Quaint Historic Towns

A 19th-Century Marvel

Trace the events leading up to the bloodiest single day in American history on the Antietam Campaign Scenic Byway. This 126-mile route, mirroring General Lee’s march, traverses Montgomery and Frederick counties before reaching South Mountain, where Confederate and Union troops clashed before their fateful meeting at Antietam. Walk the preserved battlefields of South Mountain State Park and Antietam National Battlefield, and explore the surrounding towns. The largely unchanged rural landscape offers breathtaking vistas just as they appeared to our ancestors.

A Journey Through U.S. History antietam campaign byway boonsboro: an appalachian trail town and home of best-selling author, nora roberts clear spring: crossroads of commerce

Explore Washington County’s charming towns. Scenic drives along our three byways—Maryland Historic National Road, Antietam Campaign, and the C&O Canal Byway—promise hidden gems.

Founded in 1792 on the main road from Hagerstown to Frederick, the Maryland National Road, Visit the Washington Monument, along the Appalachian Trail, dedicated in 1827. Explore the newly opened National Road Museum and quaint Main Street shops like Josie’s on Main. Nora Roberts’ fans can visit her shops, Turn the Page and Gifts Inn Boonsboro, as well as stay at her Inn BoonsBoro on the Square. Visit the Boonsboro Trolley Musuem and the newly opened National Road Museum.

Founded in 1821 by Martin Myers, this historic town 12 miles west of Hagerstown was a popular stop on the National Road. Myers’ crock and jug shop grew into a small hotel, attracting pioneers to stay at the “hotel by the spring.” Today, visit the historic Wilson Store and you can grab a bite at Sweetsie’s Eats & Treats! Other nearby attractions include Whitetail Mountain Resort, Hagerstown Speedway and Fort Frederick State Park.

funkstown: quaint shops & civil war history

In 1823, the Old National Pike was built through Funkstown, making it a popular stop along the way, heading west. A Civil War battle happened here, too. Antique stores now line Baltimore Street (Alt. U.S. 40), along with quaint shops and a boutique winery and tasting room, Blue Mountain Wine Crafters.

hagerstown: the hub city hancock: maryland’s official trail town! keedysville & rohrersville: railroads & rural charm! smithsburg: history, intrigue and orchards williamsport: epicenter of the c&o canal

German immigrant Jonathan Hager built the first house here in 1739. The Jonathan Hager House & Museum still stands as a carefully preserved museum, giving visitors a window to the 18th century. The Historic National Road brought growth to Hagerstown, our Capital and largest city. This and the railroads intersecting here gave it its nickname, “Hub City.” Our City Center, in Downtown Hagerstown and the Arts and Entertainment District, where you’ll find restaurants, and such cultural attractions as The Maryland Theatre, home of the renowned Maryland Symphony Orchestra. Stroll the Cultural Trail to our Museum of Fine Arts. A great game of golf can be played at Black Rock Golf Course or at Hagerstown Greens at Hamilton Run.

The westernmost town in Washington County, it is situated on the Potomac River at the narrowest point in Maryland. In 1818, the National Pike, Hancock’s Main Street, was officially opened.

The C&O Canal National Historical Park  runs along the southern border of the town. Hop off the trails to visit antique and specialty shops, such as the Blue Goose Fruit Market and Bakery and Flannel on the Trail, and restaurants such as the pet-friendly Buddy Lou’s Eats Drinks & Antiques. Cyclists can get bike services and shuttled by the C&O Canal Bicycle Shop.

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. Sip some local varietals at the scenic and awardwinning winery, Big Cork Vineyards. Crystal Grottoes Caverns lies just west of town and is Maryland’s only commercial cavern.

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 casualties. The Confederate loss at the Battle prompted President Lincoln to issue the Preliminary Emancipation Proclamation. The Antietam National Battlefield and the Antietam National Cemetery, Pry House Field Hospital Museum and Newcomer House Exhibit and Visitor’s Center are must see sites to grasp the immense effect of the day. Grab a bite at the Battleview Market or Bonnie’s at the Red Byrd with delicious home-style meals. Sip some wine after touring the sites at Antietam Creek Vineyards.

Established 1846, this Gettysburg retreat town thrives with farms and wineries. Enjoy Red Heifer Winery’s cozy winter igloos, perfect for group gatherings with stunning mountain views and local wines. Or, find fresh produce at local orchards. Discover Fort Ritchie: historic Army post, now a developing village with scenic trails.

