A great way to spend the day and get to know a town is to walk the streets. You can explore the sights, pop in the shops, and of course, eat at multiple places you pass along the way. We’ve rounded up some great recommendations from our readers on walkable small towns in Maryland; we’ve got can’t miss historic stops, delicious eats, and pretty scenery to enjoy.
Annapolis, Anne Arundel County
As the Maryland State Capital, Annapolis is pretty well known for its combination of history, life on the Chesapeake Bay, and top-rated restaurants to make everyone in your family happy.
Historical Hot Spot: “Make sure you go to the State House and go to the room where George Washington resigned his commission. There’s a great exhibit around his resignation and it explains the historic significance. Many wanted Washington to become the new king but instead he set us on the road to democratically elected presidents. This is a break with thousands of years of global history. Not to be missed.”
Food Recommendations: “Stop by Reynolds Tavern for a spot of tea and scones, Fox’s Den for pizza, Vida Taco Bar for tacos. Lots of places to choose from.”
Can’t Miss Scenery: “Walk along the water in Ego Alley on your way to City Dock. Take in the sights of tons of boats and a panoramic view of the Chesapeake Bay.”
Berlin, Worchester County
Located on the Eastern Shore of Maryland, Berlin is a quintessential small town. It’s walkable streets and historic streets make this town a favorite day trip destination because of its close proximity for those visiting the beaches near Ocean City.
Historical Hot Spot: 47 individual structures in Berlin are noted in the National Register of Historic Places and they represent nearly two centuries of architectural heritage.
Food recommendations: “I would recommend starting with appetizers at The Sterling Tavern, dinner at Blacksmith Berlin, and then dessert at Island Creamery.”
Can’t Miss Scenery: “Tree-lined streets and a Victorian town center, it’s pretty all year long.”
Boonsboro, Washington County
Known for its proximation to Antietam National Battlefield, Boonsboro is located at the foot of South Mountain, nearly bordering Frederick County. It’s a great small town with restaurants situated within a block of each other so makes for an easy afternoon stroll to get to know the town.
Historical Hot Spot: Antietam National Battlefield. Antietam National Battlefield is a National Park Service-protected area along Antietam Creek in Sharpsburg. It commemorates the American Civil War Battle of Antietam that occurred on September 17, 1862.
Food recommendations: “Jeovani’s Pizzeria and Stone Werks Coffee and Sweets are all wonderful. The Admiral has a great mocktail menu; it’s pricey but worth it.”
Can’t Miss Scenery: “Boonsboro is proud to be a member of the Appalachian Trail Community. Boonsboro is to west of the Appalachian Trail, and a popular spot for hikers to rest up, refresh, and enjoy the charming ambiance and hospitality of the town.”
Ellicott City, Howard County
Located not far from Patapsco Valley, Ellicott City has a historic small town vibe while being close to larger metropolitan areas like Baltimore and Columbia. It offers tons of great restaurants, local shopping, and plenty of parking so you’re sure to get out walking once you arrive.
Historical Hot Spot: Ellicott City was once one of the largest milling and manufacturing towns in the East and is considered by some as the home of the Industrial Revolution.
Food recommendations: Manor Hill Tavern is a brewery-owned restaurant with dishes made with local produce and serves craft beer. “If you are looking for mocktails, check out Umi Sushi.”
Can’t Miss Scenery: “If you are coming with kids, Ellicott City Station Museum, which is one of the oldest train stations in America, is a must see. Lots of visitors miss an amazing HO scale toy trains exhibit.”
Frederick, Frederick County
While Frederick does have its share of urban sprawl, Downtown Frederick has maintained its charm and historical roots. It is on the top of the list for walkable small towns in Maryland, known for its award-winning restaurants, annual events, and local shopping.
Historical Hot Spot: Francis Scott Key, the author of the United States National Anthem, is buried beneath the Francis Scott Key monument in Frederick, Maryland’s Mount Olivet Cemetery. Key wrote the lyrics while on board a ship during the bombardment of Fort McHenry (in nearby Baltimore). He had made notes for himself as he watched the bombardment, and these notes later became one of the most famous songs in the United States.
Food recommendations: “Firestone’s is my favorite by far. They have the Raw Bar with amazing oysters, plus the full menu at Firestone’s Culinary Tavern – they have a delicious brunch. And best of all, their Market on Market next door was the perfect place to pick up items like wine, cheese, and other specialty foods that made for an amazing picnic to eat in Carroll Creek Park.”
