17 Charming Small Towns in Maryland That You Need To Visit (2024)

Maryland has something to offer both nature lovers and city-goers alike, boasting beautiful east coast coastlines and plenty of charming small towns.

From quaint fishing villages to historic architecture, small towns in Maryland provide the perfect getaway for those looking for a slower pace.

Take a bike ride along the Chesapeake & Ohio Canal National Historic Park, explore the vibrant streets in Takoma Park, or escape to a secluded beach in Assateague State Park—you’ll be amazed by what Maryland’s small, historic towns have to offer.

Maryland is home to an abundance of delicious seafood delicacies from oysters and crabs to clams, rockfish, bluefish and much more.

This unique location provides access to fresh seafood all year round – making it easy for restaurants and other culinary artisans to create flavorful dishes.

To help you decide where to visit, we’ve compiled a list of 17 of the most delightful and beautiful small towns in Maryland.

From traditional fishing villages to colorful downtowns, these small towns have something for everyone.

Whether you are a nature lover looking for outdoor activities or an urbanite looking for a slower pace and a quaint Main Street, small towns in Maryland have sometimes for everyone.

Let’s take a look at all the great places you can visit!

1. Takoma Park

Takoma Park, Maryland is a unique and charming small town that has something to offer all types of travelers.

Whether you are looking for outdoor activities, cultural attractions, or a slower pace of life, Takoma Park has it all.

Takoma Park is often referred to as a “small city within a city,” making it a perfect destination for those who are looking for an urban escape without leaving the city limits.

There are many things to do and see in Takoma Park, from shopping and dining options to outdoor recreation spaces.

Make sure you stop by Takoma Park is Sligo Creek Park.

This park features miles of trails perfect for hiking and biking, as well as plenty of open space and fields where visitors can enjoy picnics and other outdoor activities.

Other attractions include local art galleries, music venues, historic sites and museums.

Takoma Park is also home to several interesting annual festivals such as the International Clowns Festival and the Annual Marching Band Festival.

With its vibrant arts scene, delicious cuisine, unique architecture and friendly locals, Takoma Park should definitely be on your list of places to explore when visiting Maryland!

2. Oxford

With its picturesque views, quaint shops and laid-back atmosphere, Oxford is an ideal destination for travelers looking for a relaxing getaway.

Oxford offers plenty of entertainment options for visitors of all ages.

The town features several museums and historic sites that provide insight into the area’s rich past.

These include the Oxford Museum, which houses artifacts from more than 400 years of local history; the Oxford Historic District, where visitors can explore the streets and beautifully restored buildings to get a feel for what life was like here in the 1800s; and William Blackstone Memorial Park.

The downtown area in Oxford is full of charming shops offering fine wine, clothing, books and handmade crafts – perfect for browsing or buying souvenirs to take home with you.

In addition to its great shopping and dining experiences, Oxford also boasts plenty of outdoor recreational activities including fishing, kayaking, sailing, bird watching and more!

Whether you are looking for a romantic escape or an enjoyable family vacation spot, Oxford has something for everyone – making it an unforgettable destination in Maryland!

3. St. Michaels

With its beautiful waterfront views, delicious seafood restaurants, and numerous recreational activities, St. Michaels is the perfect small town for visitors looking to explore the unique charm of Maryland’s Eastern Shore.

The town of St. Michaels is home to several interesting attractions such as The Chesapeake Bay Maritime Museum and Hooper Strait Lighthouse, offering insight into the area’s rich maritime history.

Both sites provide ample opportunities to learn more about local boat building traditions and other aspects of life on the water in Maryland.

St. Michaels also offers plenty of outdoor activities for visitors to enjoy including fishing, kayaking, sailing and bird watching along its scenic waterfront trails.

The harbor area of town also features several excellent restaurants that serve up delicious local seafood dishes such as crab cakes, oysters and rockfish – perfect for those looking for a tasty meal after a day out exploring!

Whether you are looking for an enjoyable family getaway or a romantic weekend escape, St. Michaels has something for everyone. So, make sure you add this to your “small towns Maryland” checklist.

4. Annapolis

Annapolis, Maryland is a charming small town located on the Chesapeake Bay.

With its rich maritime history, world-renowned sailing destinations, and delicious seafood restaurants – Annapolis is an ideal destination for visitors looking to explore the unique charm of Maryland.

The downtown area of Annapolis is full of historic attractions such as the U.S. Naval Academy, Maryland State House and William Paca House & Garden.

Visitors can also take in some of the city’s fantastic views from up above with a ride on the Annapolis Harbor boat tour.

In addition to its great sightseeing opportunities, Annapolis also boasts plenty of outdoor recreational activities including kayaking, fishing and sailing along its scenic waterfront trails.

The harbor area is home to several excellent restaurants that serve up delicious local seafood dishes such as crab cakes and oysters – perfect for those looking for a tasty meal after a day out exploring small towns.

Make sure you visit this historic town!

