15 Best Small Towns to Visit in Maryland

Written by Jan Meeuwesen
Updated on
Our travel recommendations are based on our personal experiences and research, written by locals and travel experts with deep familiarity with the destination. When you book a hotel or tour that we link to, we may earn a commission.

Maryland, one of the original thirteen colonies, is a Mid-Atlantic state with beautiful coastlines along the Chesapeake Bay and Atlantic Ocean. With small towns located both along the seaside and the sprawling countryside, Maryland is steeped in colonial history just waiting to be explored.

Take some time away from Baltimore and the major city attractions and experience small-town Maryland – sometimes you’ll even feel like you’ve gone back in time and are experiencing US History in person! You’ll both learn and have fun at the same time while you sample the good food and drink that these towns have to offer, or jet off into the sunset on an exciting boat tour.

Check out our recommendations for the best small towns to visit in Maryland:

1. Thurmont, Maryland

Thurmont, MarylandSource: flickr
Thurmont, Maryland

A small town in Frederick County, Thurmont is in the northern part of Maryland and quite close to the Pennsylvania border. A designated “Main Street Maryland Community” the town worked to preserve its historic downtown while retaining charm and proximity to nature – its motto is “The Gateway to the Mountains”. Come visit if you’re an outdoors enthusiast or art lover!

Thurmont hosts Catoctin Colorfest each year, an arts festival that attracts up to 125,000 people. Even if you don’t make it, visit just to see Cunningham Falls State Park and Catoctin Mountain Park (where Camp David is located). Bring your hiking boots and hit the trails here, or take it easy and settle for a stroll across Loy’s Station Covered Bridge. You can also get your hands on fresh fruit at Catoctin Mountain Orchard or go wine tasting at Springfield Manor Winery and Distillery.

2. Berlin, Maryland

Berlin, MarylandSource: marlincoveoc
Berlin, Maryland

No, we’re not talking about the capital of Germany. Berlin, Maryland is located in Worcester County. The name isn’t even derived from German – the locals say that it is a variation of the name of an old tavern, Burleigh Inn, that used to be located in town. A popular destination for tourists in search of fishing and hunting grounds, Berlin has recently revitalized the downtown area to be recognized as a Maryland Mainstreet Community.

Check out nearby Assateague State Park or head to Dr. Shred’s Surf Adventures if you’d spend time at the beach. Bring your camera and wander Main Street’s historic buildings and shops before stopping in for a pint at Burley Oak Brewing Company or a glass of wine at Maryland Wine Bar. The Blacksmith serves up some great food, and you can stop in for dessert at Bakes Dessert Cafe after. Put your feet up at Holland House Bed and Breakfast and enjoy a peaceful night’s sleep!

3. Hampstead, Maryland

Hampstead, MarylandSource: wikipedia
Hampstead, Maryland

Located in Carroll County, Hampstead was founded when Robert Owings started building a new road through the state. It was first called Spring Garden before changing its name to Hampstead. Originally settled by the English, the town was an agricultural hub due to its fertile lands. Now though, the sleepy farming community has awakened to find itself a modern town and awaits your visit.

When you’re here, why not go riding at Happy on Hooves? If you prefer to stand on your own feet, check out Prettyboy Reservoir Park or Leister Park. You can drive out to Cascade Lake and go swimming, too. Try the local eats at A Town Bar and Grille or something sweet at Snickerdoodles Bakery and Coffee house. Hilltop Hideaway Bed and Breakfast is on standby for you when you decide you need a rest.

4. Crisfield, Maryland

Crisfield, MarylandSource: flickr
Crisfield, Maryland

Crisfield, a town in Somerset County, is located on the Tangier Sound on the Chesapeake Bay. Originally a small fishing village, it was renamed Somers Cove before John Crisfield decided to cash in on exporting seafood and brought the Pennsylvania Railroad to town. Thus, the town was re-christened Crisfield and is now known as the “Seafood Capital of the World” (Locals claim that downtown is literally build on oyster shells!).

While business has diminished with the decline of Chesapeake Bay, the town kept busy by bringing in tourism and hosting festivals, such as the National Hard Crab Derby. It’s also a great access point for Smith Island and Tangier Island – rent a boat and head out to explore! Visit to see an authentic crab and clambake at the J. Millard Tawes Crab and Clam Bake, or the Scorchy Tawes Pro-Am Fishing Tournament. You should also spend some time exploring the marshes at Janes Island State Park, an undeveloped island full of marine and bird life.

