Being from the “Old Line State,” I’ve seen a lot of different towns in Maryland. When the pandemic hit, I decided to get to know this place a bit better and explore different areas that I hadn’t seen before. I’ve been to many, many places here, and these are the ones that stuck out the most to me.

Unlike my other posts, this list is in order of population size. Some of these places are technically cities but have a small-town feel, and don’t have many residences in their downtown/old town areas – so I thought it was still suitable to call them “towns.”

Please note this post does not include towns in Maryland that are on the Eastern Shore! Instead I have them in my post on Maryland Eastern Shore towns.

Havre de Grace, Maryland

History: Havre de Grace is the oldest town on this list, and one of the oldest towns in Maryland. It started in 1695 as the bottom port for a ferry that crossed the Susquehanna River – a ferry that famous people such as George Washington crossed themselves. Because of the ferry, it saw a lot of action during the Revolutionary War and the War of 1812. Since then, the economy has centered on fishing and duck hunting – very evident in today’s town – and, of course, tourism.

Most fascinatingly, Havre de Grace lost becoming the nation’s capital by only 1 vote! It’s hard to imagine that now, since Washington, DC is a large city and Havre de Grace is a tiny town – but they were once in the same playing field.

Today: Havre de Grace is a step into Maryland’s past with many buildings and businesses paying homage to life many decades ago. It has more of a mid-20th century type of feel than like a 19th or 18th century feel. Small but not deserted, and with enough life to be homey.

I actually did not put HdG on my list initially because it’s kind of cute but not stunning. But the small businesses have drawn me back time and time again, and this place has grown on me.

Things to Do: The main attraction of Havre de Grace is the town itself. It’s lined with incredibly cute shops, many of them vintage-inspired, and a few places to eat. It’s quite small so you can cover the town in only a half hour (but be sure to spend more time to stop into stores, get a bite to eat, etc). Concord Point Park and its lighthouse is probably the main place to visit otherwise.

Boonsboro, Maryland

History: Boonsboro is a tiny place with a short history. It was founded in 1792 by cousins of Daniel Boone. The buildings made for makeshift hospitals at the Battle of Antietam and the Battle of South Mountain, but aside from what must have been that terribly exciting time, not a lot has happened in this small town. But that also means it’s stood still in time.

Today: Boonsboro is a tiny, tiny place – but it had just enough charm to make the cut. I particularly loved the old wooden houses. Between a handful of low-key restaurants and some local stores, there’s not a lot to do here, but it does make a good stop if you’re looking for some exciting places to visit nearby. The list is below:

Things to Do: From the town, you can walk to Crystal Grottoes Caverns. These caverns are Maryland’s only publicly open grottoes. I’ve never been – I’m not a cave person – but they got great reviews.

Nearby is Antietam National Battlefield. If you’re unfamiliar with Antietam, you must not be American because it is an extremely important place in American history. The Battle of Antietam was the bloodiest battle of the American Civil War and was also the turning point from when the South was winning to when the North’s luck began to change. It’s a must-see for military history enthusiasts or if you’re looking to learn more about American history.

The lesser-known South Mountain State Battlefield is also very close.

North Beach & Chesapeake Beach, Maryland

I had several homes growing up but my most permanent is here in this place of a small (but growing) population. It was a cute nowhere until only a few years ago when it somehow became a tourist destination. I still love going down to visit.

North Beach & Chesapeake Beach are easily walkable from one another. If you didn’t know otherwise, you’d probably think they were the same town.

History: Chesapeake Beach started as a resort town in the tail end of the 19th century. The allure of the bay as a trip from Washington, DC and Baltimore resulted in a train being built and many steamships pulling in for people to visit daily during the summer months. But it was short-lived. By 1935, the train station was no longer needed and went out of business. For decades, it’s stood as a charming suburb of DC but in recent years, has seen a spike in visitors.

Our claim to fame is that Tom Clancy lived here.

Today: Both North Beach and Chesapeake Beach are adorable shore towns that are growing but still retaining the feel of small-town life. The train and amusement park that used to define the towns are no longer there but we still have our boardwalk, the train station, and a bunch of local businesses. The bay is the true star of the show here.

Things to Do: The main thing to do in North Beach is visit the boardwalk. There’s ice cream and fro-yo places to grab a bite and then you can walk the stretch of the boardwalk – which is what a lot of us locals do. There’s also a wine shop where you can buy wine by the glass and have a drink right there. The beaches are open but in recent years they’ve required non-residents to pay to use the beaches. If you wish, some water sports like kayaking are also recently available at the beach.

