Annapolis, Maryland’s Eastern Shore & the Chesapeake Bay: An Extended Fall Weekend Trip

Day 1: Arrive in Baltimore & explore Easton and St. Michaels, Maryland

Given the short duration of our trip and the number of places we wanted to see and things we wanted to do, trip pre-planning and destination mapping were essential. We focused on historic and scenic locations that were noted as “must-see” visits by a number of travel blogs and Google searches and that were within an hour or so drive from Annapolis.

St. Michaels Marina

• After landing at BWI and picking up our rental car, my wife and I took a short 30-minute drive to Arnold, Maryland, where we stopped for lunch at The Point Crab House and Grill. Pre-planning for our trip identified this restaurant as a must stop for the seafood and for the location (Atlantic Marina along Mill Creek with access to the Chesapeake Bay). The crab soup, crab gazpacho, and crab cakes were amazing.

Crab soup at Point Crab House

• After lunch, we drove across the four-plus-mile Bay Bridge into Maryland's Eastern Shore, stopping first in the town of Easton. The Easton Historic district in the heart of town has almost 900 historic buildings dating from the 18th century. Specific things to see in Easton include:

  • Avalon Theater

  • Academy Art Museum

• From Easton, we drove 15 minutes to St. Michaels, Maryland, where we spent a couple of hours wandering around the boutique shops on historical Talbot Street. Specific things to see in St. Michaels include:

  • Chesapeake Bay Maritime Museum

  • Historic downtown (Talbot Street)

  • Scenic cruises and fishing charters

  • Architecture—historic colonial, federal, and Victorian homes

St. Michaels historic downtown

• From St. Michaels, we drove a little over an hour back across the Bay Bridge to Annapolis, Maryland, stopping for dinner at the Severn Inn, located on the Severn River with direct views across the river at the Naval Academy

Day 2: Explore Annapolis, Maryland

Our second day was focused exclusively on exploring Annapolis by foot and enjoying seafood. My wife and I were joined for the day by our son who lives in DC. Annapolis is ranked as one of the most walkable cities in the US. The town has not changed much since its inception in the 1600s, with centuries-old buildings that are now shops, boutiques, pubs, and restaurants.

Annapolis historic downtown

• We started our walking tour of Annapolis on Maryland Avenue, one of the oldest commercial streets in the US. Adjacent to Maryland Ave is the Maryland State House. Maryland Ave contains a number of historic buildings (Hammond-Harwood House and the Chase Lloyd house), along with antique and boutique shops.

• We followed Maryland Ave to Prince George Street, then to the city waterfront dock and the Market Space, where we had lunch at McGarveys Saloon and Oyster House (celebrating its 50th year). We enjoyed $1 oysters, clams, crab soup, and crab cakes along with Aviator Lager.

• After lunch, we walked up and down Main Street with its multitude of shops and restaurants before heading over to the neighborhood of Eastport—which is across the Spa Creek Bridge and offers great views of the waterfront, the Naval Academy, and the downtown area of Annapolis.

• We concluded our day in Annapolis by having dinner at Cantler's Riverside Inn. Cantler’s is a local institution in Annapolis and a “traditional” crab house—fresh seafood arrives by boat to the restaurant’s docks. We enjoyed a dozen large hard-shelled crabs (brown paper on the tables and mallets to pound out the fresh crab meat) along with crab soup, hushpuppies, and beer.

Cantler's Riverside Inn

• Additional things to see in Annapolis:

  • William Paca House and Garden (Georgian mansion and 18th-century gardens)

  • Banneker-Douglass Museum (African American history, art, and culture)

Day 3: Explore Annapolis and Chestertown, Maryland & return to Atlanta

The final day of our weekend trip was met with rain and wind from the nor'easter. We walked around Annapolis in the morning, then drove across the Bay Bridge to the town of Chestertown. Chestertown, founded in 1706, has been named one of the most beautiful and historic towns in the Mid-Atlantic. In addition to its well-preserved historic architecture, the town has a thriving arts and cultural scene and enjoys a location on the Chester River with access to the Chesapeake Bay. The town is also home to Washington College, founded with support from George Washington in 1782. Before heading back to the airport and catching our flight to Atlanta, we stopped for lunch at the Modern Stone Age Kitchen, a scratch-made sourdough bakery and restaurant.

Chestertown Marina

Getting to Annapolis

• BWI is the closest major airport to Annapolis (35 minutes)

• Washington DC's Ronald Reagan Airport is another option (70 minutes)

Getting to the Eastern Shore

• Distances from Annapolis:

  • Easton (1 hour)

  • St. Michaels (1 hour, 15 minutes)

  • Chestertown (1 hour, 10 minutes)

• Distances from Wilmington, Delaware:

  • Easton (1 hour, 37 minutes)

  • St. Michaels (1 hour, 45 minutes)

  • Chestertown (1 hour, 7 minutes)

About the Naval Academy

• Established in 1845, it sits on 338 acres in the historic section of Annapolis.

• All midshipmen live in Bancroft Hall, the largest college dormitory in the United States.

• The Naval Academy is open to the public (two forms of valid ID are required). Once inside the grounds, you can visit the world-class USNA Museum and just wander around the large campus

About the Chesapeake Bay Bridge

• 4.3 miles in length

• The first cars used the bridge in both directions in 1952

• Tolls

  • $2.50 for car with E-ZPass and $6 for video tolling

  • Toll only collected in eastbound direction

  • All electronic tolling—no toll booths

Seafood caught in the Chesapeake Bay

• Blue crabs, oysters, soft shell clams, bay scallops, rockfish, flounder, perch, croaker, black drum, bluefish, speckled trout, and cobia

Additional towns worth visiting in the Chesapeake Bay area

• Oxford, Maryland: Picturesque harbor and historic architecture; access to town is via ferry from Bellevue

• Cambridge, Maryland: Known for its waterfront and historic downtown

• Havre de Grace, Maryland: Located where the Susquehanna River meets the Chesapeake Bay

• Irvington, Virginia: Quaint and tranquil bayside village

• Yorktown, Virginia: Historic getaway

• Cape Charles, Virginia: Beaches

• Chincoteague, Virginia: Wild ponies

• Assateague Island: Wild ponies and lighthouses

For more inspiration and insider recommendations, visit our Maryland page.