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There’s something for everyone in Washington County, Maryland, whether it’s your first trip or you keep returning to your favorite scenic nature trails over and over again. With summer just around the corner, now is the time to start planning your next great road trip. Located about three hours from Philadelphia and Pittsburgh, or 90 minutes from Washington, D.C. and Baltimore, this particular part of the state is full of historic Civil War battlefields and scenic byways showcasing the area’s natural beauty. If you’re up for a memorable drive full of history, hiking trails, charming small towns, historic inns, wineries, breweries, and plenty of Americana, add these three scenic byways to your next Western Maryland road trip itinerary.
The Maryland Historic National Road Scenic Byway
Historic National Road – Credit: Scott Cantner
While the entire Historic National Road reaches across six states from Baltimore, Maryland, to East St. Louis, Illinois, a large portion of Maryland’s stretch of it passes through Washington County, following Maryland Route 144 and US Route 40 Scenic (also called US Route 40 Alternate), which runs parallel to US Route 40 from Frederick to Hagerstown. As you drive on the scenic byway, built between 1811 and 1834 and dotted with historic sites, charming small towns, and stunning natural scenery, it’s not hard to imagine early American settlers and traders traveling along the same route in their horse-drawn carriages.
Popular stops within Washington County include Washington Monument State Park, where you can hike a small section of the legendary Appalachian Trail and view the first stone monument ever created in honor of George Washington, and South Mountain State Park, which is located nearby and part of a popular migratory trail. Visit the National Road Museum in Boonsboro to learn more about US Route 40, the first federally funded highway in the U.S., and snap photos of the town’s charming 19th-century buildings. Nora Roberts fans can also make a pilgrimage to her beloved Turn the Page Bookstore and Café, where she still does the occasional book signing, or stay at the Inn BoonsBoro, a literary-themed bed and breakfast opened by the esteemed bestselling author and her husband in 2009. Head to Big Cork Vineyards for a glass of locally made wine or enjoy a meal at Old South Mountain Inn, known for its dining since 1732.
Antietam Brewey – Credit: Scott Cantner
Spend some time in Hagerstown, often referred to as the “Hub City” due to its location at the crossroads of several major trading routes — by land and water — and eventually, because of its many modern-day railway and highway connections. If you’re craving a little culture on your road trip, visit the Washington County Museum of Fine Arts or catch a show at The Maryland Theatre, where the Maryland Symphony Orchestra is based. Stroll along the Hagerstown Cultural Trail, which connects the theatre district with the fine arts museum in City Park. Just a 10-minute drive from downtown Hagerstown, Antietam Brewery is worth a stop for its creative craft brews, tasting room, behind-the-scenes tours, and outdoor patio, while Blue Mountain Wine Crafters in nearby Funktown offers a dog-friendly stop for lovers of all things vino.
Next, head west to Ford Frederick State Park in Big Pool, home to a unique stone fort that dates back to 1756 and once protected Maryland during the French and Indian War — it’s also home to several hiking trails where you can spot white-tailed deer, birds, turtles, and other wetland wildlife. Nearby, seafood lovers can tuck into crab cakes, crab legs, oyster po’boys, and other surf and turf delights like prime rib and smoked beef brisket sandwiches at Jimmy Joy’s Log Cabin Inn — just make sure you save room for homemade coconut cake or Queen City Creamery frozen custard for dessert.
Other places worth checking out along the scenic byway include the Town Hill Overlook in Little Orleans and, just beyond Washington County’s boundaries, Rocky Gap State Park in Flintstone, the Great Allegheny Passage (which starts in Cumberland, Maryland and ends in Pittsburgh, Pennsylvania) and charming small towns like Cumberland, Frostburg, and Grantsville, gateway to Casselman River Bridge State Park.
If you’re short on time, consider breaking up your Maryland Historic National Road Scenic Byway road trip by interest or section, as its Eastern and Western portions extend well beyond Washington County and cover all sorts of historic sites, quaint country towns, and other intriguing attractions.
The Chesapeake & Ohio (C&O) Canal Scenic Byway
Lockhouse on C&O Canal near Cushwa Basin – Credit: Betsy DeVore
Travel along the C&O Canal Scenic Byway from Cumberland to Hagerstown and points beyond via several Maryland routes (65, 63, 68, 56, 51, and 144, as well as I-70 and US 40), following the Chesapeake & Ohio (C&O) Canal National Historic Park, an extensive 184.5-mile waterway connecting Washington, D.C. with Cumberland, Maryland. The C&O Canal Towpath runs alongside it, acting as a major destination for runners, cyclists, and anyone in need of a long walk by the Potomac River. If you prefer a paved path, the adjacent Western Maryland Rail Trail, which runs 28 miles between Big Pool and Little Orleans, makes a great option for those longing to stretch their legs.
While Williamsport is a major center of activity along the C&O Canal Scenic Byway, with opportunities to check out the inner workings of the lock during a 1900s-era boat ride or by spending the night in a traditional lockhouse, there are a few other spots worth visiting along the canal as well.
In Hancock, grab a bite or pick up some locally made souvenirs at The Blue Goose Market, home to a popular bakery, then stop by the visitor center to learn more about the town’s history beside the busy canal system.
Get some fresh air by taking a hike in the Sideling Hill Wildlife Management Area, home to some of the area’s oldest geology, as well as songbirds, white-tailed deer, black bears, grouse, and wild turkeys. If time allows, hike up to Paw Paw Tunnel, which takes you up from the campground through a pitch-black tunnel (don’t forget to bring a flashlight!) so you can view waterfalls on the other side. If you’ve managed to work up an appetite after all that, head to Buddy Lou’s Antiques and Eats for delicious Southern-style treats like fried green tomatoes, mac and cheese, and crabcake sandwiches.
Another popular canal town, Sharpsburg, is known for its proximity to Antietam National Battlefield and for being part of its own scenic byway.
The Antietam Campaign Scenic Byway
Antietam Old Simon Civil War Soldier – Credit Scott Cantner
Think of the Antietam Campaign Scenic Byway as the ultimate open-air Civil War museum, taking visitors from White’s Ferry along several Maryland Routes — 107 and 109 to Hyattstown, 355 to Frederick, US Route 40 Alternate to Middletown, 17 to Gathland State Park, 67 to Knoxville, 340 to Harpers Ferry National Historical Park, and US Route 40 Alternate — through Middletown and Boonsboro to Antietam National Battlefield in Sharpsburg.
Popular stops include historic White’s Ferry, C&O Canal National Historical Park (which we just talked about), and Little Bennett Regional Park in Hyattstown. Next, you’ll hit Monocacy National Battlefield in Frederick, where the fighting raged on and essentially saved Washington, D.C. from a Confederate invasion, Gathland State Park, home to a large stone monument created to honor Civil War correspondents, and South Mountain State Battlefield, which helped turn the tide of the war in favor of the Union.
Antietam Battlefield – Credit: National Park Service
The scenic byway ends at its most well-known stop, Antietam National Battlefield, where on September 17, 1862, roughly 23,000 soldiers were killed in what is now known as the bloodiest single-day battle in American history — check the website, as there will be special events held over the weekend of September 17, 2022, to mark the 160th anniversary. All year long, you can learn about the battle and those who fought and died there at the visitor center, hear about Civil War medicine at the Pry House Field Hospital Museum, and reflect on the lives that were lost at Antietam National Cemetery. Raise a glass to history and those who came before at Antietam Creek Vineyards, also located in Sharpsburg, offering several locally made vintage white, red, and rosé wines and views of the nearby battlefield.

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