Best Small Towns In Maryland to Live | 15 Stunning Towns for a Weekend Getaway!

by Tour Squirrel
Published: Last Updated on

Numerous many small towns in Maryland beg to be visited. I just visited Maryland and discovered a few hidden treasures.

Because of its proximity to the ocean, Maryland is known for its seafood and watersports. For many years, Baltimore, the largest city, has also served as a significant harbour.

Small Towns In Maryland

However, for this study, I shall concentrate on Maryland’s tiny towns. There are so many to pick from that it was difficult to limit it to just fifteen! I strongly advise you to include Maryland on your trip itinerary and to take advantage of everything it has to offer.

To assist you arrange the greatest weekend escape, I’ve divided the towns into three categories. Maryland’s towns are all distinct in their way. Historic tiny towns, culinary towns, and places famed for hiking and other outdoor activities are all included!

15 Best Small Towns in Maryland

I divided these little towns into three groups: those with a lot of history, those that enjoy good food, and those who enjoy outdoor activities like hiking. I’ll also tell you when the best time to visit is.

The Most Historic Towns in Maryland

With so many wonderful historic towns to pick from, I’ve narrowed it down to five. There’s something for everyone in these five communities. There are activities for the kids, museums to visit, and the wonderful railway to ride, not to mention all the fascinating history you will learn about.

1. St. Mary’s City

St. Marys City

Maryland is home to a variety of historic communities. St. Mary’s City, on the other hand, is a historic town that served as Maryland’s first European capital and settlement.

It is also the United States’ fourth-oldest permanent English colony. History buffs flock to St. Mary’s City to get a personal look at the region’s past.

This is one of America’s most beautiful historic towns. It contains historical and archaeological information, as well as the incredible story of Maryland’s first-ever capital. With less than 1000 people, it is possibly the smallest town in Maryland with a commercial character.

This small village makes history interesting and engaging. As a result, it’s a fantastic site for kids to learn about tradition and history.

There are living history museums where the employees are clothed in period garb. They’ll also reenact real-life historical occurrences.

If you go to St. Mary’s City, I strongly advise you to visit the rebuilt historic colonial settlement. For everyone interested in history and culture, it is a must-see.

I highly recommend paying a visit to the Dove Sailing Ship, located on a working colonial farm nearby. This is a functioning duplicate of one of the two original Maryland Colony settler ships.

2. New Market

New Market

Baltimore is only 50 minutes away from this little village in Maryland. It’s known as Maryland’s Antiques Capital, making it historically noteworthy.

There are so many unique boutiques to visit that you’ll need at least a weekend to do so. I spent quite a few hours on Main Street by myself. There are a plethora of antique shops, restaurants, and cafés to keep you occupied.

In the Original Playhouse, families will be ecstatic. This Main Street structure houses a children’s museum that will keep the kids occupied for hours.

This museum offers youngsters interactive games that rely on creativity rather than batteries. The museum hopes to improve children’s emotional intelligence and thinking abilities through play.

The months of December and May are ideal for a trip to New Market. Every year during these two months, two well-known festivals take place.

These events are intended to emphasize and replicate life in the 18th and 19th centuries. Christmas in New Market and A Day in New Market are the names of the two festivities, which take place in December and May, respectively.

3. Ellicott City

Ellicott City

This small town is a train enthusiast’s dream come true, as it is home to the country’s oldest railway station. Travellers commonly stop here because it is well-known as one of Maryland’s more historic places.

Historic architecture has always piqued my interest. Around 200 structures from the 18th and 19th centuries line Main Street in Ellicott City. I could have spent hours just roaming about admiring the grandeur of the old buildings and homes.

The Patapsco Female Institute is located in Ellicott City. Between 1837 and 1891, young women were educated at this revolutionary school. It was one of the first schools to introduce female students to disciplines such as chemistry and mathematics. On weekends, a history tour can be taken at the rebuilt site.

