2-Day Itineraries in Maryland

Weekend getaways with every day mapped out — verified attractions, realistic pacing.

35 itineraries

Salt Air & Wild Shores: A Solo Escape to Ocean City

2 Days · Solo

Ocean City area, Maryland

Salt Air & Wild Shores: A Solo Escape to Ocean City

4 stops

Mill Wheels & Wildflowers: A Solo Wander Through Patapsco Valley

2 Days · Solo

Patapsco Valley (Ellicott City, Sykesville), Maryland

Mill Wheels & Wildflowers: A Solo Wander Through Patapsco Valley

5 stops

Boardwalk Lights & Wild Shores: 2 Days in Ocean City

2 Days · Teen Families

Ocean City area, Maryland

Boardwalk Lights & Wild Shores: 2 Days in Ocean City

4 stops

Salt Air & Wild Horses: A Solo Weekend in Ocean City

2 Days · Solo

Ocean City area, Maryland

Salt Air & Wild Horses: A Solo Weekend in Ocean City

4 stops

Mill Town Light & River Trails: 2 Days in Patapsco Valley

2 Days · Teen Families

Patapsco Valley (Ellicott City, Sykesville), Maryland

Mill Town Light & River Trails: 2 Days in Patapsco Valley

5 stops

Mill Wheels & Wildflowers: Two Easy Days in the Patapsco Valley

2 Days · Active Retirees

Patapsco Valley (Ellicott City, Sykesville), Maryland

Mill Wheels & Wildflowers: Two Easy Days in the Patapsco Valley

3 stops

Salt Air & Sand Dollars: A Gentle Two Days in Ocean City

2 Days · Active Retirees

Ocean City area, Maryland

Salt Air & Sand Dollars: A Gentle Two Days in Ocean City

4 stops

Waterlight and Wide Skies: Two Days on Maryland's Eastern Shore

2 Days · Active Retirees

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Waterlight and Wide Skies: Two Days on Maryland's Eastern Shore

4 stops

Millstones & Main Street: Two Autumn Days in the Patapsco Valley

2 Days · Active Retirees

Patapsco Valley (Ellicott City, Sykesville), Maryland

Millstones & Main Street: Two Autumn Days in the Patapsco Valley

6 stops

Brick, Bay, and Quiet Water: Two Days in Annapolis

2 Days · Active Retirees

Annapolis area, Maryland

Brick, Bay, and Quiet Water: Two Days in Annapolis

4 stops

Mill Light & River Song: Two Days in the Patapsco Valley

2 Days · Couples

Patapsco Valley (Ellicott City, Sykesville), Maryland

Mill Light & River Song: Two Days in the Patapsco Valley

6 stops

Cobblestones and Cascades: A Family Weekend in the Patapsco Valley

2 Days · Young Families

Patapsco Valley (Ellicott City, Sykesville), Maryland

Cobblestones and Cascades: A Family Weekend in the Patapsco Valley

3 stops

Cobblestones & Cascades: A Family Weekend in the Patapsco Valley

2 Days · Young Families

Patapsco Valley (Ellicott City, Sykesville), Maryland

Cobblestones & Cascades: A Family Weekend in the Patapsco Valley

4 stops

Waterlight & Wild Marsh: A Two-Day Eastern Shore Escape

2 Days · Couples

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Waterlight & Wild Marsh: A Two-Day Eastern Shore Escape

5 stops

Sailboats, Storybook Streets & Salt Air: 2 Days in Annapolis with Little Ones

2 Days · Young Families

Annapolis area, Maryland

Sailboats, Storybook Streets & Salt Air: 2 Days in Annapolis with Little Ones

4 stops

Splash Pools & Star-Spangled Skies: A Family Weekend in Baltimore

2 Days · Young Families

Baltimore area, Maryland

Splash Pools & Star-Spangled Skies: A Family Weekend in Baltimore

4 stops

Mill Light & River Song: A Fall Escape to the Patapsco Valley

2 Days · Couples

Patapsco Valley (Ellicott City, Sykesville), Maryland

Mill Light & River Song: A Fall Escape to the Patapsco Valley

4 stops

Harbor Light & Fort Walls: A Baltimore Weekend for Two

2 Days · Couples

Baltimore area, Maryland

Harbor Light & Fort Walls: A Baltimore Weekend for Two

7 stops

Wooden Boats & Wide-Open Marshes: A Family Weekend on Maryland's Eastern Shore

2 Days · Young Families

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Wooden Boats & Wide-Open Marshes: A Family Weekend on Maryland's Eastern Shore