At the center of the 184 miles of the C&O Canal Towpath, it is often called the “Jewel in the Necklace” of this National Historical Park. The 1934 opening of the C&O Canal transformed this town into a thriving waterfront community, along the Potomac River. Offering an abundance of hiking, biking, kayaking and other water sports, visitors can jump off the Canal for dining, bike repair, and lodging.

Quaint Historic Towns

Explore Washington County’s charming towns. Scenic drives along our three byways—Maryland Historic National Road, Antietam Campaign, and the C&O Canal Byway—promise hidden gems.

Founded in 1792 on the main road from Hagerstown to Frederick, the Maryland National Road, Visit the Washington Monument, along the Appalachian Trail, dedicated in 1827. Explore the newly opened National Road Museum and quaint Main Street shops like Josie’s on Main. Nora Roberts’ fans can visit her shops, Turn the Page and Gifts Inn Boonsboro, as well as stay at her Inn BoonsBoro on the Square. Visit the Boonsboro Trolley Musuem and the newly opened National Road Museum.

Founded in 1821 by Martin Myers, this historic town 12 miles west of Hagerstown was a popular stop on the National Road. Myers’ crock and jug shop grew into a small hotel, attracting pioneers to stay at the “hotel by the spring.” Today, visit the historic Wilson Store and you can grab a bite at Sweetsie’s Eats & Treats! Other nearby attractions include Whitetail Mountain Resort, Hagerstown Speedway and Fort Frederick State Park.

In 1823, the Old National Pike was built through Funkstown, making it a popular stop along the way, heading west. A Civil War battle happened here, too. Antique stores now line Baltimore Street (Alt. U.S. 40), along with quaint shops and a boutique winery and tasting room, Blue Mountain Wine Crafters.

German immigrant Jonathan Hager built the first house here in 1739. The Jonathan Hager House & Museum still stands as a carefully preserved museum, giving visitors a window to the 18th century. The Historic National Road brought growth to Hagerstown, our Capital and largest city. This and the railroads intersecting here gave it its nickname, “Hub City.” Our City Center, in Downtown Hagerstown and the Arts and Entertainment District, where you’ll find restaurants, and such cultural attractions as The Maryland Theatre, home of the renowned Maryland Symphony Orchestra. Stroll the Cultural Trail to our Museum of Fine Arts. A great game of golf can be played at Black Rock Golf Course or at Hagerstown Greens at Hamilton Run.

The westernmost town in Washington County, it is situated on the Potomac River at the narrowest point in Maryland. In 1818, the National Pike, Hancock’s Main Street, was officially opened.

The C&O Canal National Historical Park  runs along the southern border of the town. Hop off the trails to visit antique and specialty shops, such as the Blue Goose Fruit Market and Bakery and Flannel on the Trail, and restaurants such as the pet-friendly Buddy Lou’s Eats Drinks & Antiques. Cyclists can get bike services and shuttled by the C&O Canal Bicycle Shop.

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. Sip some local varietals at the scenic and awardwinning winery, Big Cork Vineyards. Crystal Grottoes Caverns lies just west of town and is Maryland’s only commercial cavern.

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 casualties. The Confederate loss at the Battle prompted President Lincoln to issue the Preliminary Emancipation Proclamation. The Antietam National Battlefield and the Antietam National Cemetery, Pry House Field Hospital Museum and Newcomer House Exhibit and Visitor’s Center are must see sites to grasp the immense effect of the day. Grab a bite at the Battleview Market or Bonnie’s at the Red Byrd with delicious home-style meals. Sip some wine after touring the sites at Antietam Creek Vineyards.

Established 1846, this Gettysburg retreat town thrives with farms and wineries. Enjoy Red Heifer Winery’s cozy winter igloos, perfect for group gatherings with stunning mountain views and local wines. Or, find fresh produce at local orchards. Discover Fort Ritchie: historic Army post, now a developing village with scenic trails.

At the center of the 184 miles of the C&O Canal Towpath, it is often called the “Jewel in the Necklace” of this National Historical Park. The 1934 opening of the C&O Canal transformed this town into a thriving waterfront community, along the Potomac River. Offering an abundance of hiking, biking, kayaking and other water sports, visitors can jump off the Canal for dining, bike repair, and lodging.