5. Eastport, Maryland

Eastport, MarylandSource: flickr
Eastport, Maryland

A perfect alternative to the city bustle, Eastport is right across the bridge from Annapolis. Located on a lovely peninsula, Eastport offers that laid-back atmosphere small towns are known for. With views of Annapolis’ best landmarks – the State House and Naval Academy – you can enjoy the waterfront views that the town has to offer and the proximity to a big city while maintaining a relaxed vibe.

Eat at any one of the dining spots along the water; we recommend Carrol’s Creek Cafe. If you’re a watersports enthusiast, rent a kayak at Third and Severn and head out for a day on the water. Or, stay on land and go to the Maritime Museum. Sometimes Eastport hosts outdoor concerts and oyster festivals, or pirate ship adventures on the water! Eat a crab pretzel from Davis’ Pub and enjoy the fresh air.

6. Ocean City, Maryland

Ocean City, MarylandSource: flickr
Ocean City, Maryland

A resort destination in Worcester County, Ocean City is a popular destination for tourists from the Mid-Atlantic region. Population swells during the summer as people descend to the coast for a coastal getaway. The land on which the town stands was originally owned by Thomas Fenwick, an English immigrant, and was developed in the late 1800s Isaac Coffin because to develop the town to attract tourists. He must have done a good job, because they’re still coming!

Treat yourself to a luxury vacation here. The Princess Royale Resort awaits your visit, and boasts prime waterfront views sure to impress you. Enjoy dinner with a view at the Hobbit Restaurant or Shark on the Harbor before going for drinks at Harborside Bar. Bring your swimsuit and head down to Ocean City Beach and Boardwalk for some fun in the sun or rent a boat at Odyssea Watersports!

7. Havre de Grace, Maryland

Havre de Grace, MarylandSource: flickr
Havre de Grace, Maryland

Located the Susquehanna River, Havre de Grace sits where the river meets Chesapeake Bay. Named after a town in France (Le Havre de Grace), the town was renamed this during the Revolutionary War, following several visits by Lafayette, who said that the town reminded him of the French seaport, Le Havre.

Come visit this lovely seaside town to understand what enchanted Lafayette so much. Stay at the Spencer-Silver Mansion, and book the carriage house if you get a chance! Take a lovely walk along the waterside at Havre de Grace Promenade, or walk down to the Concord Point Lighthouse. Explore the trails at Susquehanna State Park or play a round of golf at Bulle Rock Golf Club. Top off the weekend with a glass (or two!) at Mount Felix Vineyard & Winery.

8. Monkton, Maryland

Ladew Gardens, Monkton, MarylandSource: flickr
Ladew Gardens, Monkton, Maryland

A true country getaway, Monkton is located in Baltimore County. A haven for those in need of a rural vacation, the area around this community is filled with sprawling countryside, horse farms, and historic old homes. Stop by if you’re driving through, you’ll find it to be one of Maryland’s hidden gems.

Come visit if you’re a horse lover – if you go a bit east, you’ll hit “My Lady’s Manor”, several acres of land known for their horse farms. Check out Ladew Topiary Gardens as well or stop in for a drink at Millstone Cellars. The bison burgers at Gunpowder Bison & Trading Co are sure to impress, and is a perfect break if you’ve been driving for awhile and need to stretch your legs.

9. Oakland, Maryland

Oakland, MarylandSource: flickr
Oakland, Maryland

A town in the west-central part of Garrett County, Oakland is a former railroad town, it is still home to a historic and preserved B&O railroad station, and trains still run on the tracks through the station for special occasions!

Come visit and check out the Oakland B&O station yourself if you’re a train buff, or bring your walking shoes and head out to Swallow Falls State Park. Go horseback riding at Circle R Ranch, or play a round of golf at Lodestone Golf Club. You can head out on the water with a boat rental from Brill’s Marine Service, and put your feet up after at the Will O’ the Wisp hotel. A perfect getaway with nature, you’ll find yourself wanting to stay a little longer.

10. St Mary’s City, Maryland

St Mary’s City, MarylandSource: flickr
St Mary’s City, Maryland

A former colonial town, St Mary’s City was the first colonial settlement in Maryland. The town is the site of where the Colony of Maryland was founded, making it the fourth oldest permanent English settlement in the US! St. Mary’s City was also the first place in the US that specifically created a refuge for both Catholics and Protestants. A perfect vacation for the history buff, you’ll see and experience history hands-on here!

You can see the visit the reconstructed original colonial settlement, as well as explore any of the living history museums open to the public – the staff are dressed in period clothing and recreate historical events! You can visit a working colonial farm and the functioning replica of The Dove Sailing Ship (one of two original settlers’ ships that founded the Maryland Colony). Learning history has never been so fun!

