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.
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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.
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.
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.
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.
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.
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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.
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Allegany County
- Barton
- Corriganville
- Cumberland
- Eckhart Mines
- Ellerslie
- Flintstone
- Frostburg
- LaVale
- Little Orleans
- Lonaconing
- Luke
- Midland
- Midlothian
- Mount Savage
- Oldtown
- Pinto
- Rawlings
- Spring Gap
- Westernport
Anne Arundel County
- Annapolis
- Arnold
- Churchton
- Crofton
- Crownsville
- Curtis Bay
- Davidsonville
- Deale
- Edgewater
- Fort George G Meade
- Friendship
- Galesville
- Gambrills
- Gibson Island
- Glen Burnie
- Hanover
- Harmans
- Harwood
- Linthicum Heights
- Lothian
- Mayo
- Millersville
- Odenton
- Pasadena
- Riva
- Severn
- Severna Park
- Shady Side
- Sherwood Forest
- Tracys Landing
- West River
Baltimore County
- Baldwin
- Boring
- Brooklandville
- Butler
- Catonsville
- Chase
- Cockeysville
- Dundalk
- Essex
- Fork
- Fort Howard
- Freeland
- Glen Arm
- Glyndon
- Gwynn Oak
- Halethorpe
- Hunt Valley
- Hydes
- Kingsville
- Long Green
- Lutherville Timonium
- Maryland Line
- Middle River
- Monkton
- Nottingham
- Owings Mills
- Parkton
- Parkville
- Perry Hall
- Phoenix
- Pikesville
- Randallstown
- Reisterstown
- Riderwood
- Rosedale
- Sparks Glencoe
- Sparrows Point
- Stevenson
- Timonium
- Towson
- Upper Falls
- Upperco
- White Marsh
- Windsor Mill
Baltimore City County
Calvert County
- Barstow
- Broomes Island
- Chesapeake Beach
- Dowell
- Dunkirk
- Huntingtown
- Lusby
- North Beach
- Owings
- Port Republic
- Prince Frederick
- Rose Haven
- Saint Leonard
- Solomons
- Sunderland
Caroline County
- Bethlehem
- Denton
- Federalsburg
- Goldsboro
- Greensboro
- Henderson
- Hillsboro
- Marydel
- Preston
- Ridgely
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Carroll County
- Finksburg
- Hampstead
- Keymar
- Lineboro
- Manchester
- Marriottsville
- New Windsor
- Sykesville
- Taneytown
- Union Bridge
- Westminster
Cecil County
- Cecilton
- Charlestown
- Chesapeake City
- Childs
- Colora
- Conowingo
- Earleville
- Elk Mills
- Elkton
- Georgetown
- North East
- Perry Point
- Perryville
- Port Deposit
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- Warwick
Charles County
Dorchester County
- Cambridge
- Church Creek
- Crapo
- Crocheron
- East New Market
- Fishing Creek
- Hurlock
- Linkwood
- Madison
- Rhodesdale
- Secretary
- Taylors Island
- Toddville
- Vienna
- Wingate
- Woolford
Frederick County
- Adamstown
- Braddock Heights
- Brunswick
- Buckeystown
- Burkittsville
- Emmitsburg
- Frederick
- Ijamsville
- Jefferson
- Knoxville
- Ladiesburg
- Libertytown
- Middletown
- Monrovia
- Mount Airy
- Myersville
- New Market
- New Midway
- Point of Rocks
- Rocky Ridge
- Sabillasville
- Thurmont
- Tuscarora
- Unionville
- Walkersville
- Woodsboro
Garrett County
- Accident
- Bittinger
- Bloomington
- Friendsville
- Grantsville
- Kitzmiller
- Mc Henry
- Mountain Lake Park
- Oakland
- Swanton
Harford County
- Aberdeen
- Aberdeen Proving Ground
- Abingdon
- Bel Air
- Belcamp
- Benson
- Churchville
- Darlington
- Edgewood
- Fallston
- Forest Hill
- Gunpowder
- Havre de Grace
- Jarrettsville
- Joppa
- Perryman
- Pylesville
- Street
- White Hall
- Whiteford
Howard County
- Annapolis Junction
- Clarksville
- Columbia
- Cooksville
- Dayton
- DHS
- Elkridge
- Ellicott City
- Fulton
- Glenelg
- Glenwood
- Highland
- Jessup
- Lisbon
- Savage
- Simpsonville
- West Friendship
- Woodbine
- Woodstock
Kent County
Montgomery County
- Ashton
- Barnesville
- Beallsville
- Bethesda
- Boyds
- Brinklow
- Brookeville
- Burtonsville
- Cabin John
- Chevy Chase
- Clarksburg
- Colesville
- Damascus
- Derwood
- Dickerson
- Gaithersburg
- Garrett Park
- Germantown
- Glen Echo
- Kensington
- Laytonsville
- Montgomery Village
- North Bethesda
- North Potomac
- Olney
- Poolesville
- Potomac
- Rockville
- Sandy Spring
- Silver Spring
- Spencerville
- Suburb Maryland Fac
- Takoma Park
- Washington Grove
- Wheaton
Prince Georges County
- Accokeek
- Adelphi
- Andrews Air Force Base
- Aquasco
- Beltsville
- Berwyn Heights
- Bladensburg
- Bowie
- Brandywine
- Brentwood
- Capitol Heights
- Cheltenham
- Clinton
- College Park
- Colmar Manor
- District Heights
- Edmonston
- Forest Heights
- Forestville
- Fort Washington
- Glenn Dale
- Greenbelt
- Hyattsville
- Landover
- Landover Hills
- Lanham
- Largo
- Laurel
- Mitchellville
- Mount Rainier
- New Carrollton
- Oxon Hill
- Riverdale
- Seat Pleasant
- Southern MD Facility
- Springdale
- Suitland
- Temple Hills
- University Park
- Upper Marlboro
Queen Annes County
- Barclay
- Centreville
- Chester
- Church Hill
- Crumpton
- Grasonville
- Ingleside
- Price
- Queen Anne
- Queenstown
- Stevensville
- Sudlersville
Saint Marys County
- Abell
- Avenue
- Bushwood
- California
- Callaway
- Chaptico
- Charlotte Hall
- Clements
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- Compton
- Dameron
- Drayden
- Great Mills
- Helen
- Hollywood
- Leonardtown
- Lexington Park
- Loveville
- Mechanicsville
- Morganza
- Park Hall
- Patuxent River
- Piney Point
- Ridge
- Saint Inigoes
- Saint Marys City
- Scotland
- Tall Timbers
- Valley Lee
Somerset County
- Crisfield
- Deal Island
- Ewell
- Manokin
- Marion Station
- Princess Anne
- Rehobeth
- Tylerton
- Upper Fairmount
- Westover
Talbot County
- Bozman
- Claiborne
- Cordova
- Easton
- McDaniel
- Neavitt
- Newcomb
- Oxford
- Royal Oak
- Saint Michaels
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- Trappe
- Wittman
- Wye Mills
Washington County
- Big Pool
- Boonsboro
- Brownsville
- Cascade
- Cavetown
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- Clear Spring
- Fairplay
- Funkstown
- Hagerstown
- Hancock
- Keedysville
- Maugansville
- Rohrersville
- Saint James
- Sharpsburg
- Smithsburg
- Williamsport
Wicomico County
- Allen
- Bivalve
- Delmar
- Fruitland
- Hebron
- Mardela Springs
- Nanticoke
- Parsonsburg
- Pittsville
- Powellville
- Quantico
- Salisbury
- Sharptown
- Tyaskin
- Willards