The Best Small Towns in Maryland to Chill Out In 2024

What's there not to like about the Old Line State? From the picturesque peaks of the Blue Ridge Mountains to the scenic shores of the Chesapeake Bay, Maryland's beautiful landscapes provide the perfect setting for a relaxed retreat on the East Coast. Forget about the chaos in big cities like Baltimore; the small towns in the backcountry invite travelers to unwind amid quintessential Mid-Atlantic charm.

Off the highway and away from developed beach destinations, hidden communities preserve history, art, nature, and heritage with the easy pace of days past. For those seeking to slow down in 2024, discovering the best small towns in Maryland guarantees gentle reprieve. It's also an excellent opportunity to discover well-preserved history, discover a unique culture, and get lost in the great outdoors!

Grantsville

The pristine natural beauty that encircles this secluded Garrett County village presents an excellent setting to let loose and unwind. Grantsville boasts multiple nature spaces that invite residents for isolated moments in the open, reveling in serenity and taking in the scenery. New Germany State Park easily fits the profile, sprawling over 400 acres and bordering the Savage River State Forest. Recreation opportunities abound here, from hiking and camping to fishing. The same applies to Casselman River Bridge State Park, which, apart from its quiet environment, hosts a historic bridge from the 1800s.

Alternatively, tourists can opt for a solemn trip back in time by touring the House of Yoder. This exciting living museum preserves the memory of the Yoder family, who immigrated to America in the 18th century from Switzerland. A series of period artifacts inside offers a unique look into the times.

Cumberland

Spend a relaxing getaway embracing country living in this beautiful community surrounded by the majesty of the Allegheny Mountains. Cumberland has pleasant outdoor scenery, which you can best witness aboard the Western Scenic Maryland Railroad. This laid-back sightseeing tour on a classic locomotive offers front-seat views of the Allegheny Mountains as it winds through the hilly backcountry. But if you want to get closer to the action, consider heading to Constitution Park and harnessing its various recreation amenities, from sports fields and courts to a swimming pool.

There is a lot of heritage to experience in this delightful community. Back in downtown, the Allegany Museum documents Cumberland's curious history. Meanwhile, the Cumberland Theater offers a taste of local culture by staging live performances like plays, musicals, and concerts.

Mount Airy

Mount Airy boasts one of the most stunning country sceneries in Maryland. Sprawling farmlands, vineyards, and park spaces dominate its landscapes, culminating in pleasant greenery at every corner. The setting is ideal for a relaxing retreat, with escapes like Audrey Carroll Audubon Sanctuary allowing visitors to savor Mother Nature's bounty. A glass of locally made wine at Elk Run Winery while taking in panoramas of rolling hills sets you in the mood for a stress-free vacation.

The local brewery scene plays a vital role in drawing tourists who enjoy the taste of craft beer. Enthusiasts can join friendly townsfolk at Liquidity Aleworks to make merry while sampling local favorites. But if you don't have a soft spot for alcohol, a delicious ice cream cone from Rock Hill Orchard & Woodbourne Creamery is the perfect alternative.

Berlin

This Chesapeake Bay gem promises to relieve stress with beachside fun and water-fuelled recreations. Berlin is home to Assateague State Park, which offers a soothing escape to the Atlantic's sandy shores and clear waters. This barrier island offers a secluded space to kick back, relax, and watch the wild horses casually roaming its shores. Meanwhile, strolling through Berlin's historic downtown is a surreal experience that exposes you to treasures like the Calvin B. Taylor House. Constructed in 1832, the antique building transports you into the Victorian era with unique antiques and memorabilia.

If you like quirky and unusual attractions, visit the Mermaid Museum to browse its strange exhibit collection. This downtown landmark displays various oddities, souvenirs, and artifacts, all centered around the mythical sea creature.

Leonardtown

The slow pace of life in this southern Maryland village compels visitors to take it easy and enjoy the perks a quintessential small town offers. Treating yourself to a casual retail therapy session at Shepherd's Old Field Market is an ideal way to kick off the day's activities. The little outlet sells unique gift items and handmade crafts in a friendly town atmosphere. Elsewhere, Leonard Wharf Park comes in handy when you need an outdoor escape, offering landscaped grounds overlooking Breton Bay and opportunities to get on the water by boating or kayaking.

Any curiosity about Leonardtown's past comes into perspective at the oldest building in town, Tudor Hall. This 1700s brick building stuns with its Georgian-style facade, and touring the rustic interior takes you back to the town's formative years. Before leaving, sample tasty local cuisine at The Front Porch, known for trademark dishes like fried shrimp and oysters.

St. Michaels

Many consider St. Michals one of the best towns in Maryland due to its blend of beautiful beach scenery, rich historical heritage, and a delectable dining scene. The town is along the Chesapeake Bay and offers generous access to recreation on the famous waterway. You can take advantage of this by booking a trip with St. Michael Harbor Shuttle to enjoy a relaxed sightseeing tour of various interest points from the water. Notable among these is the Hooper Strait Lighthouse from 1879. The iconic landmark sits in the middle of the bay, hinting at the town's maritime heritage.

However, you will dive deeper into local nautical history by touring the Chesapeake Bay Maritime Museum. The facility is built on an 18-acre campus and houses world-class exhibitions comprehensively explaining various on-the-water experiences. Finally, sampling Chesapeake Bay's unique cuisine is the ideal way to wrap up a tour of St. Michael's, which is possible with a visit to Foxy's Harbor Grille.

Havre De Grace

Havre de Grace is famous for its rural charm and historical treasures, offering all the hallmarks of a chilled-out getaway. The town's lovely outdoors takes you to where the Susquehanna River pours into the Chesapeake Bay. A lazy stroll along the Havre de Grace Promenade presents the perfect vantage point to witness this epic scene while reveling in the cozy atmosphere. Havre de Grace is replete with museums preserving its rich history and culture. The Havre de Grace Maritime Museum documents the town's maritime escapades on the Susquehanna River and Chesapeake Bay.

Meanwhile, the Lock House Museum documents the history of canals and their operation, exhibited inside a 19th-century structure. After soaking in enough history for a day, you can allow the mind to relax with a picnic at Millard Tydings Memorial Park while enjoying a fresh view of the river.

From the natural beauty of craggy mountains and expansive waters to the historic atmosphere of colonial settlements frozen in time, these cozy small towns in Maryland complement its picturesque environments perfectly for resetting in 2024. Wander or sit back to observe the pace of days gone by. Visitors will relax amid charming main streets, mingle with friendly locals, and sample creative culinary and cultural offerings showcasing regional heritage. Each waterfront and countryside community delivers the perfect chill-out destination for escaping everyday stresses and urban congestion.