Can’t Miss Scenery: “Carroll Creek Park is Downtown Frederick’s most treasured attractions. This 1.5 mile-long park stretches through the center of the historic district, built atop the waters of Carroll Creek. The park has become a hub for unique public art, fountains, water gardens, lighted sailboats, live music, and community festivals, while also hosting a wide variety of restaurants, outdoor dining, breweries, and a distillery.”
Havre de Grace, Harford County
Named after a port city in France, Havre de Grace is located where the Susquehanna River meets the Chesapeake Bay. It is a charming historic town known for waterfront views, hiking trails, parks and museums.
Historical Hot Spot: The Concord Point Lighthouse is the second oldest lighthouse in Maryland that is still standing and it is the symbol of Havre de Grace. Built in 1827, the lighthouse served as a beacon for sailors in the Upper Chesapeake Bay. Located at the point where the Susquehanna River meets the Chesapeake Bay, the light was an active aid to navigation for 148 years. Today, the fully restored Lighthouse and Keeper’s House are both open to the public on weekends from April to October.
Food recommendations: “Abbey Burger was great and then ice cream at Bomboys Candy!” Other recommendations: Vineyard Wine Bar, Creole de Graw, and Les Petits Bisous.
Can’t Miss Scenery: “Walking the boardwalk was so lovely and relaxing.” The boardwalk is a leisurely stroll along the water, from Tydings Park, to the Concord Point Lighthouse. Along the boardwalk, signage has been erected that enhances your experience. You may encounter ducks, geese, osprey, and bald eagles during your stroll.
Leonardtown, St. Mary’s County
Not too far from St. Mary’s City, Maryland’s First Capital, sits the historical small town of Leonardtown. Its waterfront views are of Breton Bay which flows into the Potomac River. Leonardtown served as a busy port and steamboat landing until the passing of the steamboat era in the early 1900’s.
Historical Hot Spot: Leonardtown is perhaps most famous for the National Oyster-Shucking Championship that is held annually at the St. Mary’s County Fairgrounds every October. People from all over the world come to this festival to be crowned the Oyster-Shucker Winner.
Food recommendations: “It’s got The Slice House, Flour Donuts and Bakery, Social Coffeehouse, The Rex, Sweetbay, Smash House, Botanic Cafe, Brudergarten, The Salted Scoop, Heritage Chocolate, Olde Town Pub, and The Front Porch.”
Can’t Miss Scenery: “A walk down to the wharf or take the trolley ride for fun!”
St. Michaels, Talbot County
Some might know St. Michaels due to a popular hotel featured in a movie but there is more to this charming Eastern Shore town than the Inn at Perry Cabin (though it deserves its wonderful reputation and is highly recommended if you’re looking to splurge a bit). It is a bustling town full of eateries, antique shops, homemade goodies, and a charming vacation vibe.
Historical Hot Spot: In 1813 during the War of 1812, the British bombarded the town from barges and a brig, but failed to destroy the shipyards or cause any substantial damage to the town. Reports say that the town was spared because they dimmed the lights within the town and instead hung lanterns in the trees outside of town thus sparing St. Michaels. Based on this story, St. Michaels became known as ‘the town that fooled the British,’ and The Cannonball House survives as one of the structures reportedly struck by one of the shots, and is on the National Register of Historic Places, as is the Saint Michaels Historic District.
Food recommendations: “Gina’s for appetizers, then on to Ava’s for dinner, and top it off with Limoncello for dessert!”
Can’t Miss Scenery: “Sitting right on the water, the Chesapeake Bay Maritime Museum is definitely a must-see! Great exhibits and so much knowledge about the history of the Chesapeake Bay.”
Sykesville, Carroll County
Once known as the “Coolest Small Town” in America by Budget Travel Magazine and “Best Main Street in America” by Independent We Stand, Sykesville is a busy town with historic charm, scenic views, and strong community bonds. The town is nearby several outdoor opportunities so perfect for nature lovers.
Historic Hot Spot: Sykesville Main Street hosts several events throughout the year, including Art & Wine Festival, Farmer’s Market, Pride Day, Juneteenth, July 4th Parade, Fall Fun Festival, and more!
Food recommendations: “Start at 7556 Main Street Bistro for appetizers (make sure you order the shrimp garlic boat – it is to die for!). Local Motive is great for a main course and finish it off at E.W. Becks for dessert. And for breakfast the next day, check out The French Twist for fabulous crepes.”
Can’t Miss Scenery: Sykesville is known for its many springs which dot the hills on the north side of the Patapsco river.
Whether it’s boots, sneakers, or flip-flops, they are all made for walking so we hope you enjoy your walkabouts in these great small towns!