9 Charming Maryland Towns For The Perfect Getaway
Located in the Mid-Atlantic region of the United States, Maryland is home to a wealth of charming towns that provide an ideal mix of history, culture, and scenic beauty. Whether you're a history buff, a nature lover, or simply in search of a tranquil retreat, these towns have something for everyone. From museums and historic landmarks to quaint shops and cozy accommodations, each town provides a unique experience that will undoubtedly transport you back in time. Here are nine marvelous Maryland towns that make perfect destinations for your next getaway.
St. Michaels
St. Michaels’ history dates to the mid-1600s. It once as a trading post for trappers and tobacco farmers, ajnd its shipyards rendered it a prime target of the British during the War of 1812.
St. Michaels has no shortage of shops, museums, restaurants, and accommodations from which to choose. Highlighting life in the mid-19th century is the three-building St. Michaels Museum, which offers docent-led walking tours on Saturday mornings. The Chesapeake Bay Maritime Museum’s 18-acre waterfront campus, which includes Navy Point and the historic Hooper Strait Lighthouse, features the most comprehensive collection of Chesapeake Bay artifacts anywhere.
Come away with a great find at Antiques on Talbot; fuel up at Blue Heron Coffee, the longest-operated brewery on the Eastern Shore; or learn more about the town’s history on a 65-foot vessel with Patriot Cruises.
Berlin
This handsome town in Worcester County will dazzle you with its tree-lined streets, historic homes, and a Victorian town center punctuated by beautiful brick buildings. Representing almost two centuries of architectural heritage are a whopping 47 structures listed on the National Register of Historic Places.
It’s easy to see why Berlin was named America’s Best Small Town for Shopping by USA Today: From 410 Social and The Treasure Chest to Stuarts Antiques, over 60 galleries, restaurants, and shops line Downtown Berlin. Be sure to learn all about Berlin’s past at the second-floor gallery of the Federal-style Taylor House Museum, which was built in 1832.
Berlin has even been the setting for two popular movies: Runaway Bride starring Julia Roberts and Richard Gere, and Tuck Everlasting. With so much to see and do here, it’s no wonder Berlin was recognized as America’s Coolest Small Town by Budget Travel Magazine. For lodging, check out The Atlantic Hotel, which was recently restored to its 1895 appearance and includes 15 comfortable rooms, bistro bar, and a ballroom.
Chestertown
Founded in 1706, Chestertown’s location on the Chester River made it a major trade hub, and it was designated as one of Maryland’s six Royal Ports of Entry. In 1774, Chestertown hosted the Chestertown Tea Party, a protest against British excise duties. It was also here that Washington College - the first college founded in the newly independent United States - was established just eight years later.
Brimming with charm is Chestertown’s town center, the second-largest district of restored 18th-century homes in Maryland. The town’s attractive brick sidewalks, lively restaurants, interesting antiques, and comfortable inns beckon you to browse, delight your palate, and make yourself right at home.
Immerse yourself in local culture at Chestertown Farmers’ Market, where you can pick up handmade goods and fresh produce. Or, soak up maritime history aboard the Schooner Sultana, a full-scale reproduction of a 1768 vessel of the same name used by the British Royal Navy to enforce the previously mentioned tea taxes. After a long day, check into the White Swan Tavern, a restored colonial-era inn offering six beautifully decorated rooms and hot breakfast.
Easton
The idyllic small town of Easton offers eclectic art galleries, fine boutiques, fun-filled activities, and a wide array of restaurants - all while being conveniently close to large metro areas like Annapolis, Baltimore, Philadelphia, Washington, D.C., and Wilmington.
Year-round programming includes a St. Patrick’s Day parade, Easter egg hunt, a Gallery Walk on the first Friday of every month, an annual Waterfowl Festival, and a Fire and Ice Festival. With places like the Talbot Historical Society, Academy Art Museum, and Avalon Theatre, culture enthusiasts are in for a treat.
Pay a visit to the James Neal House, built in 1804 and representing the Federal architecture common in the years that immediately followed the Revolutionary War. Avid golfers can tee off at the Hog Neck Golf Course, rated one of the best courses in the United States. Creeks and rivers surround Easton on every side, making it a prime location for fishing and boating. Foodies also have their choice of eateries, whether they’re up for casual or fine dining. Coupling traditional décor and modern amenities, the Tidewater Inn makes an ideal base from which to explore downtown Easton.
Cambridge
Situated on the broad Choptank River, Cambridge, the seat of Dorchester County, dates to 1684, making it one of the oldest colonial cities in the state. Many of the stately homes on High Street, a wide brick-paved road lined with tall trees and striking architecture, date from the 1700s and 1800s. The Harriet Tubman Underground Railroad State Park and Visitor Center pays tribute to the famous abolitionist and social activist through immersive exhibits.
Covering over 40 square miles and home to more than 250 species of birds, the expansive Blackwater National Wildlife Refuge provides wonderful scenery for paddling, biking, or hiking. You can also delve into 300 years of maritime history at the Richardson Maritime Museum before grabbing a bite at excellent dining spots like Boats & Hose, Carol’s Kitchen, or Paul’s Pub Bar & Grill.
