Ready to trade your winter blues for a plate of blue crabs? As the Philly frost melts into warmer days, spring is the perfect season to hit the road and explore the diverse landscapes and deep-rooted history just a few hours south in Maryland.
Often called “America in Miniature,” Maryland packs a stunning variety of scenes and scenery into its borders. Seagrass dunes line the east, oak forests roll through the Piedmont, and pine-covered mountains rise in the west. Bald cypress trees tower over Chesapeake marshes, harbor towns bustle with fresh seafood, and historic landmarks whisper stories of the past.
Whether you’re a history buff, nature lover, or foodie, Maryland offers something for every flavor of fun.
So, what’s the plan? Maryland’s hidden gems each deserve their own weekend getaway, but with close proximity and endless variety, you can easily mix and match to craft your own adventure: Catch a live performance in Howard County, sip your way through the Craft Beverage Trail of St. Mary’s County, or hunt for prehistoric fossils along the cliffs of Calvert County. With waterfront strolls, sunset cruises, historic plantations, and lively arts districts, this spectacular region is brimming with beauty and excitement.
No matter which county you choose — or if you visit all three — Maryland’s spring delights are calling. Here’s your county-by-county guide to a weekend you’ll never forget.
Art meets heart in Howard County
Just two hours from Philadelphia, Howard County sits just minutes between Baltimore and Washington, D.C., offering a seamless blend of culture, history, and charm. With a thriving arts scene, dynamic downtowns, historic Main Streets, and scenic green spaces, it’s an excellent place to start your Maryland experience.
Escape to lakeside luxury at Merriweather Lakehouse
Step into a world of lakeside charm at the Merriweather Lakehouse Hotel, where sleek, modern design meets serene beauty. Nestled along the calm waters of Lake Kittamaqundi, this 212-room boutique hotel offers a peaceful retreat just a short drive from home. Unwind in spa-inspired guest rooms, savor delicious meals at the on-site restaurant, and bask in the tranquility by the rooftop pool. It’s the ideal setting to recharge before your Howard County adventure unfolds.
Sip and savor the Merriweather District
Spend your morning wandering through the Merriweather District, a vibrant area full of public art, gardens, and boutique services. Grab a coffee from a local café and bask in the mix of natural beauty and modern charm.
Dinner theatre at Toby’s
For a unique experience, enjoy a dinner-and-theater night at Toby’s Dinner Theatre. The rotating Broadway-style performances and delicious meals offer an entertaining way to spend the evening.
Brunch in Ellicott City
On Sunday, head to historic Ellicott City for a leisurely brunch. Explore 18th-century streets lined with antique stores, art galleries, and family-owned shops. Grab a mimosa and enjoy the charming atmosphere before savoring your meal at one of the cozy local spots.
Where to next?
Once you’ve dipped your toes into Howard County’s artsy charm — whether you’ve shopped, spa’d, or belted out Broadway tunes — you’re ready to dive deeper into Maryland’s rich history. Head south to St. Mary’s County, just 90 minutes away, where colonial landmarks, scenic shorelines, and a robust craft beverage scene await, offering an inspiring mix of old-world charm and new-world flavor.
Sippin’ and sailin’ in St. Mary’s County
Start things off at Maryland’s first capital — Historic St. Mary’s City. This living history museum transports visitors to the 17th century with reconstructed buildings, costumed interpreters, and interactive exhibits. Climb aboard Maryland Dove, a replica of the 1634 ship that carried settlers to these shores, and watch artisans practice traditional crafts like hide tanning and hearth cooking.
Sip your way along the Craft Beverage Trail
Raise a glass to local flavors on the St. Mary’s Craft Beverage Trail, a self-guided journey through 13 craft producers offering everything from locally roasted coffee and small-batch spirits to beer, wine and farm-fresh juices. Whether you’re in the mood for a crisp cider, a smooth bourbon, or a bold espresso, this trail is a toast to shared experiences and regional craftsmanship.
