The Perfect Fall Road Trip in Maryland!

Maryland is steeped in incredible history. One would be foolish not to take that into account when planning any fall road trip through the state. Fret not—we’ve got you covered. Start off your journey with a fueling of caffeine and finish off in a historic battlefield. It doesn’t get any better than a journey through Maryland. Below you’ll find a fantastic route to get you started on your next Maryland road trip. 

1. Get your caffeine fix at Zeke’s Coffee

For this trip, we’re going to start out by going west from Baltimore, Maryland’s largest city. But before you hit the road, stop by Zeke’s Coffee for a delicious cup of joe to fuel up. You’ve got a big weekend ahead of you.

View this post on Instagram

A post shared by Zeke's Coffee - Baltimore (@zekescoffeebmore) on

2. Drive a short distance to the Baltimore Basilica

So this stop doesn’t require much of a road trip, but when in Baltimore, it would be silly not to stop by the Baltimore Basilica. It is America’s first Catholic cathedral constructed in the United States and is an architectural marvel. 

3. Eat a hearty lunch at Dutch’s at Silver Tree Restaurant

From Baltimore, drive three hours west to Oakland, Maryland, where you’ll stop for lunch at Dutch’s at Silver Tree Restaurant before heading out to your next destination. Dutch’s is a rustic restaurant with casual lunch options for every taste.

Dinner was fantastic. #crabcakes #crabimperial #shrimp #scallops #lobstertail #bakedsweetpotato #DeepCreek

A post shared by Michael Chen (@mchen79) on

4. Hike the Swallow Falls State Park Canyon Loop Trail

After lunch, travel the short distance to the Swallow Falls State Park. The park is known for its three majestic falls and easy, relaxing hiking. We recommend the Canyon Loop Trail, which will take you along the Youghiogheny River.

Days like these...💭 #daytrip #daydreaming 🏞 #runnergirl #optoutside 📸 @jinxcy

A post shared by Healthy•ï¼ªï½ï½™ï½†ï½•ï½Œ•ï¼£ï½ï½Žï½†ï½‰ï½„ent🍍 (@rebeccamichele77) on

5. Pick apples at Garden Hour Orchards

After your hike, take a relaxing drive to Smithsburg, Maryland, where you’ll stop at Garden Hour Orchards to pick apples. Call ahead to make sure they have full availability and that you’ll arrive in time to enjoy their many different apple varieties.

A post shared by Lauren (@laurgabrie) on

6. Take a haunted self-guided tour of Hagerstown

Head over to the nearby Hagerstown, Maryland, for an evening of haunted fun. Miller’s Church, just over five miles away, is said to have been taken over by devil worshippers. Go ghost hunting at the Maryland Theatre and Johnathan Hager House. The list goes on and on.

7. Relax at Benny’s Pub

Assuming you make it back without any undue hauntings or demon possessions, stop in at Benny’s Pub for great food and a few drinks. For over a decade, Benny’s has provided classic pub fare, unique dinner specials, and live music. Eat and drink like a local at Benny’s.

One of these days Im going to start a Steak and Cheese show.....

A post shared by One Room Media (@oneroommedia) on

8. Retire to Stoney Creek Farm for the night

Take a 20-minute ride from Hagerstown to Boonsboro, Maryland, and spend the night at Stoney Creek Farm. The Stoney Creek Inn is a charming cabin with modern amenities but many callbacks to the past. It is the perfect location to spend the night.

9. Brunch at the Old South Mountain Inn

You can always stay at the Stone Creek Inn for delicious breakfast options, but if you’d prefer to head into town, then we recommend brunch at the Old South Mountain Inn. Established over 270 years ago, the Inn is set in a colonial-era home and offers a robust Sunday buffet brunch.

View this post on Instagram

A post shared by Andrea K. (@andreakettermanifbbpro) on

10. Take in a little history at the Antietam National Battlefield

The Battle of Antietam in 1862 halted the Confederate Army’s northern march and led to President Lincoln’s Emancipation Proclamation. End your Maryland road trip at the 3,000-acre battlefield park, take in the scenery, and remember the sacrifices our ancestors made so we could enjoy fantastic road trips like the one you just took. 

Select a Maryland town to find the Best Things-To-Do and Places To Go around you
Best Things To Do Near You
Enter City / State or Zip code below
Best Places To Go Near You
Enter City / State or Zip code below
Select your town to find the Best Things-To-Do and Places To Go around you:

Allegany County

Anne Arundel County

Baltimore County

Baltimore City County

Calvert County

Caroline County

Carroll County

Cecil County

Charles County

Dorchester County

Frederick County

Garrett County

Harford County

Howard County

Kent County

Montgomery County

Prince Georges County