Build-Your-Own Maryland Adventure

Day 1: Cumberland

Walk, run or bike the Chesapeake & Ohio Canal towpath looking for locks and lockhouses along the Potomac River. Nearby Rocky Gap State Park’s rhododendron- and mountain-laurel-lined trails complement the sapphire waters of Lake Habeeb, perfect for fishing, boating and swimming. Tuck in for the night at Frostburg’s Allegheny Trail House, a historical bed and breakfast geared toward bike enthusiasts.

• Corner Tavern & Cafe: Bacon paninis, avocado toast & bagel sandwiches
• All that 2go & Bakery!: Fried fish, dirty rice & Southern delights
• Crabby Pig: Regional classics from lump crab cakes to smoked pork ribs 

Day 2: Thurmont

Catoctin Mountain Park’s Chimney Rock and Hog Rock hikes are calf-burners that reward with vistas of the Appalachians’ dense greenery. Let the interpretive signs of the Catoctin Furnace African American Cemetery & Trail guide you through the past and the roles of enslaved African-American ironworkers in building the industrial might of our nation.Blue Ridge Mountain scenery pairs perfectly with reds, whites and rosés at Catoctin Breeze and Links Bridge vineyards. Call it a night at family-owned Ole Mink Farm Recreation Resort, where luxury log cabins, hot tubs and firepits welcome you.

• Thurmont Kountry Kitchen: Country-fried steak, pancakes and to-go whoopie pies
• The Farmhouse Exchange: Fresh sandwiches & deli fare
• The Carriage House Inn, Emmitsburg: Upscale faves, like crab dip, local seafood and prime rib 

Day 3: Frederick

Cast for channel catfish and smallmouth bass on the Monocacy River. This leg of Maryland’s Fly Fishing Trail delights with serene waters, tree-shaded banks and old-fashioned structures like stone bridges. Earn some hiker bragging rights by bagging a section of the Appalachian Trail via Greenbrier State Park. Victorian-era stylings make excellent fodder for sweet dreams at Hollerstown Hill Bed and Breakfast.

• Cafe Nola: Shrimp and grits & vegan breakfast sandwiches
• Lazy Fish: Artisanal sushi
• Isabella's Taverna & Tapas Bar: Small plates & paella

Shopping Side Trips

Stroll the ornate historical storefronts of downtown Cumberland and Frederick for antiques, boutique fashions, toys and local artwork.

Wellspring Manor & Spa, Upper Marlboro

Utter indulgence is the name of this cheery, red-brick manor’s game. You’ll be greeted by welcoming hosts, plush robes, daily hors d'oeuvres service and an on-site art gallery with a resident curator. Stroll the property’s seven serene acres, meditate by the pool or book treatments at the exclusive, guest-only spa. Check out package deals for perks like Champagne, wellness journals, VIP event tickets and cultural celebrations.

More to explore nearby: Darnall's Chance House Museum • Two Lions Vineyards • Merkle Wildlife Sanctuary

Inn at Perry Cabin, St. Michaels

A stay at this early-1800s Colonial-style riverfront inn takes you out of reality and into a vacation storybook. Kick back on your private terrace or balcony and luxuriate in coastal moonlight and the aromas of garden herbs (used in the inn’s kitchen and spa treatments). Three on-site restaurants, a spa, a golf course, yoga and lawn games mean you’ll never have to leave, but the inn can also arrange for boating and paddling trips.

More to explore nearby: Hooper Strait Lighthouse • LYON RUM // Windon Distilling Company • Chesapeake Bay Maritime Museum

Shopping Side Trip

Bike into St. Michaels to look for nautically themed souvenirs, sample high-end olive oils and soak up small-town vibes.

Elk Forge B & B Inn, Spa & Events, Elkton

Set snug amid nature trails and rose gardens, this historical property offers everything a modern-day traveler needs to escape and unwind. Rooms and suites pamper you with cozy robes, Victorian soaking tubs, fireplaces and elegant wood furnishings. The Tea Garden Spa ups the relaxation ante with a robust menu of facials, massages and mineral-rich body scrubs.

More to explore nearby: Patriots Glen National Golf Club • Gilpin's Falls covered bridge and hike • Milburn Orchards

Days 1 & 2: Deep Creek Lake State Park

This beloved recreation area has so much to offer, you could spend a week here. Hit the swim beach before drying off on 20 miles of trails or speed things up with boat or Jet Ski rentals. Nearby Funland earns its name with bumper cars, go karts and water-balloon wars, while Adventure Sports Center International boasts the world’s only mountaintop recirculating white-water course. Or take to the air via obstacle and ropes courses at Monkey Business Adventure Park. Sleep under the stars at Deep Creek Lake campsites or at Ella’s Enchanted Treehouses, which offers up-high lodging for everyone thanks to their wheelchair-accessible DayDreamer treehouse.

