Maryland is oh-so diverse, with big bustling cities and tiny timid towns. Today we’re focusing on the smaller spots around the state that never seem to change, and we wouldn’t want them to. Check out these 10 classic towns for a peaceful step back in time.
- Smith Island
Flickr / Lee Cannon This inhabited island on the bay is only reachable by boat. Many residents still speak with a traditional accent, truly feeling like you’re in another world.
- Boonsboro
Flickr / Ken Lund This Washington County town is full of history, including a Civil War Museum, historic buildings, nearby Washington Monument State Park, and reenactments throughout the year. This area is a must-visit for any Civil War buff.
- Chesapeake City
Flickr / TCDavis Nestled on the Chesapeake & Delaware Canal, this unique town is like no other. Come and visit the local shops and eateries, stroll the town and see all of the old Victorian houses, and enjoy watching the boats chug along the canal daily.
- Deal Island
Flickr / Justin August For natural wetland views for miles, head to Deal Island. This sleepy little spot is great for walking, biking, and kayaking. Be sure to bring a pair of binoculars for some great bird watching.
- Oakland
Flickr / Ron Cogswell This town is almost as west as you can get in Maryland. It has tons of railroad history and charming town events throughout the year, like the Autumn Harvest festival. The surrounding mountain views aren’t too shabby, either.
- Oxford
Flickr / Michel Alexandre Salim This waterside town has one-of-a-kind things to offer, including a historic ferry ride, charming bed & breakfasts, and a tiny beach known as The Strand. Head here during spring or summer for the best views.
- Burkittsville
Flickr / Gray Lensman QX! This quiet town is known to outsiders as home of the Blair Witch. To locals, it’s just home. Come see the local parks, enjoy a scenic drive, and try out the local gravity hill, known as Spook Hill.
- Port Tobacco
Flickr / F Delventhal Port Tobacco is the tiniest town in Maryland but it’s full of history. Head here to see the old buildings and experience what old town charm is really like.
- Oldtown
Flickr / Jimmy Emerson, DVM Oldtown is a great place to hike right along the C & O Canal. Enjoy the rustic sights and learn tidbits about the past at this remarkable spot.
- Crisfield
Flickr / Scott Known for the freshest crabs in Maryland, Crisfield is a seafood haven on the bay. Many of the local residents are fishermen so you won’t want to miss out on the area restaurants.
For a list of more charming small towns in Maryland, click here.
Flickr / Lee Cannon
This inhabited island on the bay is only reachable by boat. Many residents still speak with a traditional accent, truly feeling like you’re in another world.
Flickr / Ken Lund
This Washington County town is full of history, including a Civil War Museum, historic buildings, nearby Washington Monument State Park, and reenactments throughout the year. This area is a must-visit for any Civil War buff.
Flickr / TCDavis
Nestled on the Chesapeake & Delaware Canal, this unique town is like no other. Come and visit the local shops and eateries, stroll the town and see all of the old Victorian houses, and enjoy watching the boats chug along the canal daily.
Flickr / Justin August
For natural wetland views for miles, head to Deal Island. This sleepy little spot is great for walking, biking, and kayaking. Be sure to bring a pair of binoculars for some great bird watching.
Flickr / Ron Cogswell
This town is almost as west as you can get in Maryland. It has tons of railroad history and charming town events throughout the year, like the Autumn Harvest festival. The surrounding mountain views aren’t too shabby, either.
Flickr / Michel Alexandre Salim
This waterside town has one-of-a-kind things to offer, including a historic ferry ride, charming bed & breakfasts, and a tiny beach known as The Strand. Head here during spring or summer for the best views.
Flickr / Gray Lensman QX!
This quiet town is known to outsiders as home of the Blair Witch. To locals, it’s just home. Come see the local parks, enjoy a scenic drive, and try out the local gravity hill, known as Spook Hill.
Flickr / F Delventhal
Port Tobacco is the tiniest town in Maryland but it’s full of history. Head here to see the old buildings and experience what old town charm is really like.
Flickr / Jimmy Emerson, DVM
Oldtown is a great place to hike right along the C & O Canal. Enjoy the rustic sights and learn tidbits about the past at this remarkable spot.
Flickr / Scott
Known for the freshest crabs in Maryland, Crisfield is a seafood haven on the bay. Many of the local residents are fishermen so you won’t want to miss out on the area restaurants.
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