Sign Up
Newsletter Signup
Free Fodor's Newsletter

Subscribe today for weekly travel inspiration, tips, and special offers.

Passport: Your weekly travel wrap-up
Today's Departure: Your daily dose of travel inspiration

Annapolis and Southern Maryland Travel Guide

  • Photo: Steven Frame / Shutterstock
  • Photo: Anton Albert / Shutterstock

Plan Your Annapolis and Southern Maryland Vacation

"Just at the mouth of the river, we observed the natives in arms. That night, fires blazed through the whole country and since they had never seen such a large ship, messengers were sent in all directions, who reported that a 'canoe' like an island had come with as many as there were trees in the woods."—Father Andrew White, recounting the arrival of

the Ark and the Dove in 1634.

Father White arrived in the New World in 1634 as a member of Lord Baltimore's contingent of 140 colonists. The two "canoes" the Native Americans spotted were the tiny sailing vessels that had just crossed the Atlantic to reach the southernmost tip of Maryland's Western Shore, where the Potomac River meets the Chesapeake Bay. The peninsula between the Potomac and the Patuxent rivers is today St. Mary's County—easily one of the state's most beautiful regions. It is gradually attracting development because of its easy access to Washington, D.C., to the north.

Like so much of Maryland south of Annapolis and Washington, many scenic drives throughout St. Mary's County bring together charming inland and waterside towns and historic sites. Hearty food and homey places to stay are easy to find.

Looking for an unusual find? Numerous liquor stores in St. Mary's County sell popular brands of U.S. beer in rare 8-ounce and 10-ounce cans.

The past is never far away from the present among the coves, rivers, and creeks of the Chesapeake Bay's lesser-known western shore. In the lively port of Annapolis, Colonial Maryland continues to assert itself. Today "Crabtown," as the state capital is sometimes called, has one of the highest concentrations of 18th-century buildings in the nation, including more than 50 that predate the Revolutionary War.

The region's counties—Anne Arundel, Calvert, Charles, and St. Mary's—have been supported since their 17th-century founding through tobacco fields and fishing fleets. More recently, the northern parts of the counties have emerged as prime residential satellites for the Annapolis–Baltimore–D.C. metro triangle; but despite the subdivisions and concomitant shopping centers, southern Maryland maintains much of its rural character. With the exception of the fair-weather getaway enclave Solomons Island and the archaeological site-in-progress Historic St. Mary's City, the region remains largely undiscovered. All the better for travelers who come to enjoy stunning water vistas, miles of scenic roads, dozens of historic sites, and a plethora of inns and bed-and-breakfasts on the water, in tiny towns, and in the fields and woodlands of its unspoiled countryside.

The long, narrow peninsula between the Patuxent River and the Chesapeake Bay is Calvert County, an area that has not yet been completely overrun by tourism. Two principal routes—Route 2 from Annapolis and Route 4 from Washington, D.C.—merge near Sunderland and continue on together to the county's southern tip. Exploring the bay-side and riverside communities to either side of the highway, as well as the inland sites and attractions, will immerse you quickly in the tangible history and heritage of agriculture and fishing. Although southern Maryland is best known as a fishermen and boaters' paradise, it is also popular with cyclists. Its flat terrain and relatively uncongested roads make for perfect conditions to tour the area by bike.

Read More
Updated 1/20/2014

Top Reasons To Go

  1. Experience Colonial History The U.S. Congress met in the Maryland State House from 1783 to 1784, and two significant events occurred during that time General George Washington resigned as commander-in-chief of the Continental Army and the Treaty of Paris was ratified.
  2. Salute the Navy at Annapolis The U.S. Naval Academy is the most important site in town. Don't miss its centerpiece, the bright copper-clad dome of the U.S. Naval Academy Chapel, beneath which lies the crypt of the Revolutionary War naval officer John Paul Jones.
  3. Return to the Golden Age of the Railroad At the Chesapeake Bay Railway Museum, housed in the railroad's 1898 track-side terminus, check out a glass-enclosed model of the town of Chesapeake Beach and a gleaming, black Ford Model T that once carried guests from the station to their hotels.
  4. Visit a 17th-Century British Settlement At Historic St. Mary's, the fourth permanent settlement in British North America and eventually the first (albeit short-lived) capital of Maryland, you can view ongoing restoration work in this much smaller, and less-refined, version of Williamsburg, Virginia.

When To Go

When to Go to Annapolis and Southern Maryland

Each season has its charms in southern Maryland. In the heat of summer the Chesapeake Bay provides boating and swimming. In fall, the changing col...

Read More

Travel Tips

Annapolis and Southern Maryland Travel Tips

See All

Advertisement

Advertisement

Trip Finder
Travel Deals