From the rocky majesty of the Allegheny Mountains in Western Maryland to the sandy beaches and rural splendor of the Eastern Shore, Maryland offers a little something for everyone.
For this annual issue of “O Say, Have You Seen … Maryland,” we selected five small towns from each section of the state that are within driving range of the Baltimore metropolitan area and help explain why Maryland is often called “America in Miniature.”
Berlin
It’s no wonder why Smithsonian magazine named Berlin one of the best small towns to visit in the nation, while the Budget Travel website dubbed the Eastern Shore hamlet “the coolest small town in America.”
Located in Worcester County about nine miles from Ocean City, Berlin (pop. 4,485) is a scenic small town brimming with more than 60 shops, galleries, antiques emporiums, restaurants, breweries, live music venues, markets, bakeries and java joints.
If history is your passion, drop by the Calvin B. Taylor House Museum, the repository for all things historic in Berlin. And by all means, check out Berlin’s quaint Main Street district, which features nearly 50 structures on the National Register of Historic Places.
Incorporated as a town in 1868, Berlin’s historic districts feature nearly two centuries of architectural heritage from the Federal, Victorian and 20th-Century periods.
BTW, a pair of Hollywood flicks were filmed in and around Berlin: 1999’s “Runaway Bride” starring Julia Roberts and Richard Gere, and 2002’s “Tuck Everlasting” with Sissy Spacek, William Hurt and Ben Kingsley. Not too shabby!
For information, visit berlinmainstreet.com.

Frederick
No one around these parts could’ve been too shocked when Money magazine earlier this year placed Frederick on its annual list of best places to live in the nation.
After all, the historic Western Maryland town (pop. 82,175) — within easy driving distance to Charm City and D.C. — has made many prestigious lists over the years as an ideal place to live … and visit.
Oldtimers can still recall a time when Frederick was known as a hardscrabble town that was, shall we say, a bit rough around the edges. But that was decades ago, and the renaissance of Frederick (aka, “the City of the Clustered Spires”) is nothing short of miraculous.
Located where the Catoctins meet the rolling hills of the Piedmont region, Frederick boasts a rich history, a thriving arts and entertainment life, and seemingly countless trendy, chi-chi shops and restaurants.
Morbid as it might sound, don’t miss the National Museum of Civil War Medicine, at 48 East Patrick Street. Yes, the subject is grim, but the museum’s exhibits show how the war changed the face of medicine and the nation, and address such issues as triage, evacuation of wounded from battlefronts, and tools and equipment used during the conflict.
But if limb amputations just don’t sound like your thing, Frederick also boasts a surplus of hip coffee spots, tchotchke stores, an array of high-end dining establishments, pubs and a fabulous canal walkway that leads to spectacular Carroll Creek Park.
And if you need a cool place to stay, why not check out the Barbara Fritchie House, an historic landmark that has been renovated as an AirBnb (and is reportedly the site of supernatural activities)?
For information, visit visitfrederick.org.
Havre de Grace
Havre de Grace means “harbor of grace” in French, and this lovely Harford County river town certainly lives up to its billing.
HdG — as locals call it — has it all: a scenic waterfront and promenade, gorgeous older homes, and a charming main street brimming with trendy stores and restaurants.
All only a 45-minute drive from Baltimore!
Founded in 1782, Havre de Grace (pop. 14,996) is situated at the mouth of the Susquehanna River and the head of the Chesapeake Bay. (Fun fact: During the 1st United States Congress in 1789, HdG was only a single vote from being designated the capital of the United States. It lost to Philly.)
Just walking around HdG is an intoxicating experience. But among the places you might want to drop by are the Havre de Grace Decoy Museum, which celebrates the unique American folk art of decoy carving; the Bahoukas Antique Mall and Beer MuZeum, with its vast collection of bar signs, glasses, steins, tap handles and more; the ever-quirky Washington Street Books & Entertainment Museum, which offers an extensive comic book collection and encased costumes from a variety of movies; and of course, the Concord Point Lighthouse & Keeper’s House Museum at the foot of the town’s Promenade. Built in 1827, Concord Point is the oldest continuously operated lighthouse in Maryland and has a spectacular view of the bay.
Meanwhile, stop by Bomboy’s Homemade Ice Cream and Candy to sample the sweet side of HdG before your return home to Baltimore.
For information, visit explorehavredegrace.com.
Leonardtown
Seriously, how many small towns can claim a rock rumored to be the final resting place of a suspected sorceress as one of its leading tourist attractions?
The St. Mary’s County seat nestled on the banks of the Potomac, Leonardtown (pop. 49,055) is a peaceful and charming slice of Southern Maryland. Located within driving distance to Calvert Cliffs State Park and the picturesque boating town of Solomons Island, Leonardtown has to plenty to offer — shops, restaurants, bookstores, galleries, coffee spots, and a quaint town square and historic district that will transport you back in time.
There’s also the picturesque Leonardtown Wharf waterfront, which opened in May 2008 and is a great place to kayak, paddleboard or simply walk around and take in sublime sunsets. You might also want to check out the Port of Leonardtown Winery, which features locally grown grapes. And by all means, don’t miss the Piney Point Lighthouse Museum and Historic Park, only a 20-minute drive from L-Town.
Not to be overlooked is the Moll Dyer Rock, on which a suspected 17th-century witch was found frozen to death. Legend has it that you can still see the imprint of Moll’s hands and knees on the rock, which is now located outside of Tudor Hall, home to the St. Mary’s County Historical Society. A thick pane of glass protects the rock from the elements, and a closed-circuit camera keeps an eye on visitors who drop off flowers, candles and spare change.
Oh, and if you get a chance, check out “Moll Dyer Day,” held every February in Leonardtown. It always proves to be a bewitching time to see Leonardtown in all of its glory.
For information, visit visitleonardtownmd.com.

Oakland
No, the railroad doesn’t come through Oakland (pop. 1,851) much anymore. But there is a proud train tradition and legacy in this town, the Garrett County seat, that just begs to be explored.
Oakland is the home of the Oakland B&O Museum & Train Station, which was listed on the National Register of Historic Places. The museum features a 1920s-era Baldwin steam locomotive. There’s also the nearby Garrett County Transportation Museum, which showcases historic vehicles, fire trucks, boats, buggies, carriages, sleighs and snowmobiles.
Oakland is also the home of the county’s Arts & Entertainment Districts, and serves as the home base for the Garrett County Arts Council and its gallery shop, where visitors can purchase locally produced artwork.
There are also plenty of shops and restaurants in historic downtown Oakland. Not to be missed is Englander’s, an antiques store and old-style soda fountain/luncheonette.
For the more outdoorsy and rugged at heart, Oakland is only a short drive away from Deep Creek Lake, Swallow Falls State Park, Herrington Manor State Park and Backbone Mountain, which features the Hoye-Crest summit, the highest point in Maryland. —Alan Feiler
For information, visit visitdeepcreek.com/oakland.

