Maryland is the destination for adventurers and sight-seekers, thanks to its abundance of lighthouses, boardwalks, and small, vibrant towns with lots of character. The "Free State" stays true to its name, with hotspots for any taste to find freedom from the city walls and sounds. It is also the ideal gateway to the Chesapeake Bay, the largest estuary in the United States and the third largest in the world. This semi-enclosed coastal body of water comprises a blend of fresh water from inland rivers and oceanic salt water and offers easy access into the sea. These nine must-visit towns are particularly charming, with a magical pull that attracts nation-wide tourists and globetrotters.
If you are a guilty foodie or a shopaholic, head to Bel Air where you will never be judged in the town catering to like-minded "sinners." The historically charming small town in northern Maryland is only 45 minutes north of Baltimore for a quick hop into your favorite pursuits on a weekend. It attracts tourists from outside the state because of the abundance of downtown shopping opportunities that few other similar places can match.
There are a ton of local boutiques for one-of-a-kind pieces, as well as dining places to replenish your strength and keep powering through all the sights. Enjoy various dining options and grab a beer at one of the many breweries. This former underground railroad stop along the eastern coast is now a hotspot for tourists with vibrant attractions. After the modern-day pursuits, explore the town's history via a tour at the Hays-Heighe house on the campus of Harford Community College, just a few miles out of downtown.
The small town of Berlin has a special atmosphere and sits nestled only 10 miles from Ocean City amidst the refreshing scenery of the idyllic eastern Maryland countryside. Berlin's charming streets are lined by historic buildings, in-between shops with unique treasures, and delectable restaurants for all styles of dining. The art fans will also find their piece of heaven, particularly every second Friday on an art stroll.
Enjoy this vibrant event filled with live music and art displays you can admire or shop for souvenirs and home collectibles. The town's line-up of annual festivals makes it hard not to stumble upon an event during your visit. Enjoy a variety of outdoor events, such as concerts in the park or the popular peach festival, during the scenic fall season.
The town of only 1,000 is deserving of its big name. Chesapeake City is the model for small town charm, with a ton of cool local pursuits amidst relaxation and strolls along the scenic banks. The downtown, replete with hotspots amidst the many mom-and-pop stores, cute cafes, and unique shops, is just minutes away from the outdoors. Head to Lums Pond State Park with a kayak for warm-weather adventures along the coast.
Visit the C&D Canal Museum for some culturally scenic time or jog along the Ben Cardin C&D Canal Trail. Head to nearby North Beach One, which has an impressive stretch that is popular with vacationers and is ideal for a quaint family time picnic by the kid-friendly waters. The beach captivates with a relaxing vibe that makes it hard to leave after a fun day of splashing and sunbathing.
Another Eastern Shore town in Maryland has deep roots, particularly in the events during the Revolution, with the vibe still ringing through the sights. Chestertown boasts well-preserved colonial-era architecture, like its historic Courthouse, Town Hall, and Fountain Park. Step away from history and immerse yourself in scenic nature with maritime views at the two waterfront parks. Hop on a sightseeing cruise and see the charming town in a whole new light. Revel in the classic Chestertown experience aboard The Sultana, which lets you have a go at navigating the boat around the Bay and trimming the sails. The graceful Victorian mansions evoke the once-wealthy community, which is now accessible to anyone on a budget for a weekend getaway.
With so much to see, it is a good idea to take a walking tour around town to get familiar with the streetscape and the names of historic sights. Enjoy the youthful ring in the air emanating from the campus of Washington College. Chestertown is even more visually appealing during the holidays, with decorated streets and outdoor activities year-round. Join in the fun festivals for all interests, like the annual Tea Party Festival and Parade, the Dickens Christmas events, and the Classic Cars Show. Have an adventure exploring the secret coves and waterways via a kayak or biking down the quaint roadways flanked by farmland. Immerse yourself in the local lifestyle while tasting your way through the busy farmers market, followed by a real meal at one of the many farm-to-table restaurants.
It is difficult to find a more ideal town for any type of vacation, with a plethora of state parks nearby and all the amenities you could want on a modern getaway today. Crisfield takes another step forward with a particularly charming streetscape on the Chesapeake Bay's banks, lined by local dining and shopping options amidst many adorable AirBnB all the way to the outskirts. You can step out of the door and into the nature of the famed Janes State Park.
Spend a day or two in Mother Nature's gentle embrace at the State Park with a genuinely outdoorsy spirit. Revel in pursuits like camping, fishing, hiking, wildlife sightings, or simple relaxation in the shade. You can also stay for a camping weekend or head back to the city for a good night’s rest before seeking more sights in nature the next day. Choose a waterside stay, and you will have maritime views from the window.
