13 Nicest Small Towns In Maryland
Millions of tourists travel to Maryland every year to experience its enduring colonial history, taste its famous blue crab dishes, and explore its wonderful natural landscapes. Between the Appalachian Mountain range to the west and the Chesapeake Bay to the east, the Old Line State has no deficiency of charming destinations worth visiting. Although many people choose to visit major cities like Baltimore, the state's authentic character stays hidden in the backcountry across its rural communities.
From quaint little towns with vibrant Main Streets to shoreline villages teeming with maritime heritage, these precious gems connect travelers with the splendor of Maryland's countryside. Whether you plan to chill by the beach in Ocean City or hike through the mountains in Thurmont, these beautiful small towns in Maryland treat vacationers to an unforgettable retreat.
Saint Michaels
Small, serene, and scenic, Saint Michaels is a lovely vacation getaway on the shores of Chesapeake Bay, known for its comfortably warm weather, wonderful waterfront, and seafood dishes. Guests can expect to let loose during nonchalant trips on the calm sea waters, courtesy of Patriot Cruises. This culminates in a remarkable sightseeing adventure showcasing the town's beauty, enduring history, and majestic wildlife species.
St. Michael's is steeped in Maritime heritage and preserves its dynamic past at the 18-acre campus of the Chesapeake Bay Maritime Museum. Here, you can examine interactive exhibits like old boats, defunct vessels, and related artifacts for an interesting journey through time. You can't leave Saint Michaels without trying out its celebrated seafood dishes, featuring trademark crab dishes, alongside fresh craft beer at the riverfront Foxy's Harbor Grille.
Chesapeake City
Chesapeake City's charm lies in its soothing small-town environment and unmatched ocean views. Thanks to its setting along the Chesapeake Bay shoreline, opportunities abound to get on the water for an alternative perspective of the town's natural beauty. This is possible through the Chesapeake Water Tours, which take guests on premier boat cruises curated to their preferences, from sunset cruises to craft beer tours. At Pell Gardens Park, tourists can revel in the community's laid-back atmosphere while relaxing in a delightful outdoor oasis overlooking the water. The sweet-scented sea breeze works with lush greenery around the park to grant you an easygoing time outside.
The Chesapeake City Historic District preserves the city's colorful historical heritage. The Chesapeake City Museum, among a collection of 19th—and 20th-century structures, offers a chance to learn about the town's chronology.
Berlin
A sought-after escape on Maryland's Eastern Shore, Berlin is famous for its vibrant downtown district and preserved historical gems. A tour of the tree-lined streets of the historical Berlin Commercial District allows you to witness how the new mixes with the old. Several buildings in the area, including the Calvin B. Taylor House, provide a vivid glimpse of the past. Built in 1832, the Federal-style home retains its original period furnishings and offers an idea of life in the Victorian era.
There are over 50 restaurants, gift shops, and boutiques along Berlin's ever-busy Main Street. If you want to hang out and meet locals, you can do so with a craft beer session at the lively Burley Oak Taproom & Brewing Company. Beyond the downtown, outdoor lovers respond to the call of nature by visiting Assateague State Park. This isolated barrier island is known for its adorable Atlantic beaches, winding trails, and thriving wildlife, including bald eagles, seabirds, and wild Chincoteague ponies.
Boonsboro
This Washington County community, set on the foothills of South Mountain, lures travelers with its pristine natural beauty and remarkable outdoor adventures. Boonsboro harbors Greenbrier State Park, a popular hub for a variety of recreational activities. The reserve features a 42-acre reservoir and supports fishing, boating, picnicking, swimming, and canoeing. South Mountain State Park invites adventurous hiking expeditions on the rugged terrain of the famous Appalachian Trail. The route promises spectacular overlooks, such as High Rock and Weverton Cliffs, delivering sweeping panoramas of the area.
Elsewhere, guests will relish discovering the stunning crystalline formations hidden within Crystal Grottoes Caverns. This geological treasure lures guests underground for a unique trip, exposing dramatic limestone features formed over 500 million years ago.
Cumberland
Cumberland is a picturesque small city where visitors come to explore the alluring mountain scenery of Western Maryland. The region is known for its majestic outdoors, which you soak in during a historic train tour onboard the Western Maryland Scenic Railroad. This steam train excursion drags through the forested wilderness of the Allegheny Mountains, which looks otherworldly during the changing fall colors.
A historic downtown district houses many of Cumberland's well-preserved Victorian treasures. This includes the 1867 Gordon-Roberts House, which harbors authentic art, furnishings, toys, and other artifacts from the 19th century. Furthermore, you can connect with local arts at the Cumberland Theatre, an intimate spot for watching musicals, dramas, plays, and similar stage shows by homegrown performers.
Oakland
Oakland is a hidden gem in Garrett County, with spectacular natural landscapes and curious historical heritage. Many adventurers are drawn to Swallow Falls State Park, which lies along the banks of the Youghiogheny River. The reserve's peaceful nature trails expose you to breathtaking scenery, highlighted by the 53-foot Muddy Creek Falls and mature white pines and hemlock trees. Visitors with kids can take them to Alpaca Acres Farm and Fun for a family-friendly visit, where they get to interact with cute alpacas in a working farm.
Oakland is also known for its history, and the Garrett County Historical Society Museum attracts guests with over 200 years of heritage from the region's early days. The complex features three museums with wide-ranging displays highlighting different facets of the country's history.
