15 Best Small Towns in Maryland for a Weekend Escape

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You will find a plethora of amazing destinations in Maryland and one thing the state does well are small towns! These are the best small towns in Maryland to visit this year.

Small towns in Maryland
Small towns in Maryland

We selected Maryland small towns that span the state – from coastal villages and towns to ones nestled in the forests… and beyond!

Did we miss any cute towns in MD? Let us know in the comments if so – thanks!

Best Small Towns in Maryland

Ellicott City

Ellicott City, founded in 1772, is home to the country’s oldest surviving railway station and is one of the state’s most historic towns and the best places to visit in Maryland

The Ellicott City Station is now a museum that is built from blocks of locally quarried granite and features a gabled roof.

Ellicott City
Ellicott City

In the town, and especially on Main Street, there are more than two hundred 18th and 19th-century buildings. You will also find several local shops, boutiques, and an array of stunning houses.

Visit the Wayside Inn B&B, where according to rumors, General George Washington once stayed in, or shop at Historic Savage Mill, a former cotton mill that has been turned into an eclectic mix of shops, galleries, and restaurants.

St. Mary’s City

This former colonial town was Maryland’s first European settlement and capital. It is the fourth-oldest permanent English settlement in the US. Today, the place is one of the ideal vacations for history enthusiasts, who can witness history firsthand.

St. Mary’s City is the ultimate place to learn about history in a fun way! You can visit some of the public living history museums, where workers are dressed in period clothing and recreate historical events. Visitors are also welcomed to see the restored original colonial settlement. 

St. Mary's City - Editorial credit- Regine Poirier - Shutterstock.com
St. Mary’s City – Editorial credit- Regine Poirier – Shutterstock.com

Another interesting thing to explore is a working colonial farm and a working replica of the Dove Sailing Ship, which is one of the two original settlers’ ships that established the Maryland Colony.

Bel Air

Bel Air is a small town located 45 minutes north of Baltimore in northern Maryland. 

The most popular touristic things to do in Bel Air include afternoon shopping at one of the many boutiques, enjoying a beer at one of the local breweries, or eating at one of the many delicious restaurants. 

Bynum Run Creek in Bel Air
Bynum Run Creek in Bel Air

In the past, Bel Air, like many other small towns on the east coast, was a stop on the subway system.

By booking a tour of the Hays-Heighe house on Harford Community College’s campus (only a few miles from downtown Bel Air) you’ll have the perfect opportunity to learn about the town’s heritage.

St. Michaels

One of the most beautiful small towns in Maryland is St. Michaels (or Saint Michaels). The tiny town is situated in Talbot County and has merely just over one thousand residents!

St. Michael's
St. Michael’s

The name came from the parish that settled there in 1677 as the church was known for luring in settlers who wanted to grow tobacco and get into shipbuilding.

A popular attraction in St. Michaels is the Chesapeake Bay Maritime Museum. You can find several historic bay vessels here and it is a National Historic Landmark and definitely worth visiting when in town!

You can also find a 19th-century grist mill in the town called Saint Michaels Mill. It, too, is on the US National Register of Historical Places and has been since 1982.

Mount Airy

Mount Airy is the place where visitors are welcomed to enjoy wine from some of the best wineries in Maryland. 

It’s a small town in central Maryland that is about 45 minutes from Baltimore and Washington, D.C. Popular activities there are a little retail therapy at specialty boutiques, visiting art galleries along the main street, or grabbing something to eat at one of the nearby bistros and cafés.

Mount Airy
Mount Airy

Local wineries are located within a few minutes from the downtown area. If you want to have wine tasting as well as enjoy some live music, you can consider visiting Elk Run Vineyards or Linganore Winecellars wineries. 

Oakland

Oakland is a perfect place for a nature getaway. The small Maryland town is a former railroad town in Garrett County, which is now home to a historic and restored B&O railroad station.

There, the trains are still running on the tracks through the station in times of special events. 

Swallow Falls State Park in Oakland
Swallow Falls State Park in Oakland

If you’re a train enthusiast, the Oakland B&O station is a must-see! Visiting Swallow Falls State Park is yet another interesting site to stroll around, but don’t forget to bring your walking shoes with you.

