7-Day Maryland Itinerary

A mix of historic sites, scenic coastal drives, outdoor adventures, and world-famous seafood across Maryland.

The Ultimate Maryland Family Vacation: Kid-Friendly Adventures, Beaches & History

Day1

Arrive in Baltimore & Explore

Fly into Baltimore/Washington International Thurgood Marshall Airport (BWI).

Top Things to Do in Baltimore

  • Visit the Inner HarborHome to the National Aquarium & historic ships.
  • Tour Fort McHenry National MonumentThe birthplace of the Star-Spangled Banner.
  • Catch an Orioles Game at Camden Yards (Seasonal).
  • Try Local Craft Beer at Heavy Seas or Union Craft Brewing.
  • Dinner at Nick's Fish House or LP SteamersEnjoy Maryland blue crabs!

Overnight in Baltimore.

Day2

Annapolis - Maryland's Capital & Sailing City

Drive from Baltimore to Annapolis (45 min).

Top Things to Do in Annapolis

  • Tour the Maryland State HouseThe oldest state capitol still in use.
  • Visit the U.S. Naval AcademyWalk through this historic military campus.
  • Take a Sailing Cruise on the Chesapeake Bay.
  • Try Crab Cakes at Cantler's Riverside Inn.

Overnight in Annapolis.

Day3

Chesapeake Bay & St. Michaels

Drive from Annapolis to St. Michaels (1 hour).

Top Things to Do in St. Michaels

  • Visit the Chesapeake Bay Maritime Museum.
  • Go Kayaking on the Miles River.
  • Wine Tasting at St. Michaels Winery.
  • Dinner at The Crab ClawA classic waterfront seafood spot.

Overnight in St. Michaels or nearby Easton.

Day4

Assateague Island & Ocean City Beach Day

Drive from St. Michaels to Assateague Island (2 hours).

Top Things to Do at Assateague Island National Seashore

  • See the Wild Ponies Roaming the Beach.
  • Relax on the White Sand Beaches.
  • Bike Along the Scenic Island Trails.

Top Things to Do in Ocean City

  • Walk the Ocean City BoardwalkOne of the best on the East Coast.
  • Try Thrasher's French Fries & Dumser's Dairyland Ice Cream.
  • Ride Amusement Park Rides at Trimper's (Seasonal).

Drive to Ocean City, MD (30 min).

Overnight in Ocean City.

Day5

Deep Creek Lake & Western Maryland

Drive from Ocean City to Deep Creek Lake (4.5 hours).

Top Things to Do at Deep Creek Lake

  • Rent a Boat or Go Kayaking on the Lake.
  • Hike at Swallow Falls State ParkSee Maryland's tallest waterfall!
  • Skiing & Snow Activities (Winter Only) at Wisp Resort.
  • Dinner at Mountain State Brewing Co.

Overnight in Deep Creek Lake.

Day6

Antietam Battlefield & Harpers Ferry

Drive from Deep Creek Lake to Antietam National Battlefield (2 hours).

Top Things to Do at Antietam

  • Tour Antietam National BattlefieldSite of the bloodiest battle of the Civil War.
  • Walk the Sunken Road ("Bloody Lane").

Top Things to Do in Harpers Ferry

  • Hike Maryland Heights TrailAmazing views of the Potomac River.
  • Explore the Historic Town & John Brown's Fort.

Drive from Antietam to Harpers Ferry, WV (30 min).

Overnight in Frederick, MD.

Day7

Frederick & Return to Baltimore

Explore Frederick before heading back to Baltimore (1 hour).

Top Things to Do in Frederick

  • Walk Through the Historic Downtown.
  • Visit a Craft Brewery Like Flying Dog Brewery.
  • Explore Catoctin Mountain Park (Optional Stop).

Drive to BWI Airport (1 hour) & Depart.

Fly home from Baltimore.

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Header photo: Don Ramey Logan, CC BY 4.0, via Wikimedia Commons.