Havre de Grace · $$$$ — Top public
Road trips · Maryland
Maryland road trips & hidden gems.
Maryland packs Chesapeake Bay crab shacks, the sailing town of Annapolis, and Atlantic dunes at Assateague where wild horses roam the beach. Summer is bay season; fall turns crisp and quiet. Small state, big variety.
Best time to visitLate spring–fall
Don’t missWild horses on Assateague Island
Gem Hunt nominees10 candidates
Hikes10 curated
Worth-the-detour corridors
Drives through Maryland
Ranked city-to-city drives that cross Maryland — each with honest +N min detours on the shelf.
Gem Hunt nominees
What locals say you shouldn’t miss.
Community-nominated candidates. Add yours and vote to help choose the first published finalists.
Swallow Falls State Park
Maryland's tallest free-falling waterfall, the 53-foot Muddy Creek Falls, anchors a loop trail through old-growth hemlocks some over 300 years old, in the state's far-western mountains.
Antietam National BattlefieldOne of the most pristine and least crowded Civil War battlefields, with an 8.5-mile driving tour through rolling Sharpsburg farmland — quieter than Gettysburg and genuinely moving.
Ladew Topiary GardensTwenty-two acres of whimsical sculpted hedges, including a famous fox-and-hounds hunt frozen mid-chase across the lawn, in the horse country north of Baltimore.
Calvert Cliffs State ParkA 1.8-mile woodland trail leads to a Chesapeake beach where you can sift the sand for 10-to-20-million-year-old shark teeth and Miocene fossils, on southern Maryland's western shore.
Blackwater National Wildlife RefugeA four-mile Wildlife Drive winds through tidal marsh holding one of the East Coast's densest concentrations of nesting bald eagles, in a place locals call the Everglades of the North.
Smith IslandReachable only by boat from Crisfield, this remote Chesapeake island moves at a vanished pace across three tiny watermen's villages and is the birthplace of Maryland's ten-layer state cake.
Explore by interest
Everything else worth a stop in Maryland.
Start with a few highlights, choose one interest, or explicitly open the full state guide.
Showing General guide and Hikes highlights. Choose a category or Show all for the full state guide.
More worth the detour
The general guide to Maryland.
Museums, monuments, historic sites, and local-only stops from Roamward's shared place map.
American Visionary Art Museum
A national museum devoted entirely to self-taught 'outsider' artists -- whirligigs, a giant whirligig sculpture garden, and a mirrored mosaic facade that makes it the single quirkiest museum stop in the state.
B&O Railroad MuseumHoused in the 1884 Mount Clare roundhouse -- birthplace of American railroading, where the B&O's first stone was laid in 1828 -- with the country's oldest and most comprehensive collection of historic locomotives under one roof.
Bayard HouseCanal-view dining in an 1780s building at the foot of the bridge.
C&D Canal MuseumArmy Corps museum in the 1837 canal pumphouse with the original steam engines and waterwheel.
Calvert Marine Museum / Drum Point LighthouseOne of only three surviving Chesapeake Bay screw-pile 'cottage' lighthouses, moved intact to the museum's waterfront in 1975 -- visitors can climb inside a genuine 1883 hexagonal lighthouse without a boat.
Chesapeake Bay Maritime MuseumA working waterfront campus on the Miles River with the last screw-pile lighthouse on its original Bay waters (Hooper Strait Light, relocated intact) and the country's largest collection of Chesapeake Bay skipjacks and workboats.
Boots on
Best hikes in Maryland.
From family-easy to bucket-list — trails worth the detour, great for the RV & camping crew.
Annapolis Rock
a popular Appalachian Trail overlook
Billy Goat Trail (Potomac)a cliff-scramble along the Potomac gorge
Calvert Cliffsa beach of fossil-bearing cliffs on the bay
Cascade Falls (Patapsco)an easy forest loop to a pretty fall near Baltimore
Catoctin (Chimney + Wolf Rock)rock outcrops above Camp David country
Cunningham Fallsa cascade in the Catoctins
Where to wake up
Camping in Maryland.
The most scenic places to pitch a tent or park the rig — each with how to reserve and how RV-friendly it is.
Where to eat
Road-trip dining in Maryland.
Restaurants, diners, and food halls that fit the drive — curated by town, not scraped from a phone book.
Boatyard Bar & Grill
Award-winning Eastport sailors' hangout named best crab cake for two decades, with a raw bar and fish tacos.
Cantler's Riverside InnLegendary family-owned crab shack on Mill Creek, dumping dock-fresh steamed blue crabs onto brown-paper tables.
Carrol's Creek CafeWaterfront Eastport dining room and deck overlooking Spa Creek, a longtime special-occasion seafood favorite.
Lewnes' SteakhouseFamily-run Eastport chophouse open since 1921, an old-school special-occasion steakhouse with prime aged beef.
Rams Head TavernHistoric 1700s brick tavern pouring house-brewed beers alongside crab dip and pub classics.
The ChoptankEgo Alley fish and crab house in a prime waterfront spot centered on Chesapeake blue crabs, oysters, and rockfish.
On two wheels (road)
Best cycling in Maryland.
Scenic road rides, iconic climbs, and car-free rail-trails.
Sand & surf
Best beaches in Maryland.
Family sand, surf breaks, wild shores — find your vibe.
Chasing water
Best waterfalls in Maryland.
From roadside stops to bucket-list hikes — easy ones flagged for the RV & family crew.
Cunningham Falls
a cascading fall in the Catoctin Mountains, the tallest in Maryland.
Great Falls of the Potomaca dramatic series of cascades and rapids near D.C..
Muddy Creek FallsMaryland’s tallest free-falling fall, in Swallow Falls State Park.
Tolliver Fallsa small, picturesque fall near Swallow Falls in western Maryland.
Tee it up
Public golf you can book in Maryland.
Havre de Grace · $$$$ — Maryland's top public, ex-LPGA host
Ijamsville · $$$
Queenstown · $$$
Cambridge · $$$
Flintstone · $$$
Beacons
Lighthouses in Maryland.
Take me out
MLB ballparks in Maryland.
Plan the Maryland trip
Get the scenic route, the stops, and the timing.
Explore and save the trip on the web now. Join the iOS beta list for verified check-ins, shared trips, badges, and your growing map.
Where to stay
Find a place to stay near Maryland.
Hotels, cabins, and rentals close to the action — compare and book for your trip.
We may earn a commission from bookings made through this link — at no extra cost to you.