Panoramic water views can be had from the Choptank River Lighthouse, a replica of the historic structure that once guided mariners along the river. A restful night’s sleep awaits at Cambridge House Bed & Breakfast, within walking distance of downtown.
Havre de Grace
Tucked at the confluence of the Susquehanna River and Chesapeake Bay, Havre de Grace is a scenic historic town known for its museums, festivals, waterfront views, entertainment venues, trails, and parks. The Concord Point Lighthouse was built in 1827, making it the oldest publicly accessible lighthouse on the Chesapeake Bay.
Exhibits chronicling the landmark’s history can be found at the Keeper’s House Museum. For more context around the area’s rich maritime history, look no further than the illuminating artifacts housed in the Havre de Grace Maritime Museum, which is set amidst numerous species of fauna and flora. Moreover, the Living War Memorial Museum honors the valiant nurses, troops, and support staff who have served in all wars that the U.S. has taken part in. Check out public art installations at Concord Point Park or catch theatrical performances at The Cultural Center at the Opera House.
Melding the charm of a country inn and the appeal of a downtown boutique property, the Vandiver Inn has graced the small town since 1886.
Frederick
Frederick County was formed in 1748 out of the western portion of Prince George’s County. Before colonial settlement, the land was inhabited by the Piscataway and Tuscarora Nations. Today, with over 200 downtown art galleries, specialty shops, restaurants, and distilleries, Frederick is a town you definitely don’t want to sleep on.
It is the final resting place of Francis Scott Key, who penned the lyrics to the U.S. national anthem. It has also played host to such notable figures as George Washington, Abraham Lincoln, Benjamin Franklin, the Marquis de Lafayette, and Winston Churchill. Civil War buffs will appreciate the National Museum of Civil War Medicine along with the Monocacy National Battlefield.
At Rose Hill Manor Park & Museums, you’ll experience firsthand where Maryland’s first elected Governor, Thomas Johnson, spent his retirement. Plus, an array of interesting exhibits, public programs, optional guided tours, and a beautiful garden make the Museum of Frederick County History a can’t-miss stop.
Want a little break from all that history? Take a leisurely stroll around 0.85-mile Carroll Creek Park before retiring for the night at an inn at 10 Clarke Hotel, a charming Victorian that includes a three-course gourmet breakfast in all of its room rates.
Boonsboro
George and William Boone, cousins of frontiersman and pioneer Daniel Boone, founded Boonsboro in 1792, though it wasn’t until 1831 that the town was incorporated.
Shafer Memorial Park hosts a number of major public events including The Founder’s Day Celebration, which coincides with the National Pike Festival.
The first completed monument dedicated to the memory of George Washington graces Washington Monument State Park, which lies atop South Mountain and makes an ideal place for bird watching. Visit the Washington Monument Museum to see artifacts and displays about the history of the rugged stone monument erected in 1827.
The National Road Museum tells the intriguing story of the Historic National Road Scenic Byway while the Boonsboro Trolley Station Museum sheds light on the Hagerstown & Frederick Railway. Plus, the Boonesborough Museum of History houses an extensive Civil War collection.
Several quaint shops and restaurants are on offer, as in Turn the Page Bookstore, where you can read and relax over a great cup of coffee. You can also disconnect at Inn Boonsboro, a 200-year-old property now owned by author Nora Roberts and husband Bruce Wilder (who also owns the bookstore) that combines the warmth of a bed and breakfast and the elegance of a boutique hotel.
Berwyn Heights
Incorporated in 1896, the town of Berwyn Heights is situated on the eastern slopes of the Indian Creek Valley in Prince George's County. Before settlement, it was occupied by a native people called the Anacostanks and later home to Scottish emigrants during the American Revolution.
With roughly 3,100 residents, Berwyn Heights enjoys a strong sense of community, its tranquil surroundings making a welcome respite from the hustle and bustle of nearby Washington, D.C., Baltimore, and Philadelphia.
Airplane aficionados won’t want to miss the College Park Aviation Museum, which celebrates the history of College Park Airport - the world’s oldest continuously operating airport. Perfect for hiking, fishing, and picnics is the Lake Artemesia Natural Area.
Perhaps you’ll also want to walk off a delicious meal from Tacos A La Madre or Mission BBQ while you’re there. Afterwards, indulge in complete comfort at The Hotel at The University of Maryland, a AAA Four-Diamond jewel offering well-appointed accommodations, a heated indoor pool and fitness center, and various dining options.
Maryland’s Majestic Towns Are Calling
These nine towns in The Old Line State offer a delightful blend of culture, history, and natural surroundings, making them fantastic spots for a memorable getaway. Whether you're enjoying local fare, exploring historic landmarks, or simply unwinding in a charming inn, you'll find plenty to love in each of these Maryland gems. So pack your bags and get ready to discover all that these wonderful towns have to offer!
