Exploring Maryland’s Charming Small Towns
Maryland is full of small towns that are simply begging to be explored. During my recent trip, I discovered several hidden gems that beautifully showcase the state’s charm and character.
Renowned for its seafood and watersports, Maryland’s coastal location makes it a haven for fresh catches and boating adventures. The largest city, Baltimore, has long been a major seaport, adding a rich maritime history to the region that resonates in both the culture and cuisine of the surrounding towns.
Whether you’re looking for history, nature, or simply a relaxing getaway, Maryland’s small towns offer a perfect mix of experiences.
If you like, I can expand this into a full guide of must-visit small towns in Maryland with what to do, eat, and see in each. Do you want me to do that?
However, for this article, I’ll be focusing on Maryland’s small towns. With so many wonderful options, narrowing it down to just fifteen was quite a challenge! I highly recommend putting Maryland on your travel list and exploring everything this charming state has to offer.
To make planning easier, I’ve split the towns into three categories:
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Historic small towns – perfect for history lovers.
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Towns for foodies – where local flavors shine.
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Towns for outdoor enthusiasts – ideal for hiking and other activities.
15 Best Small Towns in Maryland
Each town on this list is unique, offering something special whether it’s history, food, or outdoor adventures. I’ll also highlight the best time of year to visit each destination.
Maryland’s Most Historic Towns
Choosing historic towns was tough because there are so many gems. After careful consideration, I narrowed it down to five towns that offer a mix of activities for all ages: from kid-friendly attractions, museums, and historic railways, to uncovering fascinating local stories that bring Maryland’s past to life.
1. St. Mary’s City
There are a number of historic towns in Maryland. However, St. Mary’s City is a historic town and known as Maryland’s first European capital and settlement.
It is also the fourth-oldest permanent English settlement in the United States. History fans flock to St. Mary’s City to be able to experience the history of the area firsthand.
This is one of the very best historic towns in America. It has information on history, archeology, and tells the extraordinary tale of Maryland’s first-ever capital. It is possibly the smallest town in Maryland that has a commercial aspect, with a population of less than 1000.
This little town makes history fun and interactive. It is, therefore, a terrific place for children to learn about heritage and history.
There are living history museums where the staff will be dressed up in period costumes. They will also recreate actual historical events.
If you do choose to visit St. Mary’s City, I highly suggest going to visit the restored original colonial settlement. It is a must-see for anyone interested in history and culture.
I also suggest popping into the local, working colonial farm and going to see the Dove Sailing Ship. This is a working replica of one of the two original settler ships of the very first Maryland Colony.
2. New Market
This small town in Maryland is located just 50 minutes from Baltimore. It is known as the Antiques Capital of Maryland, which makes it historically significant.
There are so many unique shops here that you do need a weekend to explore them all. I myself spent a good few hours just on Main Street. There are numerous antique shops as well as restaurants and cafés to keep you busy.
Families will rejoice in the Original Playhouse. This building on Main Street is a children’s museum that will keep the little ones busy for hours.
This museum has interactive games for children and the games work with imagination rather than batteries. The museum aims to use play to develop children’s emotional intelligence and reasoning skills.
The best time to visit New Market would be in either December or May. There are two very well-known festivals that are held every year in these two months.
These festivals aim to highlight and recreate what life was like in the 18th and 19th centuries. The festivals are known as Christmas in New Market, in December, and A Day in New Market, in May.
3. Ellicott City
This little town is a haven for train enthusiasts, and it is the home of the country’s oldest existing railway station. It is well-known as one of the more historic sites in Maryland, and travelers frequently stop here.
I have a particular fondness for historic architecture. The Main Street in Ellicott City is dotted with approximately 200 buildings from the 18th and 19th centuries. I spent hours just walking by and being mesmerized by the beauty of the ancient buildings and homes.
Ellicott City also houses the Patapsco Female Institute. This revolutionary institution educated young women between 1837 and 1891. It was one of the first schools to offer subjects like chemistry and mathematics to female pupils. You can visit the restored site for a history tour on weekends.