11. New Market, Maryland

New Market, MarylandSource: flickr
New Market, Maryland

New Market is located in Frederick County, and is known as the “Antiques Capital of Maryland”. Founded when trade routes between Frederick and Baltimore were established, the town quickly asserted itself as an important stop along these routes, and remains a popular destination to this day.

Explore the downtown area and wander the small shops that specialize in the sale of antiques and other assorted goods. New Market even holds two annual festivals to highlight their past: “Christmas in New Market” in December, and “A Day in New Market” in May, to commemorate traditional 18th and 19th century life. Whether you make it to the festivals or not, stop in for a meal at Vintage or for a night at Strawberry Inn B&B.

12. Vienna, Maryland

Vienna, MarylandSource: flickr
Vienna, Maryland

Located in Dorchester County, Vienna was surprisingly not founded by Austrians as one might believe, but was actually first visited by the English when Captain John Smith encountered the Nanticoke Indians during his explorations. It is conveniently located on the Nanticoke River and is surrounded by lush greenery.

If you’re not busy exploring the riverbank or taking a canoe out, stop by Layton’s Chance Vineyard and Winery for a few glasses of delicious wine. Stay a few nights at the peaceful Tavern House, located right on the water and offering spectacular views. Watch the sunset at the River Pavilion or along the Waterfront South and disconnect from the hustle of city life.

13. Emmitsburg, Maryland

Emmitsburg, MarylandSource: flickr
Emmitsburg, Maryland

Emmitsburg is located in Frederick County, a bit south of the Mason-Dixon Line that separates Maryland from Pennsylvania. A pilgrimage site for Catholics, the town is home to both the National Shrine Grotto of Our Lady of Lourdes, and the Basilica and National Shrine of St. Elizabeth Ann Seton (the first natural born US citizen to be canonized as a saint). Whether you are Catholic or not, the town boasts panoramic views of lush countryside and historic buildings worth visiting.

Visit the Mason Dixon Welcome Center while you’re here, or the historic Mount St. Mary’s University. Head out to the pilgrimage sites, or go to the Emmitsburg Antique Mall instead. The Ott House Pub is perfect for a drink on a lazy afternoon before dinner at the Carriage House Inn. You can stay the night here for a peaceful night’s sleep too if you’re so inclined.

14. Leonardtown, Maryland

Leonardtown, MarylandSource: flickr
Leonardtown, Maryland

Leonardtown is the county seat of St. Mary’s County, and a mecca for seafood lovers. Recently, the town has started revitalizing their downtown area and opening up new businesses in historic buildings, and opening the Leonardtown Wharf. Pay Leonardtown a visit to go shopping or if you’re into watersports.

Go shopping at the Wharf or walk along the waterfront to enjoy the views. You can rent boats, kayaks or canoes if you’d like, or continue exploring the historic downtown area. Check out Tudor Hall or St. Andrew’s Church, two buildings listed on the National Register of Historic Places before treating yourself to a pint or two at Fitzies Marina Restaurant and Pub. You can always stay a few nights at the Executive Inn.

15. St. Michaels, Maryland

St. Michaels, MarylandSource: flickr
St. Michaels, Maryland

A town in Talbot County, the town is named after the Episcopal Parish established there in 1677 well before the town was established in the 1700s. St. Michaels grew as settlers flocked to town to start business, build ships, or grow tobacco. It was also the grounds of a battle between the British and the Americans in the War of 1821, when it was targeted by the British because of a militia battery. According to local legend, the town was spared destruction from the cannonballs of the British by hanging lanterns out in the trees beyond the town, and thus becoming known as the town that “fooled the British”.

If you visit now, you can still see the Cannonball House, a surviving structure that was reportedly hit by a cannonball. Wander the center of town and see their Historic District, or visit the Episcopal Church off the main road. Spend some time at the Chesapeake Bay Maritime Museum to learn about the unique boats developed by the town, or have fresh seafood at St. Michaels Crab & Steak House. You’ll be charmed by this lovely seaside town and want linger a bit longer.

15 Best Small Towns to Visit in Maryland:

  • Thurmont, Maryland
  • Berlin, Maryland
  • Hampstead, Maryland
  • Crisfield, Maryland
  • Eastport, Maryland
  • Ocean City, Maryland
  • Havre de Grace, Maryland
  • Monkton, Maryland
  • Oakland, Maryland
  • St Mary’s City, Maryland
  • New Market, Maryland
  • Vienna, Maryland
  • Emmitsburg, Maryland
  • Leonardtown, Maryland
  • St. Michaels, Maryland