We’re always on the lookout for small towns in Maryland. The following 10 spots are some of the most picturesque, sure to offer you a delightful day full of scenery and small town charm.
- St Michaels
Flickr / Lee Cannon Shops, seafood, and scenery await in St Michaels. If you’re a fan of bed and breakfasts then this spot is the perfect place spend a weekend.
- Solomons
Flickr / Chris Williamson This southern Maryland spot is surrounded by water views. From sunrise to sunset, you can expect to witness beautiful sights at every turn.
- Havre de Grace
Flickr / Mark Head here for boutiques, eateries, and then pay a visit to Concord Point Lighthouse. This place is uniquely different.
- Berlin
Flickr / Philip N Young Berlin was named America’s coolest small town by Budget Travel a few years back for its events, town pride, and things to do. Be sure to also visit the nearby Assateague Island while you’re in the area.
- Oakland
Flickr / Lindley Ashline If it’s mountain views you crave then head to Oakland. This western Maryland town is especially picturesque during autumn.
- Chesapeake City
Flickr / Larry Wilder Chesapeake City is nestled along the C&D Canal so you can be sure that the sights are enchanting. One of the coolest things about the town is being able to watch ships pass by day and night.
- Chestertown
Flickr / Michel G. It doesn’t get much more charming than historic Chestertown. If you truly want a one of a kind experience then check out their Harry Potter festival this October.
- Sykesville
Jamie Alvarenga / Only In Your State Like Berlin, this town was also recently named America’s coolest small town. The downtown area full of shops is like taking a step back in time.
- Oldtown
Flickr / Jimmy Emerson, DVM This canal-side town offers gorgeous views year-round. If you’re a lover of history, you’ll want to check this place out.
- Oxford
Flickr / Jeff Weese Oxford is underrated but deserves your attention for many reasons. The inns here are delightful and the water views are perfect for a summer day trip.
When it comes picturesque small towns in Maryland, this list just scratches the surface. What are some of your favorites? Feel free to share below.
Flickr / Lee Cannon
Shops, seafood, and scenery await in St Michaels. If you’re a fan of bed and breakfasts then this spot is the perfect place spend a weekend.
Flickr / Chris Williamson
This southern Maryland spot is surrounded by water views. From sunrise to sunset, you can expect to witness beautiful sights at every turn.
Flickr / Mark
Head here for boutiques, eateries, and then pay a visit to Concord Point Lighthouse. This place is uniquely different.
Flickr / Philip N Young
Berlin was named America’s coolest small town by Budget Travel a few years back for its events, town pride, and things to do. Be sure to also visit the nearby Assateague Island while you’re in the area.
Flickr / Lindley Ashline
If it’s mountain views you crave then head to Oakland. This western Maryland town is especially picturesque during autumn.
Flickr / Larry Wilder
Chesapeake City is nestled along the C&D Canal so you can be sure that the sights are enchanting. One of the coolest things about the town is being able to watch ships pass by day and night.
Flickr / Michel G.
It doesn’t get much more charming than historic Chestertown. If you truly want a one of a kind experience then check out their Harry Potter festival this October.
Jamie Alvarenga / Only In Your State
Like Berlin, this town was also recently named America’s coolest small town. The downtown area full of shops is like taking a step back in time.
Flickr / Jimmy Emerson, DVM
This canal-side town offers gorgeous views year-round. If you’re a lover of history, you’ll want to check this place out.
Flickr / Jeff Weese
Oxford is underrated but deserves your attention for many reasons. The inns here are delightful and the water views are perfect for a summer day trip.
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