The Historic Savage Mill is an old cotton mill. It has been renovated and now houses a variety of galleries and restaurants. Ellicott City also boasts several modern boutiques and shops, so there is something to keep everyone happy on the trip.
4. Pocomoke City
This is one of the small towns in Maryland that is located in the south. It is just north of the border to Virginia. The city gets its name from the Pocomoke River that runs through its downtown area.
The historic town is well-known for its documentation of the early Maryland colonies, therefore it is a favorite among history buffs.
The Delmarva Discovery Centre is a museum and one of the most popular attractions in town. The museum houses fascinating exhibits in the natural surroundings of the Delmarva peninsula. It also explores the history of the original colonies of this area.
The history exhibits feature information and scenes of the Delmarva natives. There are also artifacts to peruse. The exhibits on habitats explore species native to Delmarva. At these exhibits, guests can get up close and personal with the animals, which is very exciting.
You can also steer a steamboat, walk into a wigwam, and take a peek into a beaver’s dam. This is truly a museum that caters to every taste!
5. St. Michael’s
St. Michaels is a beautiful little town on the eastern shore in Maryland. It used to be a bustling seaport, but now people tend to spend their weekends relaxing by the water.
The current population is just over 1000, but during the peak season, it gets quite busy. If you like seaside towns and nautical history, this is the place for you.
St. Michaels is located in the Chesapeake. That means that it has a very impressive history regarding being a stop for sailors. The Chesapeake Bay Maritime Museum is located here and boasts a waterfront of 18 acres, beautiful exhibitions both indoors and outdoors, and a gorgeous marina.
You will also get to see some historic vessels when you visit this National Historic Landmark.
St. Michaels is also home to the famous Talbot Street. Talbot Street is known for its local wineries. There you can wind down after a day exploring the nautical history of the area. Or hop on a harbor cruise and explore the bay!
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Best Places To Visit For Food and Drinks
If you are a food lover like myself you will never find a shortage of fine food and drinks in these small towns.
I’m going to list 5 places you must visit starting with Bel Air. You will be spoiled for choice with endless amounts of restaurants, breweries to visit, a selection of craft drinks, and fine wine to taste.
1. Bel Air
Bel Air is one of the larger towns in Maryland, and it is what I would call foodie heaven. If you, like me, are a foodie, then you enjoy fine foods, good wine, and a selection of craft drinks. Bel Air has a large selection of excellent craft breweries.
The Independent Brewing Company is on the Main Street of Bel Air. It is one of the top breweries in Harford County. It has a very large taproom and patio where you can enjoy their brews.
They always have 26 ciders and ales on offer, and these rotate by season. Therefore, you’re always likely to find something new.
Bel Air also has no less than 57 restaurants and eateries. Savona is one of the top choices for restaurants and is listed as the number one restaurant in Bel Air. This Italian Delicatessen and Wine Shop offers a wide range of light meals as well as wine tastings.
One Eleven Main is another restaurant that is a top choice for dinner. They have beautiful indoor and outdoor dining options and a menu filled with upmarket dishes.
2. Mount Airy
Mount Airy is one of the cute towns in Maryland that offers a haven for food and wine lovers. This rural town is just 45 minutes drive from both Baltimore and Washington.
This makes it very accessible and perfect for a short weekend getaway. What makes Mount Airy so unique is that some of the best wineries in Maryland are located right here.
The best wineries are located in the downtown area. Two of the most popular wineries are Linganore Winecellars and Elk Run Vineyards. You can do wine tastings and tours at both of these and they host wonderful live music events. So, make a day of it and explore all they have to offer.
Linganore has been in business for three generations and more than 45 years. This cellar often hosts live music events where they have food trucks to provide catering. Elk Run Vineyards have a wonderful selection of wines to taste.
They also host live music on Friday, Saturday, and Sunday evenings.
3. Havre de Grace
Many people believe that Havre de Grace is one of the most beautiful small towns in Maryland. It is a coastal town and it has a certain charm of its own at the top of Chesapeake Bay.
