The following small towns in Maryland 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!
January - Thurmont
Andrew Bain / Wikimedia Commons 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. Thurmont, MD 21788, USA
February - St. Michaels
Fletcher6 / Wikimedia Commons St. Michaels is one of the best areas in Maryland for a romantic getaway. This little town is full of cozy bed & breakfasts that are perfect for couples. You’ll also enjoy shopping at the local boutiques and chowing down at the delicious restaurants. Saint Michaels, St Michaels, MD 21663, USA
March - St. Mary’s City
Pubdog / Wikimedia Commons 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. Saint Marys City, St Marys City, MD, USA
April - Chesapeake City
Chris Connelly / Flickr 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. Chesapeake City, MD, USA
May - Solomons
Andrew Belair / Flickr 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. Solomons, MD, USA
June - Stevensville
Henk Sijgers / Flickr 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. Stevensville, MD 21666, USA
July - Berlin
Philip N Young / Flickr 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. Berlin, MD 21811, USA
August - North Beach / Chesapeake Beach
Sandu Antonescu / Flickr 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. North Beach, MD, USA
September - Chestertown
Downtown Chestertown Association / Facebook 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. Chestertown, MD 21620, USA
October - Oakland
David Brossard / Flickr 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. Oakland, MD 21550, USA
November - Mt. Airy
Mike Steele / Flickr 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! Mount Airy, Mt Airy, MD 21771, USA
December - Havre de Grace
Doug Kerr / Flickr 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. Havre de Grace, Havre De Grace, MD 21078, USA
What’s your favorite small town in Maryland, and why? Share your thoughts in the comments!
Andrew Bain / Wikimedia Commons
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.
Thurmont, MD 21788, USA
Fletcher6 / Wikimedia Commons
St. Michaels is one of the best areas in Maryland for a romantic getaway. This little town is full of cozy bed & breakfasts that are perfect for couples. You’ll also enjoy shopping at the local boutiques and chowing down at the delicious restaurants.
Saint Michaels, St Michaels, MD 21663, USA
Pubdog / Wikimedia Commons
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.
Saint Marys City, St Marys City, MD, USA
Chris Connelly / Flickr
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.
Chesapeake City, MD, USA
Andrew Belair / Flickr
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.
Solomons, MD, USA
Henk Sijgers / Flickr
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.
Stevensville, MD 21666, USA
Philip N Young / Flickr
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.
Berlin, MD 21811, USA
Sandu Antonescu / Flickr
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.
North Beach, MD, USA
Downtown Chestertown Association / Facebook
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.
Chestertown, MD 21620, USA
David Brossard / Flickr
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.
Oakland, MD 21550, USA
Mike Steele / Flickr
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!
Mount Airy, Mt Airy, MD 21771, USA
Doug Kerr / Flickr
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.
Havre de Grace, Havre De Grace, MD 21078, USA
Ready for even more exploring? Then check out 9 epic mountains in Maryland that will drop your jaw.
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