A historic cotton mill, the Historic Savage Mill. It has been restored and is now home to many galleries and eateries. Ellicott City also has many modern boutiques and shops, ensuring that everyone has a good time throughout their visit.

4. Pocomoke City

Pocomoke City

This is one of the smaller communities in Maryland’s southern region. It is located just north of the Virginia border. The Pocomoke River, which passes through the city, gives the city its name.

The historic town is well-known for its documentation of the early Maryland colonies, making it a popular destination for historians.

One of the most popular attractions in town is the Delmarva Discovery Centre, which is a museum. In the natural surroundings of the Delmarva peninsula, the museum showcases unique exhibits. It also delves into the history of the region’s first settlements.

The historical exhibits include facts on the Delmarva natives as well as vignettes from their lives. There are items to look at as well.

The habitat exhibits look at Delmarva’s native species. Guests can get up close and personal with the creatures at these exhibitions, which is exciting.

You may also ride a riverboat, see a wigwam, and go inside a beaver dam. This is a museum that has everything for everyone!

5. St. Michael’s

St. Michaels

St. Michaels is a lovely tiny hamlet on Maryland’s eastern shore. It was once a bustling harbour, but now many prefer to spend their weekends lounging by the water.

The current population is slightly over 1000 people; however, it may get fairly crowded during peak season. This is the place to go if you enjoy seaside villages and naval heritage.

The Chesapeake Bay is home to St. Michaels. That is to say; it has a long and illustrious history as a port of call for sailors. The Chesapeake Bay Maritime Museum is located here and features an 18-acre waterfront, spectacular interior and outdoor exhibitions, and a beautiful harbour.

When you visit this National Historic Landmark, you will also be able to see several historic vessels.

Talbot Street is also located in St. Michaels. Local wineries are well-known on Talbot Street. After a day of experiencing the area’s nautical heritage, you may unwind there. Alternatively, take a harbour tour and see the bay!

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Best Places To Visit For Food and Drinks

If you’re a foodie like me, there’ll never be a scarcity of delicious food and beverages in these small communities.

I’ll start with Bel Air and walk through a list of five sites you must see. With an abundance of restaurants, breweries to visit, a variety of craft cocktails to sample, and exquisite wine to sample, you will be spoiled for choice.

1. Bel Air

Bel Air

Bel Air is one of Maryland’s larger communities, and it’s what I’d call gastronomic heaven. If you’re a foodie like me, you appreciate exquisite cuisine, decent wine, and a variety of craft beverages. Bel Air is home to some excellent craft brewers.

The Independent Brewing Company is located on Bel Air’s Main Street. It is one of Harford County’s best breweries. It includes a big taproom and patio where you can sample the brewery’s offerings.

They always have 26 ciders and ales on tap, which change seasonally. As a result, there’s always something fresh to discover.

There are a total of 57 restaurants and cafes in Bel Air. Savona is one of the most popular restaurants in Bel Air, and it is ranked as the number one restaurant. This Italian delicatessen and wine shop serves a variety of light fare and wine samples.

One Eleven Main is another excellent meal option. They have lovely indoor and outdoor dining areas, as well as a menu full of upscale dishes.

2. Mount Airy

Mount Airy

Mount Airy is a charming town in Maryland that is a culinary and wine lover’s paradise. Both Baltimore and Washington are only 45 minutes apart from this small rural community.

As a result, it’s highly accessible and ideal for a quick weekend getaway. Mount Airy is distinguished by the fact that it is home to some of Maryland’s finest wineries.

In the downtown area, you’ll find the top wineries. Linganore Winecellars and Elk Run Vineyards are two of the most popular wineries. Both offer wine tastings and tours, as well as host fantastic live music events. Make a day of it and take in everything they have to offer.

Linganore has been in operation for almost 45 years and three generations. This cellar frequently holds live music events with meals provided by food trucks. Elk Run Vineyards has a fantastic wine selection to sample.

On Friday, Saturday, and Sunday evenings, they also have live music.

