15 Best Things to Do in Oakland, MD

Oakland, MD
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The county seat of Garrett County, Maryland, is the town of Oakland, a small town with oodles of charm.

It sits near the source of the iconic Potomac River, flowing right into the Chesapeake Bay.

During the winter, the town transforms into a skiing hub because of its closeness to Deep Creek Lake’s Wisp Resort.

Tourists from Maryland and other places visit the ski resort for a memorable winter experience.

Speaking of history, the town of Oakland officially became one in 1862.

It’s also a unique tourist destination for rail enthusiasts.

For instance, the town maintains the historic B&O Railroad station, listed in the National Register of Historic Places in 1973 and restored in 2000.

Today, trains still run on the tracks behind the station; however, they only operate during special gatherings or for special organizations.

Oakland teems with historical landmarks and natural attractions that warrant a visit, or at least a close look.

Do you want to know more about Oakland, MD?

Here’s a list of the best things to do in town:

Learn Train History at the B&O Railroad Museum

A red train at B&O Railroad Museum
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In 1828, the Baltimore and Ohio Railroad began constructing its headquarters in Oakland.

Three years later, the railroad finished and became the first commercial railroad in America, originally named the West Pratt Street Depot.

Then, the station changed its name to Mt. Clare Depot and expanded throughout the country.

The station has also seen various milestones.

Front part of a steam train at B&O Railroad Museum
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For instance, in 1830, the first steam engine in America, the Tom Thumb, made its home in Mt. Clare.

In 1844, the station also received the first telecommunications message in the world, a Morse Code telegram.

Today, this iconic railroad is now the B&O Railroad Museum.

You can join tours of the premises or ride the train along the country’s first commercial railroad.

The tours are available for the general public, kids, and private groups of 20 or more.

Interior of the B&O Railroad Museum
Esther Westerveld from Haarlemmermeer, Nederland, CC BY 2.0, via Wikimedia Commons

Spend the Day at Herrington Manor State Park

This 365-acre public recreation area near Oakland gives you the chance to relax and hang out in a calming lakeside environment.

Its main attraction is the 53-acre Herrington Lake, and it also has significant historical value.

For instance, the park gets its name from the real estate investor Abijah Herrington, who built a manor house in the area during the 1800s.

In 1935, the state of Maryland bought the property in the process of developing a state forest, damming Herrington Creek to create the lake.

To make way for the state park, the state demolished the manor house in 1964.

Today, the lake opens up a variety of water activities, like swimming, boating, and fishing.

On the other hand, you can hike or bike along 12 miles of trails and rent cabins for your family.

Revisit Town Origins at the Garrett County Historical Museum

If you’d rather spend an afternoon indoors, you won’t go wrong with a visit to the Garrett County Historical Museum.

You’ll find this museum in the heart of Oakland, housing 200 years of historical artifacts in one place, which you can tour in one afternoon.

This museum has nine rooms.

Each of these rooms covers a specific historical period in Garrett County.

For instance, you’ll learn more information about the B&O Railroad, the Deer Park and Oakland Hotels, and many others.

Likewise, you’ll find out the history of the county’s schools, the coal mining industry, and the Opra house.

Before you leave, you might also want to buy a book on Garrett County from the gift shop.

Spot Birds at Broadford Lake

Oakland’s Broadford Lake offers the usual lakeside attractions such as boating and hiking, but you should also visit for bird-watching.

You literally won’t run out of birds to observe because people have already spotted more than 210 species in the park and lake.

The park might be small, but it has abundant birdlife. For example, songbirds flock to this place every summer and fall.

Likewise, you can see enormous flocks of Canada Geese and various species of ducks floating on the lake.

You might even catch a migrating shorebird resting on the beach area or the wetland across Broadford Road.

For rare species, you’ll want to look out for the Cackling Goose, the Eurasian Wigeon, the Red-throated Loon, the Red-necked Grebe, and many others.

Roll a Strike at The Alley Bowling Center

The only ten-pin bowling alley in the entire Garrett County is in Oakland, aptly named The Alley.

They offer a delightful bowling experience for friends and families, with some lanes geared toward kids.

For example, they can rent bowling shoes for toddlers with size 7 feet, and they have ramps and bumpers for the kids’ lanes.

