Visit These 12 Incredible Charming Small Towns in Maryland, One for Each Month of the Year

We've always believed the heart and soul of Maryland can be found in our small towns. From charming main streets to world-class restaurants, picture-perfect parks, and friendly locals, there's nothing like taking a day trip to a nearby small town. With that in mind, we've hand-picked a dozen small towns in Maryland that are just waiting to be explored! It doesn't matter the time of year -- there is plenty to see and do, from Maryland's western region to the Eastern Shore. Read on to learn more and start planning!

1. January - Thurmont

We love starting the new year with a winter hike, and Thurmont is perfectly located to do just that. This quiet Frederick County town is nestled next to Catoctin Mountain Park, which is full of scenic hikes and overlooks. Need some inspiration? Check out these amazing trails to hike in Catoctin Mountain Park.

2. February - St. Michaels

St. Michaels is one of the best areas in Maryland for a romantic getaway. This little town is full of cozy bed and breakfasts that are perfect for couples. You'll also enjoy shopping at the local boutiques and chowing down at the delicious restaurants. In fact, we've outlined a detailed itinerary for spending the perfect weekend in St. Michaels.

3. March - St. Mary's City

Learn about Maryland's beginnings in historic St. Mary's City. March is a special time here because that's when Maryland Day takes place. It's a pride-filled ceremony that's a must-see in person.

4. April - Chesapeake City

This unique town in Cecil County is right along the Chesapeake and Delaware Canal, making for ship-viewing all day long. Enjoy the peace and quiet here during early spring, along with perusing the area shops and eateries. There's a lot to love about this blink-and-you'll-miss-it kind of small town in Maryland.

5. May - Solomons

As the weather warms, consider heading to Solomons, Maryland. This area offers water views, great seafood restaurants, a small beach, and plenty of pretty photo ops. Don't forget to also check out Annmarie Sculpture Garden & Arts Center to see colorful blooms all around. It really is one of the best warm-weather towns in Maryland.

6. June - Stevensville

Some of the best bay views in the state can be seen from Stevensville on Kent Island. The area parks are oh-so dreamy and you can't beat the local restaurants, many of which offer award-winning crab cakes, and of course, steamed crabs. Whether you explore by foot or by bicycle, you're in for a beautiful time.

7. July - Berlin

This Eastern Shore town is full of character, from its stores to its family-friendly events. There's even a Mermaid Museum! Don't forget that Maryland's famous Assateague Island is also technically in Berlin, where you can visit the beach, see wild horses, and even camp right on the sand.

8. August - North Beach / Chesapeake Beach

The towns of North Beach and Chesapeake Beach are located right next to each other, and right next to the bay as well. Many fishermen head here, as well as folks looking for a relaxing getaway. There's also a local water park, unique restaurants, and resorts.

9. September - Chestertown

This waterside town is full of historic inns and delectable restaurants. Explore the pictured park and area boutiques. Sometimes you can also see historic ships on the waterfront as well. Learn more about why Chestertown is one of the very best small towns in Maryland.

10. October - Oakland

Oakland's annual Autumn Glory Festival takes place every October, and it's a multi-day event! Along with partaking in the festivities, be sure to also drive around, as this is the perfect time for leaf peeping in Maryland's western region. While here, be sure to also check out the scenic Swallow Falls State Park. Plus, did you know that Oakland is Maryland's westernmost town? It also makes for a great winter day trip destination!

11. November - Mt. Airy

Autumn is an amazing time for exploring small towns, as the weather is just right -- not too hot and not too cold. Consider heading to the Mt. Airy area to peruse the downtown businesses, and then be sure to visit the local wineries as well -- there are quite a few!

12. December - Havre de Grace

Havre de Grace has a small-town feel that's big on scenery. We love the local lighthouse and area businesses and just wait until you see this town decked out during the holiday season. Twinkling trees line the streets and there's such a festive feeling in the air.

What's your favorite small town in Maryland? Be sure to share this article with someone you'd love to explore more of Maryland with!

Ready for even more exploring? Then check out 9 epic mountains in Maryland that will drop your jaw.