9 Charming Maryland Towns For The Perfect Getaway
Maryland is home to a wealth of charming towns that show off some of the Mid-Atlantic's most stunning scenery. In St. Michaels, a walkable harborfront and the Chesapeake Bay Maritime Museum create the kind of waterfront charm that is hard to resist. In Berlin, tree-lined streets and a Victorian downtown make the town feel tailor-made for a charming visit. And in Havre de Grace, the waterfront setting and walkable parks are perfect for a getaway. Below are 9 of Maryland's cutest towns.
St. Michaels
St. Michaels’ history goes back to the mid-1600s. It was once a trading post for trappers and tobacco farmers, and its shipyards made it a major target for the British during the War of 1812.
St. Michaels has plenty of shops, museums, restaurants, and places to stay. One highlight for learning about 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, including Navy Point and the historic Hooper Strait Lighthouse, has the largest collection of Chesapeake Bay artifacts anywhere.
Shop at Antiques on Talbot, grab a drink at Blue Heron Coffee, the longest-operated brewery on the Eastern Shore, or learn more about the town’s past on a 65-foot vessel with Patriot Cruises.
Berlin
This attractive town in Worcester County stands out for its tree-lined streets, historic homes, and Victorian downtown filled with beautiful brick buildings. A remarkable 47 structures are listed on the National Register of Historic Places, representing nearly two centuries of architectural history.
Berlin is clearly a strong shopping destination, which helped it earn the title of America’s Best Small Town for Shopping from USA Today. More than 60 galleries, shops, and restaurants line Downtown Berlin, including 410 Social, The Treasure Chest, and Stuarts Antiques. Visitors can also learn about Berlin’s past at the second-floor gallery of the Federal-style Taylor House Museum, built in 1832. Berlin also appeared in two popular films: "Runaway Bride" with Julia Roberts and Richard Gere, and "Tuck Everlasting." With so much to do, it is easy to see why Budget Travel Magazine named Berlin America’s Coolest Small Town. For a place to stay, the restored Atlantic Hotel offers 15 comfortable rooms, a bistro bar, and a ballroom in its 1895 style.
Chestertown
Founded in 1706, Chestertown became a major trade hub because of its location on the Chester River, and it was named 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 the place where Washington College, the first college founded in the newly independent United States, was established eight years later.
Chestertown’s town center is full of charm and has the second-largest district of restored 18th-century homes in Maryland. The brick sidewalks, lively restaurants, antique stores, and comfortable inns make it an inviting place to explore.
Browse handmade goods and fresh produce at Chestertown Farmers’ Market. Or explore maritime history on the Schooner Sultana, a full-scale replica of a 1768 ship used by the British Royal Navy to collect tea taxes. After a full day, stay at the White Swan Tavern, a restored colonial inn with six lovely rooms and a hot breakfast.
Easton
The charming small town of Easton has art galleries, boutiques, fun activities, and many restaurants, all while being close to major metro areas like Annapolis, Baltimore, Philadelphia, Washington, D.C., and Wilmington.
Events take place year-round, including 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. Culture lovers will also enjoy places like the Talbot Historical Society, Academy Art Museum, and Avalon Theatre.
Visit the James Neal House, built in 1804, to see Federal architecture from the years after the Revolutionary War. Golfers can play at Hog Neck Golf Course, which has been rated one of the top courses in the country. With creeks and rivers on every side, Easton is also great for fishing and boating. Food lovers will find plenty of dining choices, from casual meals to fine dining. The Tidewater Inn, which combines traditional decor with modern amenities, is a great base for exploring downtown Easton.
Cambridge
Located on the wide Choptank River, Cambridge is the county seat of Dorchester and dates to 1684, making it one of the oldest colonial cities in the state. Many of the elegant homes along High Street, a broad 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 honors the famous abolitionist and social activist with immersive exhibits.
Blackwater National Wildlife Refuge covers more than 40 square miles and is home to over 250 species of birds, making it a beautiful place for paddling, biking, or hiking. You can also explore 300 years of maritime history at the Richardson Maritime Museum before eating at places like Boats & Hose, Carol’s Kitchen, or Paul’s Pub Bar & Grill.