• Glazed & Confuzed Donuts Gone Wild: Cake doughnuts with funky flavors
• Archie's Barbeque: Brisket, smoked wings & cornbread
• Honi-Honi Bar: Family-friendly watering hole with pub grub & live music 

Day 3: Adventure on the Road

At Hagerstown’s Discovery Station, work off car-ride energy exploring two floors of hands-on STEAM exhibits ranging from dinosaurs to LEGO robotics. Plan your second leg-stretch for Irvine Nature Center in Owings Mills: Snap pics of your starry-eyed littles in the butterfly house, learn about Native American life and meet the resident raptors. Perryville’s your snooze spot tonight, where a cabin-esque suite at Great Wolf Lodge awaits.

• The Filling Station, La Vale: Eggs, biscuits & breakfast classics
• The Dog House, Hagerstown: Zany hot dogs, brats & burgers
• Mari Luna, Pikesville: Tacos, pupusas & nachos

Day 4: Great Wolf Lodge

Take a break from the road and spend a day (or three) living it up at this water-park extravaganza. Drift on the lazy river, race down tubes and slides, sink baskets from a wave pool or soak in the hot springs. Un-prune your fingers playing arcade games, bowling, mini-golfing and more. And with eight on-site dining options, you’ll have no trouble wrangling meals.

Day 5: Six Flags America

Our largest amusement park is a mere 90-minute drive from Great Wolf Lodge — just enough time to get the fam pumped. Choose from 100-plus rides, whether you want to be dipped and flipped on eight roller coasters or prefer low-key carousel spins. The park is loaded with places to grab a bite, and you’ll also find plenty of shows and special events. Crash for the night at one of many classic hotels in Bowie.

Day 1: Germantown & Sandy Spring

Maryland celebrates the people that make it special, and the Button Farm Living History Center is a prime example of how we honor our past. Learn about the lives of enslaved Black Americans and 19th-century agriculture via living-history exhibits. At Woodlawn Museum and Sandy Spring Slave Museum, exhibits, an Underground Railroad Experience Trail and an art gallery shed light on the lives of African Americans, their quest for freedom and the Civil Rights Movement.

• MoCo Nutrition: Protein shakes, smoothies & energy teas
• The Caribbean Flavor: Beef patties, saltfish & coco bread
• Mansa Kunda Restaurant: Authentic West African fare 

Day 2: Ellicott City

Chug over to the wee Baltimore & Ohio Ellicott City Station Museum — America’s oldest surviving depot — for artifacts, station rooms, a caboose and an impressive model train. At Howard County Center of African American Culture, immerse yourself in local Black history via vintage clothing and displays. Bunk down at The Wayside Inn, an 18th-century spot that (maybe) gave shelter to George Washington and John Quincy Adams.

• Old Mill Cafe: Crepes & bagels with lox
• Choose from many options along Korean Way, like Kim Bob Na Ra or Honey Pig Restaurant
• Tigi's Ethiopian Restaurant & Market: Ethiopian classics with lots of vegan options 

Shopping Side Trips

In Ellicott City and across St. Mary’s County, find shops in old-timey and cheerfully painted historical buildings selling everything from alpaca-wool clothing to used books.

Day 3: St. Mary’s County

A dedicated site along UNESCO’s Routes of Enslaved Peoples, Hollywood’s Historic Sotterley doesn’t sugarcoat the past. The board of trustees includes descendants of the enslaved Black Americans who worked the plantation, which uses its 20 historical structures and educational programs as a “testament to all who lived, died, labored and resisted here.” At the Old Jail Museum in Leonardtown, an Underground Railroad Network to Freedom site, discover the stories of freedom seekers who were held captive. Absorb what you’ve learned as you look out over the water at Ridge’s Swanendele Inn.

• Stirred, Hollywood: Cinnamon rolls & shrimp and grits
• The Jamaican Grill, California: Caribbean takeout, like jerk chicken
• Uncle D's Grill, Lexington Park: Southern-style barbecue & fish 

Day 4: Vienna

The Nanticoke River holds so much history, it’s a wonder it doesn’t spill its banks. In fact, the name means “tidewater” in Algonquin, the language of the Nanticoke people. Learn about the waterway, traveled by Harriet Tubman and John Smith, at the Nanticoke River Discovery Center. Then, paddle past paw paws and sassafras while looking for bald eagles on the Nanticoke Water Trail, knowing you’re on routes similar to those traveled by Harriet Tubman and John Smith. Keep the outdoorsy theme going with a stay at Roaring Point Waterfront Campground, where DJs, games and swimming await.

• Swanendele Inn: Complimentary with your stay
• Millie's Road House Bar: Crab cakes, burgers & friendly vibes
• Boonies Burgers, Beer & Bait: Regional specialties, like rockfish & crab 

Check out our byways road trips for more Maryland history.

Days 1 & 2: Baltimore

In Graffiti Alley, artistic expression via spray paint is totally legal, creating an ever-changing exhibition. Take in the world’s largest Matisse collection — 1,200-plus pieces — along with the works of Picasso, Cézanne and van Gogh at the Baltimore Museum of Art. Stroll a collection spanning seven millennia at The Walters Art Museum, with highlights including ancient maps and Egyptian artifacts. Named for a Harlem Renaissance jazz great, the Eubie Blake National Jazz Institute and Cultural Center hosts African dance performances, workshops and local art exhibits. Come evening, take your pick of entertainment, with everything from indie bands to improv. The Creative Alliance, Hippodrome Theatre, Baltimore Symphony Orchestra, Chesapeake Shakespeare Company, Ottobar and Metro Gallery are just the tips of the performance iceberg. Tuck in for the night at Sagamore Pendry Baltimore, a swank hotel on the water in Fells Point that’s a work of art itself.

