10 Stress-Free Maryland Towns For A Weekend Retreat
A good weekend in Maryland does not take a week to plan. These ten towns sit close enough to reach on a Friday and full enough to fill a Saturday and Sunday. You can climb to Muddy Creek Falls in Oakland in the morning and crack blue crabs on the water in St. Michaels by night. Some are river towns, some are mountain towns, and a few sit right on the bay. Each one makes it easy to unwind without running out of things to do in Maryland.
Berlin
Berlin packs more than 60 independent shops into a walkable downtown, and it has the awards to prove it. Budget Travel named it America's Coolest Small Town, and its Main Street has landed on national best-shopping and best-main-street lists more than once. Start a slow morning at The Greyhound Indie Bookstore, run by a couple who list their greyhounds as staff and stock Eastern Shore writers. A block away, The Mermaid Museum keeps playful exhibits, costume stations, and a preserved mermaid-shaped Cheeto. Evenings tend to land at Burley Oak Brewing Company, a local fixture since 2009, with a beer garden, weekend music, and food trucks. The Inn Berlin, a five-room Victorian on an acre and a half, runs a gluten-free kitchen and a garden-sourced breakfast.
St. Michaels
St. Michaels runs on the water. The Inn at Perry Cabin sits along the Miles River with a restaurant, a pub pouring Choptank oysters, a spa, and a Pete Dye golf course. A ten-minute walk away is the Chesapeake Bay Maritime Museum, an 18-acre campus on Navy Point with a floating fleet of historic boats and a working shipyard where crews still restore Bay vessels by hand. Climb the 1879 Hooper Strait Lighthouse for a view over the river and the museum grounds. The Crab Claw, open March through November, keeps it simple with steamed blue crabs and a water view. Up Talbot Street, Lyon Distilling runs tastings and tours of its rum and whiskey operation.
Chestertown
Chestertown was listed on the National Register of Historic Places and designated a National Historic Landmark in 1970, and is held to be the best-preserved colonial seaport in the Mid-Atlantic. The centerpiece is the Schooner Sultana, a full-scale 1768 replica built right here between 1997 and 2001. Weekend sails leave the historic waterfront from April through mid-November, and passengers help raise the sails, take the seven-foot tiller, and haul a net to see what lives in the Chester River. A few blocks inland, the Garfield Center for the Arts at the Prince Theatre runs plays, concerts, comedy, and classic films in a restored 1920s house. On Saturdays, the Chestertown Farmers and Artisans Market fills Fountain Park with produce, bread, and handmade goods. Two miles out, the Brampton 1860 Inn trades the brick sidewalks for 35 acres of gardens and woods.
Oxford
Oxford has more boats than people. The best way in is the Oxford-Bellevue Ferry, widely called the oldest privately operated ferry in the country, crossing the Tred Avon since 1683. Once ashore, the Oxford Museum covers three centuries of local history through photographs, shipbuilding pieces, and family heirlooms. Next door, Scottish Highland Creamery handcrafts more than 700 ice cream flavors in rotation and scoops about 20 a day, from Old Bay with potato chips to double Belgian chocolate. Take a cone to the park bench across the street and watch the river. Down the Strand, Doc's Sunset Grille faces west over the Tred Avon for seafood and crab cakes, and Sandaway Suites and Beach has its own small sandy beach and Adirondack chairs at the water.
Leonardtown
Leonardtown calls itself the only Arts and Entertainment District in Southern Maryland, and the square stays busy year-round. Shepherd's Old Field Market is the signature stop, a former 1900s hardware warehouse turned into a 9,000-square-foot marketplace with more than 90 local vendors, a beer garden, and a coffee shop. Browsing the antiques and handmade goods can fill an afternoon. Ten minutes south, Leonardtown Wharf Park opens onto Breton Bay, where you can rent a kayak to paddle McIntosh Run or walk the boardwalk past the docks. The Inn at Leonardtown puts you within walking distance of the square. Three miles west, the Port of Leonardtown Winery makes award-winning wines entirely from Maryland grapes, with weekend music on the pavilion.
