Roots & Tides

Explore the timeless traditions and deep maritime roots of Western Shore towns along the Chesapeake Bay. Go sailing, bird watching, museum hopping or just relax on a sandy beach.

The recreational opportunities are plentiful with each golden Chesapeake Bay day. Enjoy a relaxing beach getaway, navigate the bay’s waters, visit a heritage site or savor a delicious seafood meal. From bayside towns to fishing communities, this byway showcases the history and culture of this region.

Annapolis to Fairhaven

Including MD 2, MD 253, MD 468, MD 256 & MD 423

Begin in Annapolis, where there are more 18th-century buildings than any other city in America. Visit the Maryland State House, which served as the nation’s capital in 1783, and the Banneker-Douglass-Tubman Museum to learn about the area’s African-American heritage. Also available are guided walking tours of the U.S. Naval Academy, featuring glimpses of a midshipman’s life and a history that dates back to Revolutionary War hero John Paul Jones.

Of course, no trip to “America’s Sailing Capital” is complete without a fishing excursion or relaxing charter boat ride. Take a sailing cruise on the Schooner Woodwind where Chesapeake Storyteller Capt. Jennifer Kaye will point out wildlife seen along the way. Or try a cruise from Watermark Journey to discover the Chesapeake's heritage. Finish up with a delicious seafood dinner or unwind at a local pub.

Head south into Edgewater and tour Historic London Town and Gardens, where archaeological digs have unearthed artifacts dating back to the 18th century. Gardens and reconstructed colonial buildings are also located on the 23-acre property.

Many sites along this byway are part of the Chesapeake Bay Gateways Network, which connects visitors to history, culture and recreation along the bay and its tributaries. One official gateway is the Smithsonian Environmental Research Center, which encompasses 2,800 acres of forest, cropland, pasture, freshwater wetlands, tidal marshes and estuaries. Family-oriented activities include hiking, kayaking and guided canoe tours.

Check for powerboat and sailboat rentals in Edgewater, or continue south and charter a ketch in the 360-year-old Quaker settlement of Galesville. Nearby is another Chesapeake Bay Gateway, a restored waterman’s cottage in Shady Side known as the Captain Salem Avery Museum.

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