Teach them the magic of bowling early at The Alley.

Likewise, The Alley hosts regular bowling tournaments as fundraising events.

The center is also available for meetings, parties, family reunions, team-building events, and so much more.

Bring your friends and enjoy warm pizza while you compete for the title of Best Bowler at The Alley.

Explore the Outdoors at the Swallow Falls State Park

Colorful trees surrounding a waterfall at Swallow Falls State Park
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Gorgeous scenery and a wonderful natural environment await you in Swallow Falls State Park, one of Maryland’s most popular parks.

You’ll see the beautiful Youghiogheny River crossing the park, cutting across tough gorges to create exciting rapids.

A woman admiring the falls at Swallow Falls State Park
Richard Bizick / Shutterstock.com

Likewise, you can also see the 53-foot Muddy Creek Falls crashing into a pool of cool water.

You’ll also want to follow the park’s 1 ¼-mile trail to experience the most majestic views in Western Maryland.

The park itself saw famous American figures pass its premises.

A man fly fishing at Swallow Falls State Park
Steve Heap / Shutterstock.com

During the summer of 1921, Harvey Firestone, Thomas Edison, and Henry Ford camped for two weeks at the present location of Swallow Falls State Park.

Follow the footsteps of these titans of the industry by visiting Swallow Falls!

Wooden trail of Swallow Falls State Park
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Become a Cowboy at Circle R Ranch

This family-friendly ranch should also help you fulfill your cowboy dreams.

Likewise, your kids dreaming of getting a pony for Christmas should get the next best thing.

The Circle R Ranch offers free barn tours where you can get up close and personal with their horses before riding them.

Your kids can also ride the ponies there, while the adults can take the horses down the trails.

If you want a trail to yourselves, you can book a tour along the private trails.

After riding the horses, you can enjoy the company of your family by the bonfire while the stars shine in the sky.

During the winter, the ranch offers one-horse open sleigh rides.

Snuggle with your family under the blankets as the sleigh takes across the snowy landscape.

Ride the Wind at the Western Trails Riding Stable

Since 1970, the Western Trails Riding Stable have offered memorable trail rides to curious guests wandering into the Deep Creek Lake area.

Over the years, the stables have added horse shows, camping, horse breeding, and riding lessons.

You can enjoy the feeling of traveling on horseback at the stable while learning about the different breeds living there.

For instance, you can ride Paints, Quarter Horses, Pintos, and huge draft horses.

While riding the trail, you might also spot wildlife like wild turkey or whitetail deer strolling along with the unspoiled mountainside landscapes of Deep Creek Lake.

If you're not feeling the horses, they have also added off-road ATV tours.

The stables are open year-round to everyone of all ages, skills, and experience levels.

Unwind at the Sipside Lounge

If you’d rather stay downtown, you might want to make it a night by visiting the Sipside Lounge in the heart of Oakland.

You’ll find the bar inside a century-old space whose historic fireplace draws your eye the moment you step into the Fireside Patio.

Why not?

After all, it’s the largest stone fireplace in all Maryland, looming over the space since the 1930s.

Bring your friends for a night on the town and enjoy delicious drinks and pleasant live music.

Then, stretch your legs for a bit by heading next door to Flipside Sounds, a vinyl record store that sells all the vintage LPs you haven’t heard before.

Enjoy the Company of Nature at the Potomac-Garrett State Forest

You’ll find the birthplace of Maryland forest conservation right here in Oakland. Just drop by the Potomac-Garrett State Forest, located in southwestern Garrett County.

In 1906, the Garrett Brothers donated a 1,917-acre tract of land to the state, which became the foundation of the eventual State Forest.

Likewise, the property also gave rise to the state's present Public Lands and Forest Service systems.

You can do a lot of things at this state forest, from camping, geocaching, fishing, hunting, trapping, and even archery.

The Potomac-Garrett State Forest’s archery range is also the only 3-D range in all of Maryland’s Public Lands system.

Kids younger than 11 can also shoot arrows here for free.

On the other hand, adults need to pay $7 per round, while kids 12-16 years old need to pay $5.

Go Hunting at the Mt. Nebo Wildlife Management Area

If you want to see some unique landscapes and forests in Oakland, visit the Mt. Nebo Wildlife Management Area.

