2 Days · Solo
Ocean City area, Maryland
Salt Air & Wild Shores: A Solo Escape to Ocean City
4 stops
2 Days · Solo
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Wheels & Wildflowers: A Solo Wander Through Patapsco Valley
5 stops
2 Days · Teen Families
Ocean City area, Maryland
Boardwalk Lights & Wild Shores: 2 Days in Ocean City
4 stops
2 Days · Solo
Ocean City area, Maryland
Salt Air & Wild Horses: A Solo Weekend in Ocean City
4 stops
2 Days · Teen Families
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Town Light & River Trails: 2 Days in Patapsco Valley
5 stops
2 Days · Active Retirees
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Wheels & Wildflowers: Two Easy Days in the Patapsco Valley
3 stops
3 Days · Solo
Ocean City area, Maryland
Salt Air & Wild Shores: 3 Days Solo in Ocean City
5 stops
3 Days · Solo
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Harbor Quiet: 3 Days Solo on Maryland's Eastern Shore
6 stops
3 Days · Solo
Patapsco Valley (Ellicott City, Sykesville), Maryland
River Light & Mill Stone: 3 Days in the Patapsco Valley
9 stops
2 Days · Active Retirees
Ocean City area, Maryland
Salt Air & Sand Dollars: A Gentle Two Days in Ocean City
4 stops
3 Days · Teen Families
Annapolis area, Maryland
Brick, Bay & Breeze: 3 Days in Annapolis for Teen Families
8 stops
2 Days · Active Retirees
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Waterlight and Wide Skies: Two Days on Maryland's Eastern Shore
4 stops
3 Days · Teen Families
Patapsco Valley (Ellicott City, Sykesville), Maryland
River Mist & Mill Stones: 3 Days in the Patapsco Valley
9 stops
3 Days · Teen Families
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Working Waterfronts: 3 Days on Maryland's Eastern Shore
6 stops
2 Days · Active Retirees
Patapsco Valley (Ellicott City, Sykesville), Maryland
Millstones & Main Street: Two Autumn Days in the Patapsco Valley
6 stops
2 Days · Active Retirees
Annapolis area, Maryland
Brick, Bay, and Quiet Water: Two Days in Annapolis
4 stops
3 Days · Solo
Annapolis area, Maryland
Brick, Bay, and Solitude: 3 Days in Annapolis
9 stops
3 Days · Teen Families
Baltimore area, Maryland
Harbor Light & Old Bay Nights: 3 Days in Baltimore
9 stops
3 Days · Solo
Annapolis area, Maryland
Brick, Bay, and Bell Towers: A Solo Autumn in Annapolis
6 stops
3 Days · Solo
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Harbor Quiet: 3 Days Solo on Maryland's Eastern Shore
6 stops
3 Days · Solo
Baltimore area, Maryland
Harbor Light, Fort Walls & Forest Falls: 3 Days Solo in Baltimore
10 stops
3 Days · Teen Families
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Wheels & Waterfalls: Three Fall Days in the Patapsco Valley
10 stops
3 Days · Teen Families
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Harbor Towns: 3 Days on Maryland's Eastern Shore
6 stops
3 Days · Teen Families
Annapolis area, Maryland
Brick, Bay & Breeze: A Teen Family Weekend in Annapolis
6 stops
2 Days · Couples
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Light & River Song: Two Days in the Patapsco Valley
6 stops
2 Days · Young Families
Patapsco Valley (Ellicott City, Sykesville), Maryland
Cobblestones and Cascades: A Family Weekend in the Patapsco Valley
3 stops
2 Days · Young Families
Patapsco Valley (Ellicott City, Sykesville), Maryland
Cobblestones & Cascades: A Family Weekend in the Patapsco Valley
4 stops
2 Days · Couples
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Waterlight & Wild Marsh: A Two-Day Eastern Shore Escape
5 stops
2 Days · Young Families
Annapolis area, Maryland
Sailboats, Storybook Streets & Salt Air: 2 Days in Annapolis with Little Ones
4 stops
2 Days · Young Families
Baltimore area, Maryland
Splash Pools & Star-Spangled Skies: A Family Weekend in Baltimore
4 stops
3 Days · Active Retirees
Baltimore area, Maryland
Harbor Light & Hallowed Ground: Three Autumn Days in Baltimore
10 stops
2 Days · Couples
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Light & River Song: A Fall Escape to the Patapsco Valley
4 stops
2 Days · Couples
Baltimore area, Maryland
Harbor Light & Fort Walls: A Baltimore Weekend for Two
7 stops
3 Days · Active Retirees
Patapsco Valley (Ellicott City, Sykesville), Maryland
Millstones & Foliage: Three Autumn Days in the Patapsco Valley
8 stops
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
2 Days · Couples
Annapolis area, Maryland
Brick, Bay, and Sailboat Light: Two Days in Annapolis
5 stops
2 Days · Young Families
Annapolis area, Maryland
Sailboats, Statehouses & Sandy Toes: A Family Weekend in Annapolis
4 stops
3 Days · Active Retirees