Solomons
Solomons sits where the Patuxent River meets the Chesapeake Bay, which makes it an easy base for a weekend on the water. Start at the Calvert Marine Museum, where the waterfront campus covers paleontology, estuary ecology, and Bay maritime history. Tour the restored 1883 Drum Point Lighthouse, one of only three surviving screwpile lighthouses on the Bay, then watch the resident otters Bubbles and Squeak before looking at fossils pulled from the Calvert Cliffs that date back roughly 20 million years. From there it is a short walk onto the Solomons Island Boardwalk, with views across the Patuxent toward the Governor Thomas Johnson Bridge. The Solomons Victorian Inn, in a restored 1906 home, keeps wraparound porches and harbor views. A short drive away, the 30-acre Annmarie Sculpture Garden shows works on loan from the Smithsonian and the National Gallery of Art.
Oakland
Oakland holds down Maryland's mountain corner. Nine miles north of downtown, Swallow Falls State Park runs the 1.5-mile Canyon Loop Trail through one of the state's last old-growth hemlock forests to four waterfalls, including the 53-foot Muddy Creek Falls, the highest free-falling waterfall in Maryland. You can stand on the spot where Henry Ford, Thomas Edison, and Harvey Firestone camped in 1921. Four miles south, Herrington Manor State Park centers on a 53-acre mountain lake good for kayaking, fishing, and a swim off the sandy beach. On the way back to town, Alpaca Acres Farm and Fun runs guided alpaca walks and a farm store. The Oak Mar Motel sits in the middle of downtown, with most of the attractions inside 15 minutes.
Cumberland
Cumberland was the Gateway to the West long before it became a trail town, and the two ideas fit together well. The restored 1913 station of the Western Maryland Scenic Railroad sends vintage cars on a 32-mile round trip to Frostburg behind steam locomotive No. 1309, climbing through the Allegheny Mountains and the 914-foot Brush Tunnel before a 90-minute stop in Frostburg. The station is also Mile Zero of the Great Allegheny Passage, the 150-mile trail to Pittsburgh, where it meets the 184.5-mile C&O Canal Towpath that follows the Potomac River toward Washington. Rent a bike or walk a short stretch to get the feel without the full route. Downtown, the Ferleman Gallery pairs art with live music, and the C. William Gilchrist Gallery occupies an 1845 Federal mansion with six gallery spaces. The Inn on Decatur handles the overnight in an 1800s building.
Thurmont
Thurmont sits at the base of the Catoctin Mountains, about 70 miles from Baltimore, with two parks doing most of the work. Three miles out on Route 77, Cunningham Falls State Park runs a short boardwalk trail to the 78-foot Cunningham Falls, the tallest cascading waterfall in the state, plus the 43-acre Hunting Creek Lake for swimming and trout fishing. Across the road, Catoctin Mountain Park protects 5,770 acres and 25 miles of trail, including the 3.9-mile Wolf Rock and Chimney Rock Loop and the shorter Blue Blazes Whiskey Still Trail to a rebuilt Prohibition-era still. In fall, Catoctin Mountain Orchard opens more than a dozen apple varieties for picking, with wagon rides, a market, and a bakery known for cider doughnuts. The Ole Mink Farm Recreation Resort rents log cabins in the mountains, many with fireplaces and hot tubs.
Ocean City
Ocean City is a 10-mile barrier island Maryland has come back to for over a century. Ocean City Beach has free public access the length of the island, so a spot on the sand is easy to claim. Swim in the Atlantic, rent an umbrella for the day, or come early for the sunrise, and in summer the beach runs free fireworks, movies, and yoga. From there, step onto the three-mile Ocean City Boardwalk, open since 1910, where Thrasher's French Fries has sold buckets of fries with vinegar since 1929. Trimper's Rides, running since 1893, is the nation's longest continuously family-owned amusement park and keeps a restored 1912 Herschell-Spillman carousel. The Castle in the Sand Hotel, a family-owned beachfront spot near the boardwalk, keeps direct beach access and an oceanfront pool.
A Weekend Is All It Takes
Maryland does not ask much of a weekend. Oxford scoops ice cream steps from a river you cross by ferry, and Thurmont puts the state's tallest cascading waterfall a half-mile from the parking lot. The state runs the Allegheny Mountains in the west, barrier-island beaches on the Atlantic coast, and the Chesapeake Bay and its Eastern Shore in between. Whatever pace you want, these ten towns make it easy to slow the clock and still come home with stories.