In Chesapeake Beach, which is a walk away from North Beach, the popular activity is to go to the water park. Nearby there’s a local tea spot called Butterflies & Wishes which I recommend stopping in if you like tea. They have almost everything! As for beaches, Brownie Beach used to be popular but as of 2024, it’s completely closed to non-residents. I’ll update this post as situations with the beaches change – which is hopefully soon.

Both towns have lots of antique stores that are stuffed to the brim with cool things, so if you like antiquing, this is a great place to be.

I don’t normally recommend restaurants but *the* places to eat if you’re looking for an upscale experience are Baia (my fave) and Hook & Vine. There’s also Vaughan Cheese, best for lunch & snacks. There are lots of other places that are good but not as nice.

Frederick, Maryland

History: Frederick probably has the most interesting history of all these towns in Maryland. Founded in 1762, it was part of the “Great Wagon Road” immigrant trail that started at the Philadelphia port and went all the way down to Kentucky. A lot of German immigrants stopped here and made the community their home, often using mining as their trade. Lots of famous people passed through Frederick, including Abraham Lincoln and Francis Scott Key, and it saw a lot during the Civil War.

Today: Frederick is my absolute favorite place on this list. It’s technically a city but the downtown area has a small-town feel. Frederick has so many dining options, and there are a ton of local stores to visit. My personal favorite is Emporium Antiques, which is a must-visit if you like to go antiquing. They have tons of stalls with tons of price ranges, and many of them have amazing bargains.

Things to Do: Rose Hill Manor Park is an 18th century home serving as a museum for what life was like during that period. Similarly, the Schifferstadt Architectural Museum is a small museum displaying the architecture that was typical of the area during the 19th century.

If you’re interesting in military history, there’s a lot to see in Frederick and the surrounding area. If Frederick downtown area you can walk to the Hessian Barracks from the Revolutionary War and the National Museum of Civil War Medicine. Nearby you can visit Monococy National Battlefield from the Civil War.

For a cute photo stop, Caroll Creek Covered Bridge is only a short drive or a 20-minute walk from downtown Frederick. There are only a handful of covered bridges left in Maryland and this one is very conveniently located.

Ellicott City, Maryland

History: In the wake of the industrial revolution, three brothers with the name Ellicott started mills fueled by the Patapsco River, including sawmills, grain mills, and oil mills, amongst others. After flourishing and becoming a huge place of employment, it became a stop on the B&O Railroad in the early 19th century. It became victim to the frightful Fs: flood and fire. A lot of companies went out of business because of it, though there is still a grist mill there today.

Today: Ellicott City is one of Marylanders’ favorite places and it’s very easy to see why. The old town area is one of the most complete in the entire state. It’s also a city but because of the large land area – the Old Town is decently sized but comparatively quite small. It’s on a hill so the landscape of it is just incredible with lovely views down the city when you get to the top.

Because of the destruction the town’s seen, a lot of the buildings are not original but still very charming. I wouldn’t have really been able to tell. But Ellicott City still sees a lot of flooding. Actually, many people – myself included – think of the word “flood” whenever Ellicott City comes up.

Ellicott City is very busy on weekends, and there’s a variety of different places to eat (mostly cafe-type restaurants) and local stores. I definitely recommend a stop here if you haven’t been before.

Things to Do: The most iconic thing to do is see the Thomas Isaac Log Cabin, which dates to 1780. There’s also the railroad tracks from the B&O railroad, and of course the B&O Ellicott City Station Museum if you’re interested in learning more. There’s also a ton of great street art in the small area that is the city’s old town, so keep an eye out.

A short drive away is the Benjamin Banneker Historical Park & Museum, dedicated to one of Maryland’s most famous Black abolitionists. He was extremely accomplished in academics during his time despite living during the era of slavery.

Nearby Daniels is an abandoned mill town that’s fun to visit. You have to hike a bit through the woods to get there.

Annapolis is very much a city, but it’s still so so charming and often overlooked. You can read my guide here and I highly recommend visiting. For more on Maryland, click here for my MD blog posts

That’s My List of Cute Towns in Maryland!

My journeys through Maryland have led me to recommend these places to visit. I hope I described them well enough to help you make a decision about whether or not to visit, and if you do visit, I hope you have a wonderful time! Like I said, I’ve been to many places but these were the ones that stood out to me.

Do leave a comment with your favorite place to visit in Maryland!

A lot of these places have great antique stores which I’ve mentioned on my post of antique stores. If you like antiquing, go give it a quick read!

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