5. Havre de Grace

Havre de Grace, Maryland is a beautiful waterfront small town located on the Susquehanna River.

With its picturesque views, rich maritime history and abundance of recreational activities – Havre de Grace is an ideal destination for visitors looking to explore the unique charm of Maryland.

The Havre de Grace downtown area boasts several historical attractions such as Concord Point Lighthouse, Lewis & Clark Trail and The Tidewater Grill Museum, which provide great opportunities for visitors to learn more about the city’s fascinating past.

Those looking for a bit of retail therapy can find plenty of local boutiques to browse in Havre de Grace as well as several charming restaurants worth checking out while you’re there.

6. Chestertown

Chestertown is an idyllic waterfront, small Maryland town located on the scenic Chester River.

With its historic charm, vibrant cultural scene and abundance of outdoor activities – Chestertown is an ideal destination for visitors looking to explore the unique beauty of Maryland.

The downtown area has a wealth of historical attractions such as the William Seefurth Studio, Historic Chesterwood Museum and Garfield Center for the Arts at The Prince.

You can find plenty of local boutiques to browse in Chestertown as well as several delicious restaurants serving up classic American fare worth checking out while you’re there.

7. Berlin

Berlin, Maryland is located in the heart of the Eastern Shore.

With its quaint downtown area, vibrant arts scene and abundance of outdoor activities – Berlin is an ideal destination for visitors looking to explore the unique beauty of Maryland.

The downtown area has plenty of historical attractions such as The Atlantic Hotel and Burley Oak Brewing Company.

You can find plenty of local boutiques to browse in Berlin as well as several delicious restaurants worth checking out while you’re there.

There are also numerous opportunities to enjoy the stunning views over Assateague Island National Seashore via kayaking or paddle boarding trips.

8. Tilghman Island

Tilghman Island, Maryland is a picturesque waterfront town located in the heart of the Chesapeake Bay.

With its tranquil setting, vibrant cultural scene and abundance of outdoor activities – Tilghman Island is an ideal destination for visitors looking to explore the unique beauty of Maryland.

The downtown area has plenty of historical attractions such as The Skipjack Nathan of Dorchester and Knapps Narrows Drawbridge.

There are several local boutiques to browse in Tilghman as well as several delicious seafood restaurants worth checking out while you’re there.

For outdoor enthusiasts, Tilghman Island offers plenty of recreational activities such as fishing, boating, kayaking and bird watching along its scenic trails.

Visitors can also take advantage of its serene coastline with swimming and sunbathing on any one of its idyllic beaches.

9. North Beach

Image: North Beach MD Beach Scene. Mr.TinMD. [CC BY-ND 2.0] via Flickr

With its stunning beachfront, vibrant cultural scene and abundance of outdoor activities – this is an ideal destination for visitors looking to explore the unique beauty of Maryland.

The downtown area has plenty of historical attractions such as The Boardwalk and Chesapeake Beach Railway Museum which provide great opportunities for visitors to learn more about the city’s fascinating past.

For outdoor enthusiasts, this small town offers plenty of recreational activities such as fishing, surfing, swimming and sunbathing on its pristine beaches.

10. Rock Hall

Rock Hall, Maryland is a quaint waterfront fishing village located in the heart of the Chesapeake Bay.

With its tranquil setting, vibrant cultural scene and abundance of outdoor activities – Rock Hall is an ideal destination for visitors looking to explore the unique beauty of Maryland.

The downtown area has plenty of historical attractions such as The Creekside Museum and Historic Main Street.

We love the Main Street in this town!

Those looking for a bit of retail therapy can find plenty of local boutiques to browse in Rock Hall as well as several delicious seafood restaurants worth checking out while you’re there.

11. Snow Hill

Snow Hill, Maryland is a picturesque small town located in the heart of Worcester County.

With its rural town atmosphere, scenic countryside and abundance of outdoor activities – Snow Hill is an ideal destination for visitors looking to explore the unique beauty of Maryland.

The downtown area has plenty of historical attractions such as The Old Court House Museum and Henry Phillip’s bookstore.

12. Solomons Island

Solomons Island, Maryland is a beautiful waterfront town located in the heart of Southern Maryland.

With its tranquil setting, vibrant cultural scene and abundance of outdoor activities – Solomons Island is an ideal destination for visitors looking to explore the unique beauty of Maryland.

The downtown area has plenty of historical attractions such as The Chesapeake Bay Maritime Museum and National Park.

There are plenty of local boutiques to browse in Solomons Island as well as several delicious seafood restaurants worth visiting.

13. Easton

Easton, Maryland is a charming small town situated in the heart of Talbot County.

With its historic downtown, vibrant arts scene and abundance of outdoor activities – Easton is an ideal destination for visitors looking to explore the unique beauty of Maryland.

The downtown area has plenty of historical attractions such as The Easton Waterfowl Festival and Academy Art Museum which provide great opportunities for visitors to learn more about the city’s fascinating past.