3. Havre de Grace

Havre de Grace

Many people consider Havre de Grace to be one of Maryland’s most beautiful little towns. It is a coastal town with its beauty near the mouth of the Chesapeake Bay.

Guests are invited to stroll along the promenade to the Concord Point Lighthouse. If you’re interested in history, this is a great site to stop for photography. It also includes an outstanding museum.

Havre de Grace is noted for its seafood because it is a seaside town with a river. This small village has some of Maryland’s best seafood.

In the downtown area, there are numerous waterfront eateries and cafés. You can get a true taste of Chesapeake Bay right here.

I especially enjoyed visiting this village and enjoying the half-shell oysters and cooked crabs. Visitors who enjoy seafood will enjoy their visit to this small village.

4. Leonardtown


Leonardtown is next, in keeping with my seafood motif. Beautiful architecture and significant historical buildings may be found in this small town in St. Mary’s County.

Leonardtown also hosts one of Maryland’s most well-known seafood festivals. The National Oyster-Shucking Championship and the US Oyster Festival are held there. Every year, this festival is held in the St. Mary’s County Fairgrounds.

Of course, there’s the actual oyster-shucking tournament to anticipate. But there’s also an oyster cook-off and delectable oysters for sale at the event.

It is one of Maryland’s most popular festivals and a must-see for any seafood enthusiast. Every year, the festival attracts a large crowd, so be sure to attend the next one!

5. Crisfield


I suppose I’ve saved the finest for last on the gastronomic list. Maryland is, of course, known for its seafood. That’s why shellfish is such a popular meal in so many of my favourite culinary towns.

Crisfield, on the other hand, completes this list. Crisfield is known as the “World’s Seafood Capital.” Yes, not only Maryland’s but the world’s seafood capital.

Crisfield is located on the Chesapeake Bay in Somerset County. The name may seem familiar because it is! Crisfield is so well-known for its outstanding seafood that many seafood restaurants around the country now use the name!

When you visit Crisfield, though, you don’t have to eat only wonderful seafood. Festivals provide plenty of entertainment in this town. Every year, Crisfield hosts the National Hard Crab Derby.

The J. Millard Tawes Crab and Clam Bake and the Scorchy Tawes Pro-Am Fishing Tournament are also on the schedule. Both festivities feature a traditional crab and clambake.

If you enjoy seafood, it is something to put on your bucket list.

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Best Maryland Towns for Outdoor Fans

Are you looking for some fun and adventure in the great outdoors? If you are, you will enjoy my list of the top 5 towns to visit in Maryland.

Hiking routes, kayaking, canoeing, sailing, and mountain riding are all available in these towns.

Not to mention the numerous activities available for children. They can even become junior rangers if they want to.

1. Berlin


Berlin is one of Maryland’s most attractive little towns. It boasts a charming Main Street lined with stores, restaurants, and galleries. However, if you like the great outdoors, Berlin has enough to offer.

When I’m on vacation or seeing new cities and towns, I prefer to spend time outside. There is so much to see and do in Berlin that you could easily spend an entire weekend there.

Berlin is home to the Assateague State Park. If you want to, you can stay in the park. There are camping areas and cabins available for rent.

A boat launch, picnic spots, a playground, horseback riding paths, mountain biking, hunting, swimming, and cross-country skiing are all available at the park. For individuals who want to go hiking in Maryland, there are plenty of paths to choose from.

If you want to learn more about the town, they provide fun outdoor concerts that everyone can attend. During the autumn, there is also a well-known peach festival. There will be artisan peach vendors, demonstrations, children’s activities, a pie-eating contest, and more at this event!

2. Monkton


Monkton has to be in the top 10 cutest towns in Maryland. Monkton is a secluded retreat that is a haven for outdoor enthusiasts. Monkton is very stunning, and its green farmlands, old houses, and horse farms drew me in.

The Ladew Topiary Gardens will delight hikers. Guests can meander among the flora of these 22-acre gardens.

Although you do not need to be a skilled hiker to enjoy the Ladew Topiary Gardens, there are some spectacular hikes for those who are. Hikers will find the Northern Central Railroad Walk to be a fascinating trail.

