of the bestselling author's fans, and visitors can stay in her bed and breakfast, Inn BoonsBoro on the Square.

Clear Spring: Sparkling Water and Natural Beauty!
Clear Spring, founded by Martin Myers in 1821, is located 12 miles west of Hagerstown. The historic National Pike—which once linked the port of Baltimore to the western frontier of Ohio—runs through the center of town. The Civil War brought troops and skirmishes, including a large cavalry battle during the retreat from Gettysburg 150 years ago this July. Area attractions include Knob Hall Winery, Whitetail Mountain Resort; the C&O Canal; Fort Frederick State Park; and Camp Harding County Park, named after President Warren G. Harding, who, along with notables such as Harvey Firestone, Thomas Edison, and Henry Ford, camped there in the 1920s.

Funkstown: Antiques, Quaint Shops, & Civil War History!
Founded in 1767 and situated east of Hagerstown, Funkstown was named Jerusalem until its incorporation in 1840. In 1823, the Old National Pike was built through Funkstown, making it a popular stop along the road. (A Civil War battle happened here, too, and reenactments are held every July.) Funkstown continued to grow in the 20th century. However, railroads made the once-bustling community a quiet residential town. Antique stores now line Baltimore Street (Alt. U.S. 40), along with quaint shops and a few eateries. Today, Funkstown—which hosts the popular Olde Tyme Christmas each year—continues to reflect the charm that first attracted early German settlers to the area. 

HagerstownThe Hub City.
After arriving in the area, German immigrant Jonathan Hager built the first house here in 1739. He began laying out the town in 1762. The Hager House still stands as a carefully preserved museum, giving visitors a window to the 18th century.

The National Road brought growth to Hagerstown, now Washington County’s largest city and the railroads intersecting here gave it its nickname, “Hub City.” The largest Civil War cavalry battle fought in an urban setting happened here in July 1863. There are many award-winning historic Civil War markers throughout the area. Of special note are Downtown Hagerstown and the Arts and Entertainment District, where you’ll find wonderful shops, restaurants, and such cultural attractions as the Maryland Theatre, the Washington County Arts Council Gallery, the Maryland Symphony Orchestra, and the Washington County Museum of Fine Arts.

Hagerstown City Park offers 50 acres of beautiful outdoor space. You’ll also enjoy golfing at Hagerstown Greens at Hamilton Run, swimming at Claude M. Potterfield Pool, and visiting Fairgrounds Park. Shopping opportunities abound at the Valley Mall and Hagerstown Premium Outlets. And stop by Hagerstown City Farmers Market for homegrown produce from area farmers, as well as crafts and baked goods.

Hancock: Recreation & Commerce Hub!
Hancock is the westernmost town in Washington County, situated on the Potomac River at the narrowest point in Maryland. In 1818, the National Pike, Hancock’s Main Street, was officially opened.

During the Civil War, Hancock became an important town in the struggle for control of the C&O Canal and the Potomac. Confederates shelled the town from across the Potomac River, and later held it for ransom. 

The C&O Canal National Historic Park visitor’s center at the Bowles House is a gem of curated living during the Canl's heyday. Other attractions include antique and specialty shops, the Blue Goose Fruit Market and Bakery, and several restaurants, and outdoors enthusiasts can explore the C&O Canal Towpath and Western Maryland Rail Trail. The Tuscarora Trail of West Virginia, passes into Maryland where it joins and uses the C&O Canal towpath to Hancock, MD.  Here it crosses the Potomac River and connects to the Big Blue Trail. 

boat launch onto the Potomac is located in Hancock, along the C&O Canal at Little Tonoloway Recreation Area in Hancock. The C&O Canal Bicycle Shop offers shuttles. 
For additional info, visit the town's website: Hancock, MD

Keedysville & Rohrersville: Railroads & Rural Charm!
Located eight miles south of Hagerstown, Keedysville was once a vital link on the B&O Railroad. Today, it boasts a unique combination of farmland and Victorian architecture.  Little Antietam Creek is an attractive focal point. Taylor Park provides visitors with recreational facilities. Bonnie's at the Red Byrd offers delicious home-style meals. In the neighboring hamlet of Rohrersville, sip some local varietals at the scenic and award-winning winery, Big Cork Vineyards.

While real Civil War battles are remembered here, several motion picture and TV documentaries about the war have been filmed in and around Keedysville, too. Crystal Grottoes Caverns lies just west of town.

SharpsburgCivil War Legacy. 
Sharpsburg is intrinsically tied to the Battle of Antietam. On September 17, 1862, this peaceful town was the place where two massive armies clashed, leaving 23,110 dead, wounded, or missing. Every building overflowed with the wounded and dying. After the war, Sharpsburg’s population declined; today, it has fewer than 700 residents, many directly descended from families here during the Civil War. The Antietam National Battlefield and the Antietam National Cemetery are part of Sharpsburg, and nearby museums such as the Pry House Field Hospital Museum attract international symposiums. Visit the Newcomer House Exhibit and Visitor’s Center just past the Antietam Cemetery, try a famous Nutters Ice Cream treat, and eat at Captain Benders Tavern. sharpsburgmd.com

Smithsburg: Apples & Orchards Abound.
Smithsburg was incorporated in 1846. The town played a role in the Civil War, when residents helped care for wounded soldiers after the battles of Gettysburg, Monterey, South Mountain, and Antietam. In addition, there was a cavalry battle here during the Confederate Retreat from Gettysburg, 150 years ago. There is a Civil War Trails marker on the site, just east of MD 77.

Interesting local attractions include the Smithsburg Town Museum and Smithsburg Veterans Park. The annual Steam and Craft Show, Smithsburg Pride Days, and other events attract thousands. Visit nearby Red Heifer Winery, and also the many orchards and fruit stands! townofsmithsburg.org

Williamsport: Epi-Center of the C&O Canal.
Once considered a potential site for the United States’ capital, Williamsport is located at the confluence of Conococheague Creek and the Potomac River. With the opening of the C&O Canal in 1834, it evolved into a thriving waterfront town.

During the Civil War, the swollen waters of the Potomac at Williamsport prevented Gen. Robert E. Lee’s army—retreating from Gettysburg—from crossing into Virginia for several days. The Civil War might have ended in Williamsport, but the Confederates held the town against Union attacks until finally slipping back into Virginia. Today, Williamsport has many fine businesses and recreational opportunities. Be sure to visit the town museum, the newly restored Civil War cannons high atop Doubleday Hill, and the C&O Canal National Historical Park. Williamsport is also the finish line for the annual JFK 50 Mile, the largest, oldest, and most prestigious ultra-marathon in North America. williamsportmd.gov