• Station North Arts Cafe Gallery: Artsy coffee shop fare
• Gertrude’s Chesapeake Kitchen: Vegan and regular crab cakes
• The Helmand: Authentic Afghan restaurant famous for its pumpkin appetizer 

Day 3: Wheaton & Bethesda

Wheaton and Bethesda Arts & Entertainment Districts are rich with inspiration and culture. Bethesda comes alive with public art, vibrant murals and a thriving gallery scene, while Wheaton’s events calendar is packed with cultural celebrations. You’ll also find the award-winning Brookside Gardens, where you can marvel at the artistry behind cultivated blooms. And in nearby Travilah, the contemporary Glenstone Museum stars the likes of Diane Arbus and Andy Warhol. Let your head hit luxe pillows at The Oaks Bed & Breakfast Inn, where fresh cookies, weekly yoga, and wine and cheese nights enhance the experience.

• Nick’s Diner, Wheaton: Banana pancakes and scrapple (spiced pork-scrap loaf)
• Cubano’s, Bethesda: Cuban classics including ham croquetas and slow-roasted pork
• Kuya Ja's Lechon Belly, Wheaton: Filipino dishes like pork belly and sweet spaghetti 

Day 3: Chestertown & Denton

Dip into Chestertown’s riverfront to peruse paintings, sculptures and jewelry in small-town galleries. The public arts scene is nothing to sneeze at either: Snap pics of bike-cog butterflies and metal waves protruding from mounds of grass. The Denton Artsway is another hidden gem — the tiny city center is packed to the gills with creator spaces showcasing fiber arts, pottery, notecards and collage. Let the day’s wanderings paint your dreams at Easton’s Hummingbird Inn — a charismatic Victorian that hosts mind-opening experiences like dinners in the dark.

• Cafe Xpress, Bethesda: Bagel sandwiches and Korean breakfast burritos
• Procolino's Pizza, Chestertown: New York-style pizza, subs and pasta
• Caroline’s, Denton: Eclectic farm-to-table fare, like sweet-potato pierogi and seared  snakehead 

Shopping Side Trip

The Avenue in Baltimore’s Hampden neighborhood is the place to browse quirky bookstores, boutiques and shops that sell both chic footwear and gourmet chocolate.
 
Explore all 29 Maryland Arts & Entertainment Districts.

Day 1: Annapolis

Maryland’s capital — and the Sailing Capital of America — is a water lover’s paradise. At Annapolis Maritime Museum & Park, find holographic watermen weaving tales, skipjack sailing tours and aquariums showing what 17th-century Chesapeake Bay was like. Head outside to admire the water via kayaks and SUPs or take a sunset cruise on the Schooner Woodwind. Stay at the naval-themed Graduate Annapolis to keep seafaring spirits high.

• Bread and Butter Kitchen: Welcoming vibes, scones and pancakes
• Chick & Ruth’s: Landmark known for crab cakes and milkshakes
• Carrol’s Creek Cafe: Fine dining with crab, oysters and waterfront views 

Day 2: Cambridge

Listen to your paddle slicing through the water’s surface at Blackwater National Wildlife Refuge. As you navigate your kayak or paddleboard through grassy thickets, watch for bushy-tailed Delmarva fox squirrels, musk beavers and a variety of ducks decked out in feathered finery. After, tour the Choptank River Lighthouse and its cozy maritime museum, taking time to soak up some of the best vistas for miles. Spend the night — or a week — at Hyatt Regency Chesapeake Bay Golf Resort, Spa And Marina for obvious reasons. (The name kind of says it all, right?)

• Iron Rooster, Annapolis: Crab Benedicts and Old Bay-rimmed bloody marys
• Bombay Social: Indian cuisine in a chill atmosphere
• Blue Ruin: Regionally themed cocktails and sophisticated mains 

Days 3 & 4: Ocean City

We could write a full book about what to do in Ocean City, but here are some highlights. Explore area history and surfing evolution at the Ocean City Life-Saving Station Museum before parasailing high above the Atlantic’s cresting waves. Spend a full day bouncing along the Ocean City Boardwalk. The early-1910s heartbeat of the town is also home to Jolly Roger’s exhilarating fair rides, a fishing pier, ice-cream parlors, bars, shops and locally loved Fisher’s Popcorn. Stay as close to the water as possible (without being in it) at Princess Royale Oceanfront Resort.

• Barn 34: Jalapeño-popper omelets and Cap’n Crunch French toast
• Blue Fish Restaurant & Bar: Sushi, boba and Asian favorites
• OCM Crabs: Beachside steamed seafood 

Shopping Side Trips

From vintage fashions and artisanal jewelry to seaside souvenirs, you’ll find no shortage of shops in Annapolis, Cambridge and Ocean City.