The promenade invites guests to meander to the Concord Point Lighthouse. This is the ideal place to stop for photos and also has an impressive museum if you’re interested in history.
Due to the fact that Havre de Grace is a coastal town and located by a river, it is known for its seafood. This little town boasts some of the best seafood in Maryland.
There are many waterfront restaurants as well as cafés in the downtown area. Here you can sample the true flavor of Chesapeake Bay.
I particularly enjoyed visiting this town and sampling the oysters on the half shell as well as steamed crabs. Seafood lovers won’t regret paying this little town a visit.
4. Leonardtown
In keeping with my seafood theme, Leonardtown is next. This little town is situated in St. Mary’s County and it has beautiful architecture and fascinating historical sites.
Leonardtown also hosts one of the most prominent seafood festivals in Maryland. It is the home of the National Oyster-shucking Championship and US Oyster Festival. The St. Mary’s County Fairgrounds hosts this festival every year.
There is, of course, the actual oyster-shucking competition to look forward to. But the festival also hosts the oyster cook-off and delicious oysters for sale.
It is one of the top festivals in Maryland and a must-see for any seafood lover. The festival draws an enormous crowd every year, so make sure you catch the next one!
5. Crisfield
On the foodie list, I do believe I’ve saved the best for last. Of course, Maryland is synonymous with seafood. That is why so many of my foodie-favorite towns feature seafood as the prominent cuisine.
However, I round out this list with Crisfield. Crisfield is known as the Seafood Capital of the World. Yes, not only the seafood capital of Maryland but of the world.
Crisfield is situated in Somerset County in the Chesapeake Bay. If the name sounds familiar, it might be because it is! Crisfield is so well-known for excellent seafood that many seafood restaurants in other parts of the country carry the name!
However, you don’t just have to dine on delicious seafood when you pop in to visit Crisfield. Entertainment in the form of festivals is abundant in this town. The National Hard Crab Derby takes place in Crisfield every year.
Also on the calendar are the J. Millard Tawes Crab and Clam Bake, and the Scorchy Tawes Pro-Am Fishing Tournament. Both of these events showcase a real crab and clambake.
It is definitely something to jot down on your bucket list if you love seafood.
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Best Maryland Towns for Outdoor Enthusiasts
Are you looking for some outdoor adventure and fun? If you are then you will love my list of top 5 places you must visit when in Maryland. These towns have hiking trails, kayaking, canoeing, sailing, and mountain biking tracks.
Not to mention there is an abundance of things to do for children. They can even participate and become junior rangers.
1. Berlin
Berlin is one of the most beautiful small towns in Maryland. It has a picture-perfect Main Street filled with adorable shops, restaurants, and galleries. But if you’re more of the outdoorsy type, Berlin has plenty in store for you too.
I tend to enjoy spending time outdoors when on vacation or exploring new cities and towns. Berlin has so much to do that you can easily spend an entire weekend there.
The Assateague State Park is located in Berlin. You can actually stay in the park if you’d like. There are camping facilities and cabins that you can rent.
The Park also offers a boat launch, picnic areas, a playground, horseback riding trails, mountain biking, hunting, swimming, and cross-country skiing. There is also an abundance of hiking trails for those that would like to go hiking in Maryland.
If you’d like to explore the town itself a little more, they do fun outdoor concerts that anyone can attend. There is also a famous peach festival that takes place during the fall. This festival includes artisan peach vendors, demos, kids’ activities, a pie-eating contest, and more!
2. Monkton
Of all the cute towns in Maryland, Monkton has to be in the top ten. Monkton is a rural escape and is an absolute paradise for outdoor enthusiasts. Monkton is absolutely beautiful and captivated me with its lush farmlands, historic houses, and horse farms.
Hikers will rejoice in the Ladew Topiary Gardens. These gardens span 22 acres and guests can meander through the foliage.
Although you do not need to be an experienced hiker to walk in the Ladew Topiary Gardens, there are some exquisite hikes for the more experienced hiker. The Northern Central Railroad Trail is a very interesting trail that will fascinate and excite hikers.
