Maryland's Under-The-Radar Town Is An Idyllic Gem With Pristine Natural Beauty And Historic Walking Tours

Maryland's stunning and produce-rich waterfront often grabs the headlines when it comes to travel bucket lists in the Old Line State. Mouth-watering crab feasts are commonplace in Crisfield, the "Crab Capital of the World," sitting right on the scenic Chesapeake Bay, and city design and bay-side architecture go hand in hand in Baltimore, home to one of the best places in the country to explore urban culture. As a result, the hinterland of this gorgeous, hilly, water-fed state is often overlooked. The town of Oakland is as far from the sea as it gets in Maryland. Hugged tightly between the West Virginia and Pennsylvania borders, this wildly underrated town is a treasure trove of historical beauty, with multiple walking tours and monuments to prove it. It also has access to a plethora of parks in its vicinity, to make the most of the pristine beauty of the Allegheny Mountains with their surrounding lakes and rivers.

Oakland, in fact, has two major parks right on its doorstep: the Swallow Falls State Park and Potomac-Garrett Forest, each devoted to the conservation of this unspoiled stretch of enchanting land full of waterfalls, bubbling creeks, oak woodlands, and lush lichen beds.

Located in Garrett County, the youngest in the state, Oakland nonetheless boasts centuries of history, including a starring role in George Washington's quest to open up the strategic Ohio River Valley. Its position makes it very easy to reach from Pennsylvania's steel city, Pittsburgh, about 130 miles away. Pittsburgh is also an ideal connection if you're planning to travel by air, with its international airport located only 4 miles north of the city.

Oakland may appear unassuming to the casual onlooker, but this tiny border town knows it's sitting on a goldmine when it comes to storied architecture and historic buildings. To best guide your travels back in time as you amble across Oakland, the town's historic society has created five walking tours covering different buildings and areas with important stories to tell. The tours are self-led, giving you the freedom to explore whenever and in whatever order you wish, and they come in a printable PDF format or handy Google Maps guide with spots marked and ready to go.

Though every tour has a central theme (such as transportation, commerce, or community), they all touch on key highlights of the town. For example, the Garrett County Museum of Transportation is a hotspot for train memorabilia aficionados, while the 1950s City Hall is an artistic highlight in and of itself, thanks to its Roy Lichtenstein mural commemorating local heroes painted on the side of the building.

A key transport hub in the 1850s, Oakland was once a popular tourist hotspot. Though the lights of mainstream tourism may have dimmed on the town over the decades, Oakland has held on to its thriving arts and entertainment. Once you've polished the walking boots and embarked on one of the five tours, it's time to sit back and relax, and enjoy an exhibition of local, contemporary artists at The Gallery Shop. Make sure to check the town's calendar for regular events and pop-ups, such as the Little Yough Festival in summer or the Autumn Glory Festival in the second week of October, celebrating fall produce and foliage with a marching band and candle-lit gazebo.

Around 500 miles away, America's most visited national park attracts over 13 million visitors yearly. You'll find an infinitesimal fraction of those crowds in the parks around Oakland, and you'll also find that the untouched nature matches the enchantment of the Great Smoky Mountains. Whichever direction you face, you have access to a state park: the Wolf Den Run State Park to the east, Swallow Falls to the north, and Herrington Manor to the west. With such an amazing playground, it's easy to see why active sports like hiking, fishing, and cross-country skiing are so popular.

Straddling the Youghiogheny River, Swallow Falls is home to some of the most captivating mountain views in Maryland. Keep your eyes peeled for flying wonders during migration season, including the Appalachian tiger swallowtail, a rare native butterfly species. Embark on the 5.5-mile-long trail that connects Swallow Falls to Herrington Manor, taking you through the Garrett State Forest, and stop to wonder at the 53-foot-tall Muddy Creek Falls, one of four waterfalls in this park. And make sure to explore the Youghiogheny Grove Natural Area for a taste of the truly pristine, as this area has never been logged and still exists in its unaltered state. Here you can still see the hemlock groves and dark green pine forests, some older than 300 years.

From Swallow Falls, you can easily reach another gem close by, only 10 miles from Oakland. Deep Creek Lake is Maryland's largest freshwater lake and a hotspot for water activities such as boating, fishing, kayaking, and canoeing. Around the lake, you'll also find plenty of spots to unwind after an active day — including dozens of restaurants, such as bakeries suitable for a quick bite to fine dining.