Historic Maryland Fall Road Trip Route

Zeke’s Coffee, Baltimore, MD

For this trip, we will start out by going west from Baltimore’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.

Baltimore Basilica, Baltimore, MD

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. 

Dutch's At Silver Tree Restaurant, Oakland, MD

From Baltimore, drive three hours west to Oakland, 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.

Swallow Falls State Park, Oakland, MD

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.

Gardenhour Orchards, Smithsburg, MD

After your hike, take a relaxing drive to Smithsburg, Maryland, where you’ll stop at Gardenhour 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.

Millers Church, Hagerstown, MD

Head over to the nearby Hagerstown 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.

Benny’s Pub, Hagerstown, MD

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.

Stoney Creek Farm, Boonsboro, MD

Take a 20-minute ride from Hagerstown to Boonsboro 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.

Cooper's Hawk, Annapolis, MD

Taste the finest of the world without leaving your seat. Executive Chef is taking diners on an inspiring culinary journey with a contemporary American menu and 110 exceptional fusion dishes. With carefully paired wines labeled by bin number, each plate is created with peak-of-season ingredients and made fresh in the scratch kitchen. Taste the globe in one bite.

Antietam National Battlefield, Sharpsburg, MD

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. 

Key Insights at a Glance

• Start your journey with a cup of coffee at Zeke's Coffee in Baltimore.
• Visit the Baltimore Basilica, America's first Catholic cathedral.
• Stop for lunch at Dutch's at Silver Tree Restaurant in Oakland.
• Explore Swallow Falls State Park for hiking and waterfalls.
• Pick apples at Gardenhour Orchards in Smithsburg.
• Experience haunted sites in Hagerstown like Miller's Church and the Maryland Theatre.
• Dine at Benny's Pub for local food and drinks.
• Stay overnight at Stoney Creek Farm in Boonsboro.
• Enjoy a culinary journey at Cooper's Hawk in Annapolis.
• End your trip at Antietam National Battlefield in Sharpsburg.