The charming resort town of Ocean City, Maryland.

8 Small Towns In Maryland To Visit For A Weekend Getaway

Maryland might be one of the smallest states in America, but it is also among the most beautiful. An original United States colony, Little America houses a treasure trove of history. Its location on the East Coast presents some of the best beach scenery you will come across. While there is a plethora of touristy destinations to visit, the small towns bring out the best of this Mid-Atlantic gem. 

From colonial-era villages to picturesque coastal towns, these pint-sized localities provide the ideal experience for a weekend escape. Whether you are looking to uncover Civil War history, partake in sumptuous seafood, encounter unique cultural traditions, or explore diverse natural landscapes, the small towns in Maryland have it all and then some. Are you planning a weekend tour of Maryland? These are some of the coolest small towns to visit!

Ocean City

The charming resort town of Ocean City, Maryland.
The charming resort town of Ocean City, Maryland.

This scenic resort town sits between the gorgeous waters of the Atlantic and the Isle of Wright Bay. With a modest population of about 7,000, it is one of the best beachside getaways in the state. You will realize this while exploring the Ocean City boardwalk, a 1900s promenade stretching 3 miles with stunning ocean views and bustling with hotels, bars, restaurants, and shops, notably Thrasher's French Fries, Fisher's Popcorn, and Dolle's. Along the boardwalk, you will come across the Ocean City Life Saving Station, which presents a look into the area's history. Built in 1891, it houses a collection of artifacts and exhibits on local sea rescues. 

Another excellent stop on the corridor is Ripley's Believe It or Not, a quirky museum that will intrigue you with strange and shocking exhibits, such as the world's tallest man and a shrunken head. If you are vacationing with kids, you can take them to the Jolly Roger Amusement Park for a raft of fun activities featuring a Ferris wheel, roller coasters, miniature golf, waterslides, and zip lines. For your lodging, book a stay at the Hilton Ocean City Oceanfront Suites to wake up to the best views in town. 


Downtown Hagerstown, Maryland. 
Downtown Hagerstown, Maryland. 

Hagerstown, the county seat of Washington County, is a landmark destination steeped in history. There is a treasure trove of history to uncover in the multiple museums dotting the town, including the Hagerstown Roundhouse Museum, for a look into the local railroad history. Elsewhere, the Discovery Station at Hagerstown is a proper fit for kids curious about history, science, and technology. It hosts a collection of hands-on exhibits and schedules educational programs to stimulate the thirst for knowledge in the young generation. 

Hagerstown also features beautiful outdoors for those who want to explore the town. A great example is the Chesapeake & Ohio Canal National Historical Park Office, where you can bike or hike while discovering the region's history. Alternatively, you can head to Hagerstown City Park to enjoy a tranquil setting with calm walking trails, picturesque artificial lakes, and isolated picnic spots. Hagerstown receives an influx of visitors over the weekend, so you can make a reservation at the Hampton Inn Hagerstown in advance to sort out your accommodation needs. 

St. Michael's

Aerial view of shipyard and lighthouse in St. Michaels harbor in Maryland.
Aerial view of shipyard and lighthouse in St. Michaels harbor in Maryland.

Discover the beauty of the Chesapeake Bay in this scenic waterfront location in Talbot County. St. Michael's delights with a historic harbor and fun sea-based activities like sailing. You can get a feel of the area's rich maritime culture and history at the Chesapeake Bay Maritime Museum, which hosts a world-class collection of artifacts, old vessels, and exhibits. A short distance from the museum, you will encounter the Hooper Strait Lighthouse, an iconic city landmark from the 19th century. The lighthouse lit the way for vessels passing through the dangerous waters of the Hooper Strait. 

Meanwhile, Muskrat Park offers an excellent setting to soak in the natural beauty surrounding St. Michael's. Its idyllic waterfront location spoils visitors with panoramic views of the harbor. Also, the serene atmosphere, with a gazebo and picnic tables, makes it a perfect spot to relax and unwind. For food lovers looking to sample the famous Chesapeake Bay cuisine, the Ruse restaurant serves tasty, wholesome meals in a family-friendly setting. Lastly, you can enjoy a nice stay at the Inn at Perry Cabin. 

Tilghman Island

Residential street on Tilghman Island, Maryland.
Residential street on Tilghman Island, Maryland. Image credit: Chris_Doig (talk) via Wikimedia Commons.

If you fancy a laid-back island getaway from the rigors of urban life, it does not get better than Tilghman Island. This idyllic fishing village in the Chesapeake Bay charms first-timers with a serene atmosphere and unmatched hospitality. You can discover the region's maritime heritage at the Tilghman Watermen's Museum, which preserves the local traditions with exhibits exploring the unique way of life of the island's ancestors. The island is also perfectly placed for you to enjoy water-based fun, and the Tilghman Island Marina & Rentals rents Jet Skis, powerboats, or pontoon boats if you want to get on the water. 

