MileHacker Logo
Day Trips from Chesapeake Bay

Day Trips from Chesapeake Bay

Chesapeake Bay Maryland, USA Travel Guide

Washington D.C.

Approximately 30-60 minutes drive from Annapolis or Baltimore, traffic variations.

Nation'the nation's capital, home to Smithsonian museums (many with free admission), iconic national monuments (Lincoln Memorial, Washington Monument), and federal government buildings (U.S. Capitol, White House). A full day (8-10 hours) covers a few attractions. Focus on 1-2 Smithsonian museums and a walk along the National Mall.

Transportation Options

  • The MARC commuter train connects Baltimore Penn Station to Washington D.C.'s Union Station. Amtrak also links these urban areas.
  • Long-distance bus services (Greyhound, Megabus) connect Baltimore to D.C.
  • Direct driving is possible, but traffic and car parking in D.C. Can be challenging.
  • Many companies arrange bus tours from Baltimore or Annapolis to D.C.

Nearby Destinations

Several major U.S. Cities and historic sites are within a comfortable day-trip distance from the Chesapeake Bay region, notably from Annapolis and Baltimore.

Gettysburg, Pennsylvania

Approximately 1.5-2 a drive of hours from Baltimore. Site of the pivotal Civil War battle in July 1863. Battlefield tours, a national military park, and a visitor center with a museum await. A full day (8-10 hours) provides a comprehensive battlefield tour (self-guided audio tour, bus tour, or licensed guide) and a visit to the visitor center museum.

Transportation

  • Mainly accessible by car.
  • No direct public transport from the Bay area.
  • Self-guided or guided tours available.

Ocean City, Maryland

Approximately 2.5-3 hours drive from Annapolis (across the Bay Bridge, via US-50). Popular Atlantic Ocean beach resort city with a long boardwalk, amusement parks, and varied nightlife. It features a different coastal experience in comparison with the Bay. A full day (8-12 hours) allows for beach time, boardwalk exploration, and amusements. Factor in significant travel time, especially for Bay Bridge traffic on summer weekends.

Transportation

  • Mainly accessible by car.
  • Prepare for potentially long traffic delays on summer weekends.
  • Beach-focused activities.

Philadelphia, Pennsylvania

Getting There

  • Amtrak offers direct train service from Baltimore Penn Station.
  • Long-distance bus options are available.
  • Direct driving is an option.
  • Approximately 2 hours drive from Baltimore.

Organized Tour vs. Independent Travel

  • Organized tours for D.C. Or Gettysburg suit guided experiences.
  • Tours handle logistics and transportation.
  • Independent travel has flexibility.
  • A rental car aids exploring the wider Bay region and places with limited public transport.

Travel Comparison

  • Organized ToursGuided, structured
  • Independent TravelFlexible, self-paced
  • D.C. & GettysburgWell-suited for tours
  • Chesapeake BayBest explored independently
  • Rental CarFreedom to roam
  • Public TransitUrban areas only
  • LogisticsTours handle it
  • Hidden GemsIndependent discoveries

Travel Tip

When planning day trips, consider travel duration and local traffic patterns, especially for destinations across the Bay Bridge during peak season.

Natural Escapes

Beyond the immediate Bay, the region has opportunities for natural excursions, highlighting diverse ecosystems and landscapes.

Assateague Island National Seashore

Wild horses and unspoiled natural beaches. Excellent for wildlife viewing, beachcombing, and camping. Located on the Atlantic side of Maryland, approximately 2.5-3 hours drive from Annapolis/Baltimore.

Patuxent River Park

Offers diverse habitats, walking trails, and canoe/kayak rentals on the Patuxent River. Close TO 45 minutes to 1 hour drive from Annapolis.

Jug Bay Wetlands Sanctuary

A research and education center with trails and boardstrolls through tidal freshwater wetlands, for birdwatching and environmental education. Approximately 45 minutes drive from Annapolis.

Blackwater National Wildlife Refuge

An expansive area of marshlands, forests, and open water. It stands out as a prime birdwatching location and features a scenic driving loop.