Bel Air
This close-knit community in Harford County entices visitors with its adorable natural treasures and a handful of historical attractions. It is a pedestrian-friendly town square that hosts several landmarks that transport guests to the bygone eras, including the Liriodendron Mansion. Constructed in the late 1800s, this Palladian-style dwelling once housed Dr. Howard Kelly and his family. The Bel Air Farmer's Market breathes life into the downtown streets every Saturday as over 60 local vendors bring out their wares for sale. This offers a casual shopping opportunity, as well as fun-filled interactions with down-to-earth townsfolk.
Hike lovers can find comfortable walking shoes for a delightful adventure along the Ma and Pa Trail. Stretching just over six miles, the scenic route winds past lush woodlands and quiet creeks in the secluded Bel Air backcountry.
Westminster
Westminster serves as a popular small-town escape from the busyness of nearby Baltimore and Washington, D.C., offering a lovely combination of cozy green spaces and flavorful craft wine culture. Guests are welcome to commune with Mother Nature on the 320 acres of Bear Branch Nature Center. Set on the peaceful shores of Lake Hashawa, the oasis offers five miles of trails that allow you to explore its thriving flora and fauna.
While outside, use the chance to visit Serpent Ridge Vineyard and sample flavorful local wines. The establishment crafts award-winning varietals from locally grown grapes. Along Main Street in Westminster, spare a few hours for a cultural lesson at the Carroll County Arts Council. Here, you can attend a workshop to enhance your technique, browse an exhibition, or watch a live stage performance.
Chestertown
History meets the arts in this charming riverfront town of Kent County. Chestertown's Arts and Entertainment District hosts an eclectic blend of heritage sites, cultural venues, and entertainment joints worth checking out. This included the Garfield Center for the Arts, where the community finds mutual interest in the arts by supporting homegrown talent during electric stage performances. The community's rich past comes to life at the Historical Society of Kent Community, whose wide-ranging exhibits chronicle notable events in the town since its establishment in the 18th century.
Meanwhile, a trip to Safe Harbor Great Oak Landing exposes guests to the town's riverside charm. You can also get on the water for a nonchalant cruise down the Chester River on a yacht by booking a tour with Chester River Packet Company.
Havre De Grace
One of the most exciting small towns in Maryland, Havre de Grace boasts a picturesque setting on the mouth of the Susquehanna River as it pours into the Chesapeake Bay. This culminates in majestic water views, which first-timers can revel in from the serene vantage point of the Havre de Grace Promenade. From the platform, you will notice the towering Friends-Concord Point Lighthouse, a stark reminder of the town's long-lasting seafaring heritage. The structure was installed in 1827 and provides eye-opening educational tours exploring various historical artifacts.
Alternatively, guests can visit the Havre de Grace Maritime Museum for a deeper look into the region's fishing, oystering, and crabbing heritage over the years.
Ocean City
Sandwiched between the shimmering waters of the Isle of Wight Bay and the Atlantic Ocean, Ocean City enchants newcomers with its dramatic water views, miles of beach, and world-class amusement parks. Many come to let their hair down on the sandy stretch of Ocean City Beach. Boasting a 10-mile shoreline, the space is popular among swimmers, loungers, sunbathers, and picnickers. Also, the historic Ocean City Boardwalk presents a bustling corridor where guests can mingle and socialize with other visitors as they shop for cute souvenirs and enjoy tasty treats at many shops and restaurants.
Vacationing families will fancy a fun day out at the Jolly Roger Amusement Park. This exhilarating establishment offers everything from water slides and thrill rides to roller coasters and a Ferris wheel, ensuring all ages get a dose of the fun.
Cambridge
Established in the 17th century, Cambridge is one of the oldest communities on the Eastern Shore and is steeped in maritime heritage. Visitors can explore this at the Richardson Maritime Museum, whose vast catalog of artifacts documents over three centuries of local maritime history, focusing on outstanding boatbuilders and their vessels. The Choptank River Lighthouse underscores the town's nautical culture, standing out for its unique screw-pile design. It was constructed in 1871 to guide marine sailing along the Choptank River.
Some of the best views of the waterway await at Long Wharf Park. This serene riverside park provides a relaxing outdoor escape where vacationers can stroll along paved pathways to admire the scenery or find an isolated fishing spot to try their luck in the water.
Thurmont
Thurmont's unrivaled allure comes from its scenic natural scenery, thanks to its setting in the foothills of the Catoctin Mountains. Unsurprisingly, it is a popular getaway for ardent adventurers seeking to immerse themselves in the sprawling wilderness of Catoctin Mountain Park. Covering almost 6,000 acres, the reserve's rugged terrain is designed for hikers, backpackers, campers, and more.
Furthermore, Cunningham Falls State Park invites nature photographers to capture one of the most scintillating scenes in the state. The sanctuary houses Cunningham Falls, a 76-foot cascading wonder deemed to be Maryland's highest waterfall. Elsewhere, animal lovers have an opportunity to meet furry friends at the Catoctin Wildlife Preserve. The small zoo houses at least 300 wildlife species, including meerkats and zebras.
Final Thoughts
Every once in a while, it helps to seek reprieve from the constant chaos in the city by venturing into the peaceful spaces in the backcountry to rest and recharge. Whether going on a solo vacation to unwind or a family trip to spend quality time with loved ones, these small towns in Maryland provide the ideal destination for a memorable escape in the United States. They all have something unique to offer, from the riverside relaxation in Cambridge to downtown delight in Berlin.