This 1,854-acre property covers Maryland’s unique geographical features, the two red spruce bogs.

Why are these bogs special?

These bogs are historic since they are a couple of the oldest peat bogs you can find in eastern North America.

Likewise, these old bogs support a variety of endangered rare plants.

This area also supports river otters, occasionally swimming along the beaver pond or waterfowl impoundment.

You can spot turkeys, ruffed grouse, and songbirds around the area, too.

However, Mt. Nebo’s main attraction is hunting for ruffed grouse or woodcock.

Visit during the fall to catch migrating waterfowl stopping by the man-made pond or “impoundment.”

You can also hunt white-tailed deer and even bears.

Just make sure to know the hunting seasons and shooting hours before lugging your rifle along.

Other Things to Do Nearby

Go Skiing at Wisp Resort

People outside Wisp Resort's center
Wirestock Creators / Shutterstock.com

This time, drive 21 minutes away from Oakland to reach the community of McHenry, Maryland.

You’ll find the state’s only ski resort in Maryland that’s open for four seasons, which also offers golf and recreation.

This resort is the Wisp, a family-friendly winter wonderland.

A man in the middle of a ski jump at Wisp Resort
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During your visit, you’ll have 172-acres of ski terrain to experience, which should be more than enough for fans of snow sports.

You can choose from various options, from snowshoeing, riding the mountain coaster, or cross-country skiing.

A person skiing at Wisp Resort
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Even if you don’t like snow sports, you’ll still find something to enjoy at Wisp.

You can join the resort’s Canopy or Segway Tours, try downhill mountain biking, or play disc golf with buddies.

Otherwise, you can even try whitewater rafting or flatwater kayaking.

Sunset reflecting on a body of water at Wisp Resort
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See Artists at Work Inside the Spruce Forest Artisan Village

You might need to go a fair distance from Oakland to reach the Spruce Forest Artisan Village, but the trip should be worth it.

This village is a 37-minute trip away from Oakland, located in Grantsville, Maryland, and it’s a unique spot because it’s a dedicated space for local artists to sell their work.

It’s also a place where the visitors can interact directly with the artists inside their work studios.

You can hear and learn from the six resident artists and the many visiting artists who are more than willing to share their stories, advice, and artistic processes.

This village is so popular that it attracts upwards of 60,000 guests every year.

During your visit, you may also want to visit the historic Stanton’s Mill, constructed in 1797 but operated up to the mid-1990s.

The mill kept functioning thanks to sustained modernization efforts.

Today, the mill has become a famous attraction, working as it did in the 1800s.

Take Photos of the Bloomington Viaduct

A little closer to Oakland, the Bloomington Viaduct stands in Bloomington, Maryland, just 28 minutes away.

This railroad bridge connected Bloomington and Mineral County, West Virginia, spanning the Northern Branch of the Potomac River.

In 1851, the bridge opened to service the main line of the Baltimore and Ohio Railroad.

Many years later, in 1916, the company widened the line to fit two more tracks.

The National Register of Historic Places listed the Bloomington Viaduct in its records in 1976.

What can you do at this bridge?

You can snap photos of this historic structure and pay homage to Maryland's rich history of transportation.

It’s also a nice spot to relax by strolling along the bridge.

Learn to Fly Fish at Maryland Mountains Fly Fishing

If ordinary fishing bores you, then why not try fly fishing?

Learn from the expert Tony Lolli, who runs Maryland Mountains Fly Fishing out of Grantsville.

Drop by his place to learn fly fishing at various spots on the Appalachian Mountains.

You can choose the Savage, Youghiogheny, Casselman, or the North Branch of the Potomac.

Tony’s 50-year fly fishing and 40-year guiding experience will steer you through the basics of fly fishing.

His shop is available nearly throughout the year, thanks to bottom-release dams that release 54-degree water all year.

Likewise, Tony caters especially to beginners, and he guides both individuals and families.

Don’t even worry about equipment because Tony will provide it for you.

Final Thoughts

Oakland might be a small town, but it’s got historical landmarks and natural attractions in spades.

Plus, you can even venture to other nearby communities to enrich your splendid vacation.

If you just want a weekend getaway in a quiet town, book your Oakland trip today.