It follows the Pennsylvania border, passes through Monkton Station, and has an abandoned railroad.

Gunpowder State Park is also located in Monkton. There are two lovely waterfalls in this park, as well as a few easy hiking paths. I highly recommend going on a lovely, sunny day to see this.

3. Thurmont


Thurmont should be at the top of your list or very close to it if you enjoy the outdoors. The Gateway to the Mountains is the name given to this settlement. It is located in Frederick County, Maryland, in the northern section of the state.

Thurmont is distinct in that not one, but two state parks border it. This means that the town is surrounded by breathtaking scenery and natural beauty.

In Cunningham Falls State Park, you can also observe Maryland’s largest waterfall. Short and easy walks and walking routes link to this waterfall, making it easy to spot.

Thurmont is also only a short drive from Catoctin Mountain Park. It’s a lovely park that includes a section of the Appalachian Mountains. With over 25 miles of hiking paths, this park is perfect for hikers of all abilities.

Picnic spots and a special program for children are also available. Families with children will enjoy this park because it is designed specifically for them.

Junior Rangers are children who can join in the fun. They can keep themselves occupied with special passes and activity books. This is a great weekend activity for the whole family.

4. Easton


Although Easton is more expensive than many of the other towns on this list, it is one of Maryland’s most attractive small towns. In the downtown area, there are numerous art galleries, upscale stores, and exquisite restaurants.

It hasn’t forgotten its cultural roots, either, as magnificently restored buildings help to keep history alive.

In the summer, Easton is the place to be. They conduct many summer concerts outside. Summer nights are spent listening to music and spending time with loved ones as a result of this.

The Chesapeake Views bike loop is also located in Easton. This is a lovely 38.2-mile trek with excellent water views.

Canoeing, kayaking, and sailing are among the watersports available to adventure seekers. The bay is close by, so all that stands between you and the waves is a short vehicle ride.

5. Oakland


Oakland is one of Maryland’s tiniest little towns. It’s in Garrett County and has a long history with railroads. The rebuilt and historic B&O Railroad Station is a great place to visit if you’re interested in history.

If you’re looking for something more adventurous, Oakland has lots to offer. Swallow Falls State Park, located in Oakland, is a hiker’s paradise. One of the most beautiful hikes in the area may be found in the park.

A waterfall may be found on the Canyon Loop Trail, which is 1.5 miles long. Hikers will be surrounded by lovely natural scenery, mountain laurel, and rocky outcrops.

I was especially pleased to see that there is a handicapped-accessible trail that leads to the falls. This implies that this wonderful natural region isn’t just for the physically fit.

It is open and available to everyone, which is incredibly inclusive and commendable.

The park’s trails are rated easy to moderate, so proceed with caution when water flows. Because the rocks might be slippery and the water can be powerful, exercise caution. It won’t do to be harmed when on vacation hiking!

Best Time to Visit the Small Towns in Maryland

Best Time to Visit the Small Towns in Maryland

Late April through June is, in my opinion, the ideal time of year to visit any of Maryland’s little communities. It’s also a good idea to go between late August and October. Maryland has a relatively mild climate, but it does experience four distinct seasons.

Temperatures range from 64°F to 73°F between April and June. It’s the transition between spring and summer. Therefore there’s a chance of rain. However, with the weather warming up in June, most days should be pleasant and cool.

Around July, Maryland is usually the busiest. It is the most popular time of year for travellers; thus, it is extremely congested.

After August, the tourist season begins to fade, and it is then that the best time to visit is. The weather will be cooler, and you’ll be able to enjoy the stunning fall leaves.

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Final Words

Maryland is a lovely state with a rich and varied history. Small Towns In Maryland are a tribute to the state’s history and culture. It’s a great spot to visit if you like the outdoors, nice cuisine and wine, and history.

I had a great time in Maryland and would encourage everyone to visit and see what the tiny communities offer.

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