Alternatively, you can arrange to play a round of golf at Lodestone Golf Club, go horseback riding at Circle R Ranch, or get a boat rental from Brill’s Marine Service. 

Berlin

A small town known for its picturesque main street, Berlin is spotted about 10 miles from Ocean City in the countryside in eastern Maryland. Many think that the name is associated with Germany’s capital; however, the story is that it is a variation of Burleigh Inn, an old tavern in town.

If you’re in favor of spending some time at the beach, go to spectacular Assateague State Park or Dr. Shred’s Surf Adventures.

Wild horses in Berlin
Wild horses in Berlin

When visiting downtown Berlin, consider taking your camera with you to take some shots of Main Street’s old buildings while shopping at Burley Oak Brewing Company or Maryland Wine Bar.

Berlin is also where you can enjoy a variety of outdoor activities all year long, from concerts in the park to the famous peach festival that takes place in the fall.

Monkton

Located in Baltimore County, Monkton is a great option if you’re looking for a rural type of getaway. The cute Maryland town is full of sprawling farmland, horse farms, and historic old houses.

If you get to Monkton, you can’t miss Ladew Topiary Gardens. There are 22 acres of award-winning gardens, where you’re free to take pleasure from a walk in nature. Also, be on the look out for a lovely historic manor house when visiting this site. 

Sunflower fields in Monkton
Sunflower fields in Monkton

There are many trails in the park for hiking, but the Northern Central Railroad Trail is one of the rarer ones. It passes through Monkton Station and up to the Pennsylvania border (it also features an abandoned railroad).  

Hampstead

Hampstead is located in Carroll County and was first called Spring Garden. Due to its fertile lands, the town was originally settled by the English and was an agricultural center. 

Nevertheless, the sleepy farming community has now awakened to find itself in a modern town, which constantly welcomes a lot of visitors!

Pretty Boy Reservoir Dam in Hampstead
Pretty Boy Reservoir Dam in Hampstead

Some of the most visited places here are Leister Park and Cascade Lake (where you can also go swimming by the way). 

Thurmont

This is a perfect getaway for outdoor and art lovers! With the motto of “The Gateway to the Mountains”, Thurmont is located in Frederick County, quite close to the Pennsylvania border in the northern part of Maryland.

The town is adjacent to two state parks, which makes it full of natural, jaw-dropping sights. The largest cascading waterfall in Maryland can be found at Cunningham Falls State Park.

Loys Station Covered Bridge in Thurmont
Loys Station Covered Bridge in Thurmont

Also, just a short distance from Thurmont is the Catoctin Mountain Park, which includes the edge of the Appalachian Mountains. 

The main town is beautiful, and unique with its charming red-brick buildings and a plethora of small, locally owned businesses.

If you happen to be there at the right time, you can catch The Catoctin Colorfest, which is a arts and crafts festival, taking place there annually. This is also one of the best day trips from Frederick!

Eastport

Having the best views of Annapolis’ best landmarks, Eastport offers a relaxed and nonchalant atmosphere of a small town.

The town promises sights that you won’t find in any other place in the US. Eastport is where you can enjoy the views of the Naval Academy, rent a canoe or kayak for sights of the Harbor, or learn about our watermen’s history at the Annapolis Maritime Museum.

Eastport - Editorial credit- MeanderingMoments - Shutterstock.com
Eastport – Editorial credit- MeanderingMoments – Shutterstock.com

Head out to Third and Severn, get a kayak and spend a day on the water, or go to the Maritime Museum. Make sure you’re not missing out on any outdoor concert or festival, as Eastport is known to host pirate ship adventures, outdoor concerts, and oyster festivals.

Crisfield

Famous as the “Seafood Capital of the World”, Crisfield is a town in Somerset County, located on the Tangier Sound on the Chesapeake Bay. Many say that seafood here is really amazing. In fact, there are a few seafood restaurants across the country that carry the city’s name!

