Rails, Sails & Stories Along the Chesapeake

Activities

Maryland invites groups to journey through two centuries of transportation, culture, and coastal charm

Set along the shores of the Chesapeake Bay, Maryland invites travelers to experience a destination where culture and coastal adventure come together in unforgettable ways.

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Watermark Cruises

Rails, Sails & Tales

Traverse 200 years of railroading history on Maryland’s scenic railways. Ride the rails to travel back in time and explore Maryland’s fascinating history and breathtaking landscapes. Discover the story of railroading in Maryland in beautifully preserved train stations and museums, brimming with railroading treasures, including the:

  • B & O Railroad Museum in Baltimore (where visitors can step directly into history as they discover the story of American railroading)
  • Chesapeake Beach Railway Museum in Chesapeake Beach (this is an excellent example of rural railroad architecture)
  • National Capital Trolley Museum in Wheaton (Experience early 20th-century transit as you travel two miles aboard a Washington Street Car and American Trolley or a European Tram)
  • Point of Rocks Railroad Station in Point of Rocks (Built in 1875, this charming Victorian station is on the National Register of Historic Places)

Sails and Tales

Cruise Maryland’s waterways with a Chesapeake Bay Storyteller to immerse yourself in an authentic Maryland experience. Discover Maryland from the water, see historic lighthouses, marvel at sandy beaches and bountiful wildlife, and uncover hidden maritime gems along the way, including

  • Watermark Cruises
  • Schooner Woodwind
  • Patriot Cruise at Chesapeake Bay Maritime Museum
  • Chesapeake Water Tours
  • Choptank Riverboat Company
  • Baltimore Rent-a-Tour (water taxi experience)
  • Ocean City cruises

Here are a few examples of Maryland’s popular group tours.

Annapolitan II

Baltimore’s Rail & Sails

This “All Aboard” tour begins at the Baltimore & Ohio Railroad Museum, the birthplace of American railroading, where your group can see, touch, and hear the most important American railroad collection in the world. Travel to the Inner Harbor and board the Annapolitan II for a 45-minute narrated harbor cruise to see famous neighborhoods like Fells Point, Federal Hill, the downtown skyline, and historical landmarks like the USS Constellation and Fort McHenry.

All Aboard for Frederick County

Get aboard a trip back in time, on the Walkersville Southern Railroad. See the turn-of-the-century railroad station, tool house, and ride in vintage 1920s passenger cars on a rail excursion through Maryland farm country. Dine at the Carriage House Inn, listed on the National Register of Historic Places; see the Catoctin Iron Furnace; and stop off at the Gateway Market to end the day.

Two Trains in Two Days/Railways & Waterways

Your trip begins at the historic Western Maryland Railway Station in downtown Cumberland. Learn how the C&O Canal National Historical Park, Western Maryland Railway, and B&O Railroad influenced the Queen City. Then, climb aboard the Western Maryland Scenic Railroad for lunch as you ascend 1,300 feet to the “Mountain City” of Frostburg. On your second day of adventure, visit the C&O Canal at Old Town to visit an original lockhouse and learn how the lock system worked. Cross the North Branch of the Potomac River to continue on the Potomac Eagle Scenic Railroad.

Grand Adventure in Garrett County

Travel to Oakland to visit the Garrett County Museum of Transportation and the Oakland B&O Museum. Both museums showcase the unique history of transportation in Garrett County. See the Casselman River Bridge, a stone arch bridge built in 1813 on the National Road; the Spruce Artisan Village, with a collection of unique artisans making their crafts; lunch at Penn Alps with several buffet options; and end with a stop at Hilltop Fruit Market & Candyland, with more than 900 varieties of candy.

For more travel tips and ideas for groups, be sure to Download the June edition of Leisure Group Travel and Subscribe for FREE


Contact Maryland Office of Tourism


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