Throughout 2016, we featured Maryland’s most charming towns worth visiting. Today, we’re compiling the best of the best into one epic list. Stop putting off your plans to explore this great state and make these towns a priority in 2017.
- Chesapeake City
Flickr / David Clow Located along the Chesapeake & Delaware Canal, this quaint town is filled to the brim with charm. Explore the local shops, chow down on seafood, spend a day on the water, or simply watch the ships float by. There’s no place quite like Chesapeake City.
- Sykesville
Jamie Alvarenga / Only In Your State Budget Travel named Sykesville America’s coolest small town in 2016. This spot has a charming downtown area, railroad history, and hosts lots of family-friendly events throughout the year.
- Annapolis
Flickr / Charlie Stinchcomb If you haven’t visited Maryland’s capital, what are you waiting for?! This waterside town is home to the United States Naval Academy and boasts a rich culture and laid-back lifestyle. Be careful when visiting Annapolis; you may never want to leave.
- Boonsboro
Flickr / Talisen History buffs will go gaga for Boonsboro. This town has an abundance of Civil War history, including hosting reenactments. Be sure to also visit Crystal Grottoes Caverns for a surreal experience.
- St. Michaels
Flickr / F Delventhal This little town on the water has everything. Dozens of local shops line the main street area, nautical views abound, and the bed & breakfasts can’t be beat. This place is perfect for a weekend getaway.
- Frederick
Flickr / ehpien Not only is Frederick great for visitors, but it’s also one of the most livable towns in the state. While this space is jam-packed with local businesses, it still retains a quaint charm that’s incomparable.
- Berlin
Wikimedia Commons / Squelle Another Maryland town that has ranked as one of America’s coolest, Berlin’s community is close-knit and full of pride. Main Street is always lively with one-of-a-kind events that you won’t want to miss.
- Solomons
Flickr / Chris Williamson Sprawling water views make this town pleasing to the eye, while fresh seafood will leave your belly satisfied. If you take a day trip here, make sure to stay late to watch the sunset. You won’t regret it.
- Oakland
Facebook / A Great Small Town The western town of Oakland is particularly scenic, especially during autumn. This time brings the annual Autumn Glory Festival and the fall foliage is breathtaking.
- Chestertown
Michel G. If you’ve never been to Chestertown, you’re in for a treat. Stroll the brick-lined streets while perusing the stores and dine at the restaurants that pack big flavor. During fall, the town goes all out for their very own Harry Potter weekend, transforming into a magical village. It’s an experience to remember.
- Havre de Grace
Facebook / Explore Havre de Grace Havre de Grace deserves more attention, as it has a delightful downtown area and residents who truly love the town. There’s always something to do here if you know where to look.
- Williamsport
Flickr / Jerry Edmundson This little town will make you want to get outdoors, whether it’s exploring the C&O Canal trail or taking in historic sights. They don’t make em like this anymore.
How many of these towns have you already visited? Looking for more adventures in 2017? Then check out this list of places to go this year!
Flickr / David Clow
Located along the Chesapeake & Delaware Canal, this quaint town is filled to the brim with charm. Explore the local shops, chow down on seafood, spend a day on the water, or simply watch the ships float by. There’s no place quite like Chesapeake City.
Jamie Alvarenga / Only In Your State
Budget Travel named Sykesville America’s coolest small town in 2016. This spot has a charming downtown area, railroad history, and hosts lots of family-friendly events throughout the year.
Flickr / Charlie Stinchcomb
If you haven’t visited Maryland’s capital, what are you waiting for?! This waterside town is home to the United States Naval Academy and boasts a rich culture and laid-back lifestyle. Be careful when visiting Annapolis; you may never want to leave.
Flickr / Talisen
History buffs will go gaga for Boonsboro. This town has an abundance of Civil War history, including hosting reenactments. Be sure to also visit Crystal Grottoes Caverns for a surreal experience.
Flickr / F Delventhal
This little town on the water has everything. Dozens of local shops line the main street area, nautical views abound, and the bed & breakfasts can’t be beat. This place is perfect for a weekend getaway.
Flickr / ehpien
Not only is Frederick great for visitors, but it’s also one of the most livable towns in the state. While this space is jam-packed with local businesses, it still retains a quaint charm that’s incomparable.
Wikimedia Commons / Squelle
Another Maryland town that has ranked as one of America’s coolest, Berlin’s community is close-knit and full of pride. Main Street is always lively with one-of-a-kind events that you won’t want to miss.
Flickr / Chris Williamson
Sprawling water views make this town pleasing to the eye, while fresh seafood will leave your belly satisfied. If you take a day trip here, make sure to stay late to watch the sunset. You won’t regret it.
Facebook / A Great Small Town
The western town of Oakland is particularly scenic, especially during autumn. This time brings the annual Autumn Glory Festival and the fall foliage is breathtaking.
Michel G.
If you’ve never been to Chestertown, you’re in for a treat. Stroll the brick-lined streets while perusing the stores and dine at the restaurants that pack big flavor. During fall, the town goes all out for their very own Harry Potter weekend, transforming into a magical village. It’s an experience to remember.
Facebook / Explore Havre de Grace
Havre de Grace deserves more attention, as it has a delightful downtown area and residents who truly love the town. There’s always something to do here if you know where to look.
Flickr / Jerry Edmundson
This little town will make you want to get outdoors, whether it’s exploring the C&O Canal trail or taking in historic sights. They don’t make em like this anymore.
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