The town’s economy has suffered as many Chesapeake Bay industries have somewhat declined but it is maintaining tourism annually as people want to explore the renowned small MD town.

Crisfield
Crisfield

When in Crisfield, you can participate in festivals such as the National Hard Crab Derby, rent a boat to go and explore Smith and Tangier Islands or get into the Janes Island State Park, known for its beautiful marine and birdlife. 

Also, an interesting activity there is visiting the J. Millard Tawes Crab and Clam Bake or the Scorchy Tawes Pro-Am Fishing Tournament to see a real crab and clambake. 

New Market 

New Market, otherwise known as “Antiques Capital of Maryland”, was set when trade routes were established among Baltimore and Frederick.

A lot of people visit New Market to see and shop at the town’s unique boutiques. A place to start off your day is on Main Street, where you’ll enjoy an abundance of antique shops, several charming restaurants, and cafés. 

It’s worth visiting this town even only for its two famous annual festivals that highlight what life in the 18th and 19th centuries was like. “Christmas in New Market” is being held in December, and “A Day in New Market” in May. 

Leonardtown

Leonardtown is yet another hub for seafood lovers and is located in St. Mary’s County.

Check out the cultural sites of the area to get acquainted with the town’s rich history, architecture, and heritage. Leonardtown offers a great range of sights and activities that will both inform and entertain visitors.

Leonardtown
Leonardtown

One of Leonardtown’s most well-known events is the national oyster-shucking championship, held every year at the St. Mary’s County Fairgrounds.

It also hosts family events such as the First Friday, when historic Leonardtown’s art galleries, cafes, gift shops, restaurants, antique shops, and bookstores open their doors to showcase local artists and offer specials. 

Chesapeake City

Chesapeake City is a town located in Cecil County, with a very small population (673, according to the 2010 census).

There are many old homes from the 1800s that have been turned into bed and breakfasts, restaurants, and the local historical museum. One of the famous tourist attractions there is C&D Canal Museum, where you can learn more about the canal that built Chesapeake City. 

Chesapeake City
Chesapeake City

Hiking enthusiasts should get themself to the Ben Cardin Recreational Trail which stretches along the banks of the Canal eastward and reaches up to the Delaware River. 

While it is illegal to use anything without an engine in the canal, it is possible to kayak/canoe/SUP down the Bohemia River nearby. Also, Scotchmans Creek is another great place to do so!

What are the best small towns in Maryland that we missed on the list? Let us know in the comments! Thanks!

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39 thoughts on “15 Best Small Towns in Maryland for a Weekend Escape

    • Megan Starr says:

      ahhhh I will definitely need to check out north east next time I am around so I can add it here! thanks for the tip (googling it now!)

  1. Margaret Smith says:

    This article mixed up St. Michael’s with Solomons. The Anne Marie Sculpture Garden is in Solomons, while St. Michael’s is in Talbot County.

  2. Lynn Mitchell says:

    Great article highlighting some towns we haven’t been to yet. But wild ponies in Berlin? Aren’t they on Assateague/Chincoteague? I’d suggest considering the small towns of Chestertown and Rock Hall on the Eastern Shore. Two different vibes. Chestertown has Washington College, dates back to early 1700s, has some sort of festival every month and a great farmer’s market on Saturday mornings. Rock Hall is at the entrance to the Chesapeake Bay, is a boater’s paradise, has a well regarded live music venue, fantastic seafood restaurants and a laid back summer vibe. Its Pirates and Wenches weekend in August is always a hoot. Best of all, the towns are close enough together to do both in the same trip.

  3. Norma McDonald says:

    You missed Havre de Grace, a historic and beautiful small town. It boasts a boardwalk for walking near the water, sighting waterfowl, a historic lighthouse, many small shops, b & b’s, good restaurants, a lovely park, marina, and also several festivals throughout the year. Additionally Union St. is home to many old, Victorian houses beautifully kept.

    • Megan Starr says:

      I totally did miss Havre de Grace – and I am ashamed to say I have actually been there!! Thanks so much for the note and I will put it on there when I get around to updating the guide in the future and adding some of the cool places I missed!!

