When you think of Maryland, you probably think of Baltimore, Columbia, and Germantown. Even though these are amazing places to visit, the Old Line State’s true charm lies in its small towns. The stories they tell through history, the charm you see in their architecture – all the features make them irresistible to travelers. People love them for their unhurried pace, welcoming atmosphere, and strong character, and no wonder they are popular among tourists. In this post, we’ll guide you through some small and cute towns in Maryland, and who knows – you might fall in love and decide to move there.
What makes a town cute? How do we make the list of small and cute towns in Maryland?
Before we continue to the list, we want to mention all the characteristics these locations share, and that we used to create this unique list. Small, cute towns usually have:
- Historic architecture – old buildings with brick facades and strong cultural identity.
- A charming downtown that usually has a pedestrian zone, and it’s dotted with local cafes and shops.
- Plenty of local cafes, restaurants, and shops, where owners know the names of their customers and create a unique, welcoming feel.
- Beautiful nature surrounding the place – usually you can easily reach a mountain, a park, a riverside, etc., and enjoy the picturesque surroundings.
- Slow pace of life – with less traffic and tourism, small towns usually feel a lot slower compared to bigger cities. People spend less time in their car, but arrive home earlier and go out with their family.

Berlin - 111 miles from Annapolis
This tiny town is known to be Maryland’s best-kept secret, and for good reason. Also named ‘the coolest small town in MD’, Berlin will amaze you with its historic charm, beautiful architecture, great dining, and entertainment options. So if you’re looking for a ‘cool town near me’ for a weekend getaway, look no further. Located just 10 miles away from Ocean City, this lovely town is sheltered from the crowds, yet relatively close to everything you might need.
Berlin boasts a very vibrant Main Street, filled with shops, cafes, and restaurants. Locals and visitors have plenty to do here, as there are plenty of art galleries, live music shows, and unique events all year round. You can head downtown and go shopping in six different districts, visit the Mermaid Museum, admire local art, and when you get tired and hungry, hit some of the great Berlin restaurants. Try Rayne’s Reef Soda Fountain and Grill for some classic diner experience, or get a traditional BBQ at Blacksmith. Finally, try a local craft beer at some of the breweries, such as Burley Oak Brewing Company or The Buzz Meadery, and their iconic mead.

Havre de Grace - 41 miles from Baltimore
This charming small town, located north of Baltimore, is known for its waterfront area, scenic views, parks, festivals, and so much more. Nestled where Chesapeake Bay meets the Susquehanna River, Havre de Grace is a popular recreation spot and a favorite among tourists coming to this area.
This lovely town boasts a vibrant and beautiful downtown and a romantic waterfront area with the famous Concord Point Lighthouse. It’s a beautiful location perfect for watching sunsets, enjoying nature, and it’s a popular spot for special moments such as an engagement. For some good food, check out Water Street Restaurant, Tidewater Grille, and the Promenade Grille, and for some history, check out Lock House museum and the Havre de Grace Decoy Museum. A fascinating fact – Havre De Grace lost the title of the capital of the nation by only one vote, which is hard to imagine these days, comparing Washington, DC to this lovely, but tiny town.
Boonsboro - 17.7 miles from Frederick
Boonsboro was founded in 1792, and its history is not detailed or long. However, this tiny city is one of the top small, cute towns to visit when in Maryland. Despite its size, the city has plenty of charm and character to make sure you fall in love with it the moment you arrive.
Is there anything to do for fun in Boonsboro? Well, for sure! Check out Crystal Grottoes Caverns for some good-quality tourist time, and experience an underground wonderland. For a history lesson, visit the Antietam National Battlefield. This is a must-see for everyone who wants to find out more about American history, as it’s an extremely important historic spot.
Bel Air - 32 miles from Baltimore
The heart of Harford, Bel Air is a small yet lively town located in the north of Maryland. It perfectly blends old and modern, and you can see that in the architecture, culture, and the community of this lovely little town. It started as a very small community, and it expanded over the years, keeping its small-town charm. Tree-lined streets, local shops, and historic buildings make this place a top attraction in the area. Locals love it for its perfectly balanced size. Bel Air is small enough to be walkable, peaceful, and safe, but it still includes plenty of amenities, entertainment, and dining options.
You might think this is a small town and you’ll have nothing to do here. Well, you’d be wrong. Here are the main Bel Air attractions:
- Go hiking at the Ma and Pa Trail, or use a bike to explore the surrounding woodland and creeks.
- For those who enjoy a piece of history, there’s Liriondenron Mansion, built in 1898, and Tudor Hall, a boyhood home of John Wilkes Booth.
- For some lively entertainment, try Jurassic Gold and Arcade or Crabby Axe Throwing for some real fun.
- There are farmers’ markets, cafes, and local breweries you can browse in Bel Air, and get to know the true spirit of this lovely small town.

Ellicott City - 12.5 from Baltimore
Marylanders truly adore this lovely place for a number of different reasons. Firstly, there’s a lovely downtown area with plenty of charming little buildings in different colors. Ellicott City is located on a hill, so there are many scenic views of the area, perfect for taking pictures.
Over the weekends, you’ll find that this lovely town gets pretty busy, with people coming over to enjoy local cafes and restaurants, go shopping, and more. Some of the top attractions include Thomas Isaac Log Cabin, B&O Ellicott City Station Museum, and Benjamin Banneker Historical Park and Museum.
Ready to explore Maryland?
Maryland is one of the states filled with small and cute historic towns worth visiting. We only named a few but we are sure there are plenty more to visit and see. Apart from having cute and quaint towns, Maryland is one of the top locations with a booming job market, amazing food, beautiful beaches, rich history, and cultural diversity. It’s a state where you can enjoy all four seasons and put your kids through excellent schools. The state seems to have it all. After visiting these lovely small towns, you might decide to make one of them your permanent home – and if that happens, our moving team will support you in this process. You can get premium moving services at reasonable prices, and make Maryland your new home in no time.