3 stops

Brick, Bay, and Sailboat Light: Two Days in Annapolis

2 Days · Couples

Annapolis area, Maryland

Brick, Bay, and Sailboat Light: Two Days in Annapolis

5 stops

Sailboats, Statehouses & Sandy Toes: A Family Weekend in Annapolis

2 Days · Young Families

Annapolis area, Maryland

Sailboats, Statehouses & Sandy Toes: A Family Weekend in Annapolis

4 stops

Splash, Sail, and Stroll: A Gentle Baltimore Harbor Weekend for Little Ones

2 Days · Young Families

Baltimore area, Maryland

Splash, Sail, and Stroll: A Gentle Baltimore Harbor Weekend for Little Ones

3 stops

Harbor Light & Cobblestone Nights: Two Days in Baltimore

2 Days · Couples

Baltimore area, Maryland

Harbor Light & Cobblestone Nights: Two Days in Baltimore

7 stops

Marsh Light & Harbor Nights: A Two-Day Eastern Shore Escape

2 Days · Couples

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Marsh Light & Harbor Nights: A Two-Day Eastern Shore Escape

6 stops

Wooden Boats & Marsh Light: A Family Weekend on Maryland's Eastern Shore

2 Days · Young Families

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Wooden Boats & Marsh Light: A Family Weekend on Maryland's Eastern Shore

4 stops

Brick, Sail & Marsh Light: Two Days in Annapolis

2 Days · Couples

Annapolis area, Maryland

Brick, Sail & Marsh Light: Two Days in Annapolis

5 stops

Salt Air & Slow Mornings: Two Days Along Ocean City's Shore

2 Days · Active Retirees

Ocean City area, Maryland

Salt Air & Slow Mornings: Two Days Along Ocean City's Shore

3 stops

Salt Air & Wild Horses: A Couples' Escape to Ocean City

2 Days · Couples

Ocean City area, Maryland

Salt Air & Wild Horses: A Couples' Escape to Ocean City

4 stops

Salt Air & Small Steps: A Family Weekend in Ocean City

2 Days · Young Families

Ocean City area, Maryland

Salt Air & Small Steps: A Family Weekend in Ocean City

3 stops

Boardwalk Nights & Wild Horse Mornings: 2 Days in Ocean City

2 Days · Teen Families

Ocean City area, Maryland

Boardwalk Nights & Wild Horse Mornings: 2 Days in Ocean City

4 stops

Salt Air & Wild Shores: A Couples' Escape to Ocean City

2 Days · Couples

Ocean City area, Maryland

Salt Air & Wild Shores: A Couples' Escape to Ocean City

4 stops

Sandcastles & Sea Ponies: Two Easy Days in Ocean City

2 Days · Young Families

Ocean City area, Maryland

Sandcastles & Sea Ponies: Two Easy Days in Ocean City

3 stops

Millstone & Mist: A Solo Fall Wander Through the Patapsco Valley

2 Days · Solo

Patapsco Valley (Ellicott City, Sykesville), Maryland

Millstone & Mist: A Solo Fall Wander Through the Patapsco Valley

6 stops

Brick, Bay, and Solitude: Two Days in Annapolis

2 Days · Solo

Annapolis area, Maryland

Brick, Bay, and Solitude: Two Days in Annapolis

5 stops

Marsh Light & Harbor Quiet: Two Days Alone on Maryland's Eastern Shore

2 Days · Solo

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Marsh Light & Harbor Quiet: Two Days Alone on Maryland's Eastern Shore

6 stops

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