You can enjoy wide water views from the Choptank River Lighthouse, a replica of the historic structure that once guided mariners along the river. Cambridge House Bed & Breakfast, within walking distance of downtown, offers a restful place to stay.
Havre de Grace
Tucked where the Susquehanna River meets the 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 and is the oldest publicly accessible lighthouse on the Chesapeake Bay.
You can learn about the city’s past at the Keeper’s House Museum. For more on the area’s maritime history, visit the Havre de Grace Maritime Museum, which sits among local plant and animal life. The Living War Memorial Museum also honors the nurses, troops, and support staff who served in every U.S. war. You can also see public art at Concord Point Park or enjoy a show at The Cultural Center at the Opera House.
The Vandiver Inn has been part of the town since 1886 and combines the charm of a country inn with the feel of a downtown boutique stay.
Frederick
Frederick County was formed in 1748 from the western part of Prince George’s County. Before colonial settlement, the land was home to the Piscataway and Tuscarora Nations. Today, with more than 200 downtown art galleries, specialty shops, restaurants, and distilleries, Frederick is a town you should not overlook.
It is the final resting place of Francis Scott Key, who wrote the lyrics to the U.S. national anthem. It has also welcomed figures such as George Washington, Abraham Lincoln, Benjamin Franklin, the Marquis de Lafayette, and Winston Churchill. Civil War fans will enjoy the National Museum of Civil War Medicine and Monocacy National Battlefield.
At Rose Hill Manor Park & Museums, you can see where Maryland’s first elected Governor, Thomas Johnson, spent his retirement. The Museum of Frederick County History is also worth a stop for its exhibits, public programs, guided tour options, and beautiful garden.
For a break from the history, take a stroll around 0.85-mile Carroll Creek Park. Then spend the night at the 10 Clarke Hotel, a charming Victorian inn that includes a three-course gourmet breakfast with every room.
Boonsboro
George and William Boone, cousins of frontiersman and pioneer Daniel Boone, founded Boonsboro in 1792, though the town was not incorporated until 1831.
Shafer Memorial Park hosts several major public events, including The Founder’s Day Celebration, which takes place with the National Pike Festival.
The first completed monument dedicated to George Washington stands in Washington Monument State Park atop South Mountain and is a great place for birdwatching. Visit the Washington Monument Museum to see artifacts and displays about the rugged stone monument built in 1827.
The National Road Museum tells the story of the Historic National Road Scenic Byway, while the Boonsboro Trolley Station Museum focuses on the Hagerstown & Frederick Railway. The Boonesborough Museum of History also has an extensive Civil War collection.
The town has several quaint shops and restaurants, including Turn the Page Bookstore, where you can relax with a cup of coffee. You can also stay at Inn Boonsboro, a 200-year-old property now owned by author Nora Roberts and her husband Bruce Wilder, who also owns the bookstore. It combines the comfort of a bed and breakfast with the style of a boutique hotel.
Berwyn Heights
Incorporated in 1896, the town of Berwyn Heights sits on the eastern slopes of the Indian Creek Valley in Prince George's County. Before settlement, the area was occupied by a native people called the Anacostanks and later became home to Scottish emigrants during the American Revolution.
With about 3,100 residents, Berwyn Heights has a strong sense of community, and its peaceful setting offers a nice break from the busy pace of nearby Washington, D.C., Baltimore, and Philadelphia.
Airplane fans should not miss the College Park Aviation Museum, which celebrates the history of College Park Airport, the world’s oldest continuously operating airport. Lake Artemesia Natural Area is also a great place for hiking, fishing, and picnics.
You may also want to walk off a meal from Tacos A La Madre or Mission BBQ while you are there. Afterward, relax at The Hotel at The University of Maryland, a AAA Four-Diamond property with comfortable rooms, a heated indoor pool, a fitness center, and several dining options.
Maryland’s Majestic Towns Are Calling
These nine towns in The Old Line State offer a wonderful mix of culture, history, and natural beauty, making them great picks for a memorable getaway. Whether you are enjoying local food, exploring historic sites, or relaxing at a charming inn, each of these Maryland towns has plenty to offer. Pack your bags and get ready to discover these wonderful places.