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Water Light & Wooden Boats: Three Days on the Eastern Shore
6 stops
2 Days · Young Families
Baltimore area, Maryland
Splash, Sail, and Stroll: A Gentle Baltimore Harbor Weekend for Little Ones
3 stops
2 Days · Couples
Baltimore area, Maryland
Harbor Light & Cobblestone Nights: Two Days in Baltimore
7 stops
2 Days · Couples
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Harbor Nights: A Two-Day Eastern Shore Escape
6 stops
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
3 Days · Active Retirees
Baltimore area, Maryland
Harbor Light & Hallowed Ground: 3 Days in Baltimore
8 stops
2 Days · Couples
Annapolis area, Maryland
Brick, Sail & Marsh Light: Two Days in Annapolis
5 stops
3 Days · Active Retirees
Annapolis area, Maryland
Brick, Bay, and Marsh Light: Three Unhurried Days in Annapolis
6 stops
3 Days · Young Families
Baltimore area, Maryland
Harbor Light & Fort Walls: 3 Days in Baltimore with Little Ones
7 stops
3 Days · Young Families
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Wheels & Maple Leaves: A Family Weekend in the Patapsco Valley
6 stops
3 Days · Young Families
Annapolis area, Maryland
Sailboats, Cobblestones & Quiet Waters: 3 Days in Annapolis with Little Ones
4 stops
3 Days · Couples
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light and Harbor Glow: 3 Days on Maryland's Eastern Shore
6 stops
3 Days · Couples
Baltimore area, Maryland
Harbor Light & Hilltop Views: A Baltimore Escape for Two
9 stops
3 Days · Young Families
Baltimore area, Maryland
Splash Pads & Salt Air: 3 Gentle Days in Baltimore with Little Ones
7 stops
3 Days · Young Families
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Harbor Days: 3 Days on Maryland's Eastern Shore with Little Ones
6 stops
3 Days · Couples
Annapolis area, Maryland
Brick, Sail & Marsh Light: A Chesapeake Weekend for Two
6 stops
3 Days · Solo
Ocean City area, Maryland
Salt Air & Wild Horses: Three Days Solo in Ocean City
6 stops
2 Days · Active Retirees
Ocean City area, Maryland
Salt Air & Slow Mornings: Two Days Along Ocean City's Shore
3 stops
3 Days · Teen Families
Ocean City area, Maryland
Boardwalk Lights & Wild Ponies: A Family Weekend on Maryland's Coast
6 stops
3 Days · Active Retirees
Ocean City area, Maryland
Salt Air & Slow Mornings: 3 Days in Ocean City
5 stops
2 Days · Couples
Ocean City area, Maryland
Salt Air & Wild Horses: A Couples' Escape to Ocean City
4 stops
2 Days · Young Families
Ocean City area, Maryland
Salt Air & Small Steps: A Family Weekend in Ocean City
3 stops
3 Days · Couples
Ocean City area, Maryland
Salt Air & Wild Horses: 3 Days in Ocean City
6 stops
Showing 60 of 83 — explore all of Maryland.
Maryland's weekend getaways span coastal charm, historic towns, and scenic valleys—each with itineraries tailored to different travel styles and seasons. This collection features 16 curated itineraries across five key destinations: Annapolis area, Patapsco Valley, Baltimore area, Eastern Shore, and Ocean City area. Whether traveling solo, with family, or seeking a spring escape or fall retreat, visitors will find options ranging from two to three days that highlight local history, natural beauty, and waterfront experiences.
Frequently Asked Questions
What types of itineraries are available?
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The collection includes 16 itineraries designed for various travel styles: family-focused escapes, solo adventures, and seasonal getaways. Itineraries range from 2 to 3 days and span destinations including Annapolis, Patapsco Valley, Baltimore, Eastern Shore, and Ocean City.
Which destinations are covered in this guide?
⌄
The guide features five main destinations: Annapolis area, Patapsco Valley (including Ellicott City and Sykesville), Baltimore area, Eastern Shore (including Chestertown, Easton, and St. Michaels), and Ocean City area.
Are there itineraries for families with children?
⌄
Yes. Family-focused itineraries are available, including 'Sailboats, Sandcastles & State House Steps' in Annapolis, 'Mill Wheels & River Giggles' in Patapsco Valley, and 'Marsh Light & Sandy Toes' on the Eastern Shore.
What about solo travel options?
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Solo travelers have several options, including 'Millstone & Mist: A Solo Fall Wander Through the Patapsco Valley,' 'Marsh Light & Harbor Quiet: Two Days Alone on Maryland's Eastern Shore,' and 'Harbor Light & Cobblestone Nights: 3 Days Solo in Baltimore.'
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Or browse every Maryland destination.