Havre de Grace
The town with an idyllic name exudes peace from every pore. Havre de Grace is an ideal getaway into true tranquility to enjoy your favorite pursuits through food, history, or shopping. This charming little hotspot nestled along the scenic coast of the Susquehanna River in northern Maryland is right on top of the Chesapeake Bay. Havre de Grace beckons tourists just with its promenade alone, leading to the magnificent Friends-Concord Point Lighthouse. It is hard to take your eyes off such pleasingly heartbreaking scenery, found nowhere else in the state.
Relax, take photos, and visit its impressive museum and gift shop with unique local finds. Seafood lovers rejoice when they visit Havre de Grace, which is dotted with some of the best restaurants for sea delicacies within hundreds of miles. Start with a portion of clam chowder or dive into a bucket of steamed crabs or oysters with a waterfront view during the meal of a lifetime. Visit some of the downtown cafes in the morning and feel all tension seep away as you absorb the amazing flavors of the Chesapeake area.
Find this familiar-sounding town a stone's throw away from Washington, D.C., on a quick getaway into a small town with beautiful sights. Kensington has long been one of Maryland’s most aesthetically pleasing hotspots to relax amidst scenic views and engage in lighthearted pursuits. The charming town is also a destination for northeast travelers and globetrotters looking to immerse themselves in one-of-a-kind beauty.
The town along Rock Creek, one of the most impressive natural wonders, is right off a picture book page. Have a picnic along the banks and sight a chance deer grazing just a few meters away, used to the goggling tourists. Enjoy views of the steadily flowing waters, carrying all of your worries away with the current. Find a shady spot under a green canopy tree on a summer day and have a siesta, while the adventurous hike the Sligo Creek Trail, leading to a scenic denouement.
St. Michaels is the epitome of Maryland's staple boat town on crystal-clear waters. Take one of the staggeringly impressive vessels on a journey around the bay, throwing glances back at the charming townscape behind. Set a picnic on the shores and enjoy the gentle sounds of the lapping waters right at your feet, beckoning you to dive right in. The downtown is one big year-round celebration with demonstrations, exhibits, museums, and tourist firms promoting maritime activities like sailing and boating lessons. This beacon town for all water-related pursuits also boasts an impressive 1879 Hooper Straight Lighthouse.
It is a long-time, beautifully preserved benchmark to see while you are swimming in the blue and reminisce of the time when the calm waters of the Chesapeake along this shore were the "it" national destination. Even before that, the little picturesque town, once a busy seaport on the eastern shore of Maryland, has now turned into a shopping hotspot with unique stores along Talbot Street. Others visit for a wine-soaked respite at a nearby winery or while cruising around the harbor and through the bay. Seek out street sights with a long nautical history and pay a visit to the Chesapeake Bay Maritime Museum, which features an 18-acre waterfront, outdoor and indoor exhibitions, and a marina.
"The Gateway to the Mountains" on the border with Pennsylvania is the ideal contender for the cutest town in the nation. The small town at the foothills of the Catoctin Mountains is the illicit leeway to Camp David, the Presidential Retreat in Central, Maryland. It is also a national getaway into the breathtaking Cunningham Falls State Park, which has beautiful waterfalls and access to the Appalachian Trail. Thurmont is a real ethereal place with impeccable sights around each corner of the idyllic tree-lined streets, along with the nearby Catoctin Mountain Park for the adventurous. Find this charmer just fifteen minutes north of Frederick or half an hour south of Gettysburg.
The charming Main Street is lined by various shops, antiques, and art, along with the downtown farmers market with fresh fruit and vegetables right from the dozens of surrounding farms. Seek out the Springfield Manor Winery and Distillery in Thurmont during the very Instagrammable Lavender Festival. Take a stroll through its sprawling Catoctin Breeze Vineyard to an outdoor patio with acres of grapevine views. Explore the rest of the town's offerings by taking a bike ride along the paved Thurmont Trolley Trail and looking for the three beautiful covered bridges in the area. The Old Mink Farm features a petting zoo and hay rides, while the Catoctin Wildlife Preserve offers a safari adventure. The Cunningham Falls Lake is perfect for kayaking, while the imminent annual Maple Syrup Festival will turn 53 years old this March.
These charming towns provide a memorable escape to the endlessly scenic Chesapeake Bay. With so much to see in each, you can start with an introductory stroll through the downtown or along the many scenic boardwalks. Enjoy the lively vibe amidst the small town atmosphere while mingling with world-wide tourists and sharing a drink at the bar to hear both local tales and stories of far-away lands. You won't even feel envious of those who travel overseas on vacation while in one of these towns, surrounded by the beauty of the state that is most treasured in your heart.