It follows the Pennsylvania border, features an abandoned railroad, and even takes you right through Monkton Station.
Monkton also houses the Gunpowder State Park. This park features a few easy hiking trails and two beautiful waterfalls. I highly suggest checking this out on a nice, sunny day.
3. Thurmont
If you love the outdoors, then Thurmont should be either at the top or very near the top of your list. This town is known as the Gateway to the Mountains. It is in Frederick County in the northern part of Maryland.
What makes Thurmont so unique is that it borders not one but two state parks. This means that the town is surrounded by natural beauty and awe-inspiring sights.
The largest waterfall in Maryland can also be seen here in the Cunningham Falls State Park. It is easy to find this waterfall with short and easy hikes and walking trails leading to it.
The Catoctin Mountain Park is also just a very short distance from Thurmont. It is a beautiful park that features a part of the Appalachian Mountains. This park has over 25 miles of hiking trails, so is absolutely ideal for hikers of all skill levels.
There are also picnic areas and an entire program just for kids. Families with children will delight in this park as they are very much focused on the little ones.
Children can join in the fun by becoming Junior Rangers. There are special passes and activity books to keep them busy. This is the ideal family-friendly weekend activity.
4. Easton
Easton is a little more upscale than many of the other towns on this list, but it is still one of the most beautiful small towns in Maryland. There is an abundance of art galleries, upmarket boutiques, and lovely restaurants in the downtown area.
However, it has not lost its cultural roots and keeps history alive with beautifully restored buildings.
Easton is the place to be in summer. They host a variety of outdoor summer concerts. This means summer nights are spent listening to music and spending time with loved ones.
Easton is also situated right by the Chesapeake Views bike loop. This is a beautiful 38.2-mile trail with stunning views of the water.
Adventure lovers can head to the waters to partake in canoeing, kayaking, or sailing. The bay is very close by, so only a short car ride stands between you and the waves.
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5. Oakland
Oakland is one of the tiniest small towns in Maryland. It is located in Garrett County and has a rich railroad history. If you’re interested in history, you can explore the restored and historic B&O Railroad Station.
However, if you’re more of the adventurous type, Oakland has plenty to offer as well. The Swallow Falls State Park is in Oakland and it is a haven for hikers. The park is home to one of the most scenic hikes in the area.
The Canyon Loop Trail is 1.5 miles long and features a waterfall. Hikers will see beautiful natural surroundings, mountain laurel, and rocky outcrops.
I was particularly happy to discover that there is a handicap-accessible trail available that also leads to the falls. This means that this beautiful natural area isn’t only accessible to able-bodied persons.
It is open and accessible to all, which is very inclusive, and something to be commended.
The trails in the park are marked as easy to moderate, so use caution where water flows. Rocks can be slippery and the current can be very strong, so just be careful. It won’t do to get hurt on your hiking holiday!
Best Time to Visit the Small Towns in Maryland
Best Time to Visit Maryland’s Small Towns
The ideal time to explore Maryland’s charming small towns is late April through June or late August through October. Maryland enjoys a fairly temperate climate with four distinct seasons, making spring and fall especially pleasant for visitors.
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Late April to June: Temperatures range from 64°F to 73°F. Days are generally cool and comfortable, warming up as summer approaches. Some rain is possible, but the scenery is lush and green.
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Late August to October: After the busy summer tourist season, the crowds thin out, and the weather is more comfortable. Fall foliage paints the towns with stunning colors, making it a photographer’s dream.
Avoid July if you dislike crowds, as this is the peak tourist season and towns can feel quite busy.
Why Visit Maryland’s Small Towns?
Maryland’s small towns are full of history, culture, and natural beauty. They are perfect for those who enjoy:
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Outdoor adventures and scenic walks
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Local cuisine and wine tasting
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Exploring historical sites and charming streets
My Takeaway: Maryland is a wonderful destination for a relaxing and enriching trip. Its small towns showcase the state’s rich history and vibrant culture. I highly recommend exploring them, whether you’re a history enthusiast, foodie, or nature lover.