      • Cynthia Shelton says:

        HdeG was also in the running as the capital. Washington D.C. was decided on, but just think of the impact it would have been to our state.

        • Megan Starr says:

          Oh wow I had no idea!!! It is so crazy to think of how different things would have been if HdeG was picked 😀

      • Linda Brangenberg says:

        The thing that gets me curious is what is the reason that Easton MD is mostly excluded from these lists of the Best towns in Maryland. It hits all the bells and whistles, food mecca of the area, arts and culture with several seasonal festivals that draw visitors from the Mid Atlantic region and beyond. We had lived there for over 8 yrs and found it to be beautiful and culturally fulfilling.

  4. Joyce Teat Dalto says:

    Rock Hall, Maryland is definitely an awesome small town for a spring, summer, or fall destination. Great restaurants throughout the town, live music, biking, hiking, and all the wonders of the Chesapeake Bay.

    • Megan Starr says:

      You are definitely not the first person to mention Rock Hall for being so cool! It is so funny that these places are often overlooked in MD – the state really does have a nice mix of places for being so small! Thanks for the comment 🙂

  5. Michael Nazelrod-Woodward says:

    Brunswick Maryland is a beautiful small town filled with history. From its rich history as a canal town along the C&O Canal to being an important railroad hub for the B&O Railroad Brunswick is a must stop and see on any travel through Maryland!

  6. CHERYL v GREEN says:

    The towns mentioned in this article are not very racially friendly especially Bel Air Maryland, it’s a sundown town and ppl of color are not welcome, please ppl of color be cautious when visiting these town the ppl there have gone to great lengths to exclude ppl of color from this areas that are name in the article..

    • Megan Starr says:

      Thanks so much for mentioning this, Cheryl. I really appreciate getting an alternative perspective on this. If you have any towns you recommend that are a better option for POC to visit, please let me know. I would love to mention them here and update this article with this information.

  7. Diane Krell says:

    Thanks for including my hometown, Mt. Airy. But now I live very close to Solomon’s Island and Solomons, right next door to each other in Calvert Co. They’re where the large Patuxent River meets the Chesapeake Bay. So there’s boating, shops, restaurants, and the Marine Meritime Museum with a lighthouse to tour plus live sea animals and otters. The Patuxent Air Museum nearby across the river in St Mary’s Co 5 miles away boasts many planes (helicopter, Osprey, mock-up of the Wright Bros. plane with them aboard) and a MIG cockpit! (Also a plantation to tour, Sotterley, about 5 miles).

    • Megan Starr says:

      Aw thanks so much for your comment!! And I feel so horrible because all of my years living in VA and the region, I never really explored the eastern part of MD all that much and I am starting to realize that was a major mistake… especially since there are OTTERS!

      Thanks so much for your tips! Added to my list for sure and hopefully other travelers reading here!

  8. daniel katz says:

    Centreville is a town you can’t miss with its magnificent old court house queen ann’s plaza the historic warf in the corsica river with its captain houses its second to none public library and some of the most beautifull houses like the museum tucker house the bordley house and many more and dont miss o’shucke irish pub and restaurant with its one of a kind trinidad chef,mama mia italian live music in weekends and doc’s seafood bar

  9. Pam Cotter says:

    Eastport is not a small town in MD. It is a neighborhood in the city of Annapolis, our state capitol. You missed Annapolis all together.

    • Megan Starr says:

      Thanks! If you noticed, ‘small towns’ is just a generic term for villages, towns, small cities, neighborhoods, etc used on this guide as being extremely detailed was too long in the title 🙂 Either way, Eastport is most definitely a gem of a place! I didn’t put Annapolis because most people know about it (tried to keep it somewhat lesser-known places for out-of-staters!)

  10. Tamara Silva says:

    Another town which I love is of course Ocean City, MD. It is a great place to go down to the beach, get a crab dinner, get a bunch of souvenirs, go clothes shopping in the outlets nearby.

    • Megan Starr says:

      You had me at Maryland crabs 😀 I do love Ocean City even though it seems as though millions of others do as well during the summer months haha!!! 🙂

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