Stroll through Leonardtown
Leonardtown, once dubbed “a most convenient place” in the 18th century, lives up to its name as a walkable hub of dining, shopping, and entertainment. Start at the Visitor Center, housed in the Old Jail Museum (a National Part Service Underground Railroad Network to Freedom site), for insider tips on must-see spots. Browse local boutiques, indulge in award-winning wines at a nearby vineyard, or take in the waterfront views from the town’s public pier. If you’re staying overnight, the recently renovated Inn at Leonardtown puts you steps away from all the action.
Get a deeper look at history at Sotterley
At Historic Sotterley, a National Historic Landmark and UNESCO Site of Memory for the Routes of Enslaved Peoples, history speaks through the land itself. Tour the 18th-century Manor House, then walk down to the 1830s Slave Cabin exhibit for a powerful perspective on the lives of the enslaved individuals who lived and worked here. The “Land, Lives and Labor” exhibit, housed in the historic Corn Crib, features oral histories, interactive displays, and artifacts that tell the complex story of Sotterley’s past.
Love being out on the water?
Aye aye, Captain! Fish the Bay Charters has exactly what you need: fishing charters, sunset cruises, lighthouse excursions, Waterman Heritage tours, and more. Captain Phil, a certified Chesapeake Bay Storyteller, will introduce you to the beauty, heritage, and delicate balance of the region’s estuaries as you tour the same waterways as Captain John Smith and the first settlers of Maryland. Then, along the shore, visit Piney Point Lighthouse Museum & Historic Park, home to the oldest lighthouse on the Potomac River. Climb the tower for sweeping river views, tour the keeper’s quarters, or explore the maritime museum, which houses six historic wooden boats.
After soaking in St. Mary’s County’s coastal charm, continue your journey to Calvert County, where towering cliffs and cracking crab claws await.
Cliffs and Chesapeake breezes in Calvert County
Ready to unearth the past? Your adventure begins with a hike at Calvert Cliffs State Park, where towering cliffs reveal fossils from 10–20 million years ago. Search for prehistoric shark teeth along the sandy shore or explore the park’s trails and playground.
Dive into history at the Calvert Marine Museum
At the Calvert Marine Museum, history, marine life, and paleontology come together to tell the Chesapeake Bay’s story. Wander through exhibits featuring live animals, fossils, and interactive displays. Walk the Marsh Boardwalk, a prime birding spot, or visit the Paleontology Exhibit, where you can marvel at ancient remains of whales, sharks, and seabirds.
Explore art and nature at Annmarie Sculpture Garden & Arts Center
For a creative escape, visit Annmarie Sculpture Garden & Arts Center, where wooded paths wind past sculptures — including pieces on loan from the Smithsonian. This vibrant arts hub hosts seasonal events like Artsfest and Annmarie Garden in Lights, along with year-round workshops and markets.
Walk among ancient trees at Battle Creek Cypress Swamp
Step into the Battle Creek Cypress Swamp, one of North America’s northernmost bald cypress stands. A scenic boardwalk trail leads through this rare wetland habitat, where migrating warblers and red-eyed vireos add to the natural beauty.
Discover 9,000 years of history at Jefferson Patterson Park
History buffs can also explore Jefferson Patterson Park, a 560-acre site along the Patuxent River with over 65 archaeological sites. Visit the Maryland Archaeological Conservation Laboratory (MAC Lab), home to 8 million artifacts, or hike scenic trails with stunning river views.
Crackin’ claws in Calvert County
Who’s hungry? Calvert County is a seafood lover’s dream, offering the freshest crabs, oysters, and soft-shells from the Chesapeake Bay. After a long day, indulge in a crab feast at local spots like the Abner’s Crabhouse or Coast 2 Coast Seafood Bar & Grill, where the flavors of the Bay take center stage with every bite.
A Maryland weekend to remember
Alright, Philly, don’t you think it’s time to stow your winter coat, embrace the changing seasons, and channel the Eagles’ winning spirit into a well-earned weekend victory lap? Agreed! Just a short drive away, escape to Maryland’s unique blend of history, nature, and local flavor — Your unforgettable weekend awaits!
Visit the Howard County, St. Mary’s County, and Calvert County websites for more information.