14. Cambridge

With its picturesque views, eclectic cultural scene and abundance of outdoor activities – Cambridge is an ideal destination for visitors looking to explore the unique beauty of Maryland.

The downtown area has plenty of historical attractions such as Sailwinds Park and Richardson Maritime Museum.

We think the seafood here is the best among all small towns in Maryland.

15. Assateague State Park

Assateague State Park is a beautiful and secluded barrier island located just south of Ocean City, Maryland.

With its miles of pristine beaches, rich wildlife and abundance of outdoor activities – Assateague State Park is an ideal destination for visitors looking to explore the unique beauty of Maryland.

The park offers plenty of recreational attractions such as its 2-mile-long nature trail and the Assateague Lighthouse, one of Maryland’s best historic buildings.

Those looking for an exciting camping experience can find plenty of campsites available with ocean views and a variety of amenities to make your stay enjoyable.

16. Crisfield

Somers Cover Marina — Image: Somers Cove Marina. Scott. [CC by 2.0] via Flickr

Crisfield, Maryland is a charming town located at the southern tip of the Eastern Shore.

With its rich history, abundance of outdoor activities and picturesque waterfront views – Crisfield is an ideal destination.

The downtown area has plenty of historical attractions.

When it comes to seafood – Crisfield offers an abundance of lip-smacking delicacies from blue crabs to clams, oysters and fish.

This charming little town is built for seafood lovers!

Visitors can take part in their own crabbing or fishing expedition at any one of the local charters or simply enjoy a delicious seafood feast prepared by any one of the popular restaurants in town.

If you happen to visit between Memorial Day and Labor Day weekends – be sure to check out the annual National Hard Crab Derby Festival which celebrates over 100 years of tradition in this small fishing town!

For over a century, Crisfield has been recognized as the “Blue Crab Capital of the World.”

Home to some of the finest seafood in the United States, it’s no wonder why Crisfield is renowned for its unique culinary delights.

For outdoor enthusiasts, Crisfield offers plenty of recreational activities such as sailing, fishing, and crabbing along its scenic waterfront.

Make sure you visit this seafood capital!

17. Ocean City

Ocean City, Maryland is a world-renowned beach resort located just south of the Delaware border.

With its miles of sandy beaches, exciting boardwalk and abundance of outdoor activities – Ocean City has been an ideal destination for visitors looking to explore the unique beauty of Maryland.

The downtown area has plenty of popular attractions such as Jolly Roger Amusement Park and Ripley’s Believe It or Not!, which provide great opportunities for visitors to have some fun.

Other Places To Visit

Janes Island State Park

Janes Island State Park is located in Somerset County, Maryland.

The park encompasses a total of 1,203 acres and offers visitors the chance to explore coastal habitats such as salt marshes, tidal creeks and barrier beaches.

Janes Island State Park offers a multitude of recreational activities such as fishing, crabbing, paddling, camping and hiking.

Beyond that, the park also contains a unique mixture of both natural and historical sites for visitors to enjoy.

Swallow Falls State Park

Spanning over 1,600 acres, the park offers visitors a chance to explore an array of different ecosystems such as rugged mountain peaks, cascading waterfalls and lush forests.

It is home to the state’s highest free-falling waterfall – Muddy Creek Falls – and is filled with plenty of recreational activities such as fishing, hiking, biking, hunting, and camping.

Swallow Falls State Park also features a variety of historical attractions such as the old, covered bridge that crossed the Youghiogheny River as well as an abundance of wildlife.

Check Out A Railroad Town

Cumberland Maryland — Image: Cumberland, Maryland. [CC BY-SA 2.0] via Flickr

Maryland has a rich history of railroad towns, whose presence dates back to the 19th century.

These towns were generally rural, with a majority of citizens relying on railroad-related businesses for their livelihoods.

Today, many of these small Maryland towns feature historical landmarks from this period – such as old railway buildings and stations – that stand as reminders of the region’s colorful past.

Visitors can explore these relics by visiting sites such as the Western Maryland Railroad Museum in Cumberland or the Ellicott City Station Museum in Ellicott City.

Through exhibits and interactive activities, these museums, specifically the one in Ellicott City provide insight into how life was for those who lived and worked in railroad towns during this era.

In addition to its historic airports, some of Maryland’s railroad towns offer plenty of fun attractions and events that are sure to keep visitors entertained during their stay!

From summer festivals featuring live music and entertainment to rail-themed recreational activities like train rides through beautiful countryside – there’s something for everyone in these unique railroad station communities.

So, as you can see, there are plenty of wonderful small towns in Maryland that can offer an escape from big cities along the east coast.

Whether you are seeking living history museums, a quaint Main Street, art galleries, outdoor concerts, historic buildings, or are just traveling with a group of seafood lovers, Maryland is the place to be.

There is something magical about small east coast towns and we hope this list has been helpful for you!

Hey! Want more ideas on the best small towns in the USA? Check these out!

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