Tilghman Island is known for its vibrant seafood culture, so if you are curious about the town's fresh offerings, remember to stop by Characters Bridge Restaurant and enjoy a tasty bowl of crab soup. After a day-long tour through all the top points of interest in this charming village, you can cap off the visit with a stay at Knapp's Narrows Marina & Inn. 

Bel Air

Bynum Run Creek in Bel Air, Maryland.
Bynum Run Creek in Bel Air, Maryland.

Bel Air is one of the best small towns in Maryland for a romantic getaway. It is renowned for its arts and entertainment district, and strolling through its lively downtown exposes you to a mix of charming venues. If you appreciate art, you can step into the Harford Artists Gallery and browse the unique exhibits or attend a workshop to improve your creative knowledge. Alternatively, you can catch a live performance at the historic Bel Air Armory. But there is more to Bel Air than its artistic heritage and the outdoors delight with gorgeous views. 

You will get a sense of this along the 6.25-mile Ma and Pa Trail, which follows the former Ma and Pa Railroad. The relatively easy route is perfect for a lazy afternoon walk or jog with family. For history buffs, the Liriodendron Mansion is a historic home and former abode of Dr. Howard Kelly worth a tour. Its beautiful façade provides the perfect background for a photo. Finally, you can find affordable yet quality accommodation at the quaint Quality Inn & Suites while in Bel Air. 


The Swallow Falls State Park in Oakland, Maryland.
The Swallow Falls State Park in Oakland, Maryland.

Oakland presents an excellent escape for nature lovers and outdoor enthusiasts. This tiny town in Garrett County boasts multiple venues where you can go to be one with nature. At Swallow Falls State Park, you will find scenic natural trails that pass through old-growth forests leading to the magnificent Muddy Creek Falls. The magnificent park is a recreational hub that also houses over 65 campsites, picnic areas, biking paths, and beautiful overlooks. You can have the same kind of fun at the Herrington Manor State Park, which sits adjacent to the Swallow Falls State Park and hosts a 53-acre beach ideal for swimming and fishing. 

The town is also home to the Oakland B & O Railroad Museum, a venue showcasing Oakland's railroad heritage through historical artifacts and exhibits. Also, you will get a wider perspective of the area's history at the Garrett County Historical Museum, which harbors a wide collection of memorabilia that takes you through the ancient eras. When you have been to all the main attractions, you can enjoy a good night's sleep at the simple yet classy Oakland Motel. 


The visitor center for Catoctin Mountain Park in Thurmont, Maryland.
The visitor center for Catoctin Mountain Park in Thurmont, Maryland. Editorial credit: Liz Albro Photography /

Thurmont's motto, "The Gateway to the Mountains," portrays a picture of the stunning natural landscapes surrounding the town. This tiny community of less than 7,000 lies at the foothills of the Catoctin Mountains, providing adventurers with endless outdoor opportunities. At Catoctin Mountain Park, you can choose from 25 miles of hiking trails, ranging from easy to difficult, to explore the wild backcountry. The site is also ideal for camping, fishing, and cross-country skiing, with stunning vistas of the region. More recreation activities await at the Cunningham Falls State Park, which offers a more family-friendly setting, with the highlight being the largest waterfall in Maryland, Cunningham Falls. 

If you are an animal lover, Catoctin Wildlife Preserve provides an excellent opportunity to interact with amazing species. The 100-acre zoo houses animals like bears, macaws, zebras, and panthers. It has a petting zone where you can get up and close with the animals and show some TLC. Although there are several B&Bs to spend the night in, the Ole Mink Farm Recreation Resort provides many lodging options, from lodges and cottages to cabins. 


Pumpkins growing in a field near Leonardtown, Maryland.
Pumpkins growing in a field near Leonardtown, Maryland.

Leonardtown is a mixed bag of delights, with a little bit of something for everyone. This tiny town in St. Mary's County hosts less than 5,000 residents and draws visitors with unique history, beautiful architecture, and culture-rich festivals. You can explore some of its historical landmarks at Tudor Hall, a Georgian-style house built in the 1700s. Another interesting spot to check out is Moll Dyer Rock, where Moll Dyer, accused of practicing witchcraft and driven out of her house, was found frozen. The rock is rumored to still bear Dyer's handprint. 

If you are more inclined to the outdoors, you will find the perfect environment at Leonardtown Wharf Park. The venue is a popular meeting point for the community and hosts various recreational activities, including kayaking, picnicking, and paddle boarding. Finally, do not forget to pop into The Front Porch restaurant for some Southern Coastal delicacies before spending the night at the Inn at Leonardtown. 

The Takeaway

When planning a Maryland itinerary, you can easily get overwhelmed by the sheer number of options. Unlike famous big cities like Baltimore, the small towns in Maryland showcase the true heart and soul of the state, delivering experiences that you would not find anywhere else. From unique historical landmarks and rich cultural attractions to wild outdoor adventures, they have all the ingredients for a remarkable weekend getaway.

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