Activities

  • Prime birdwatching opportunities.
  • A scenic driving loop to explore.
  • Vast marshlands and forests.

Chesapeake Bay Scenic Byway

This designated route winds through charming towns and pastoral landscapes on each of the Eastern and Western Shores. It has picturesque views of the Bay and its surrounding countryside.

Features

  • Charming towns and countryside scenery.
  • Views of Eastern and Western Shores.
  • Picturesque Bay scenery.

Seasonal Natural Phenomena

Migratory BirdsPeak birdwatching in spring and fall.
WaterfowlWintertime means vast numbers to the Bay.
Coastal ExplorationYear-round beachcombing.
Inland TrailsHiking enjoyable in spring and fall.
Refuge VisitsBlackwater is a prime spot.
Scenic DrivesEnjoy the Bay Byway any season.

Nature Explorer's Note

  • Explore Bay beaches for relaxed days: Sandy Point State Park, North Beach, or Chesapeake Beach.
  • Eastern Shore farmland or Southern Maryland tidewater region for peaceful escapes.
  • Maryland's Appalachian region (Cunningham Falls, Gambrill State Park) for hiking.
  • Peak birdwatching: spring and fall at refuges like Blackwater.
  • Winter: vast numbers of migratory waterfowl on the Bay.

Cultural Excursions

Extend your cultural exploration beyond the immediate Bay cities to discover more layers of Maryland's and America's past.

Historic St. Mary's City

Maryland's first capital, founded in 1634. Now a living history museum, it features reconstructed buildings, active archaeological digs, and a replica of the Maryland Dove ship. Approximately 1.5-2 hours drive south of Annapolis.

Experience

  • Reconstructed historic buildings.
  • Active archaeological digs.
  • Replica of the Maryland Dove ship.

Sotterley Plantation

One of the oldest surviving Tidewater plantations in Maryland. It has insights into colonial life, the history of slavery, and agricultural techniques. Approximately 1.5 hours by car south of Annapolis.

Learn About

  • Colonial life.
  • History of slavery.
  • Agricultural practices.

Antietam National Battlefield

Site of the bloodiest single-day battle in The history of the united states during the Civil War. A sobering and informative visit, approximately 1.5-2 hours west of Baltimore.

Visit

  • Civil War battle site.
  • An informative and reflective experience.
  • Located west of Baltimore.

Rural Villages & Agricultural Areas

Explore small towns on the Eastern Shore like Oxford, Chestertown, or Rock Hall for a glimpse into traditional Bay life and waterman culture. Visit local ranches and wineries, notably during harvest season.

Discover

  • Traditional Bay life.
  • Waterman culture.
  • Agricultural side of the region.

Pilgrimage Sites

Basilica of the National Shrine of the Assumption of the Blessed Virgin Mary (Baltimore): America's First Cathedral, a significant historic Catholic landmark, worth visiting for its architecture and religious importance.

Architectural Beauty

The Basilica's neoclassical design is remarkable, making it an architectural gem in Baltimore.

Religious Significance

A site for religious reflection and historical insight into American Catholicism.

America's First

A landmark with deep roots in US history.

Cultural Explorer Tip

Many smaller towns and rural areas offer neighborhood museums and historical societies that provide a dive into particular local histories.

Multi-Day Extensions

For those with more time, combining a Chesapeake Bay trip with neighboring regions creates a more comprehensive Mid-Atlantic experience.

Recommendations for Adding 1-3 Days

1

Washington D.C. + Chesapeake Bay

Spend 2-3 days immersing yourself in D.C.'s museums, monuments, and political history. Transition to Annapolis and the Eastern Shore for Bay-centric experiences. This combination blends urban exploration and coastal charm.

2

Ocean City/Delaware Beaches + Eastern Shore

After exploring the Chesapeake Bay, dedicate 2-3 days to the Atlantic coast beaches of Maryland (Ocean City) or Delaware (Rehoboth Beach, Bethany Beach). This provides a different coastal environment with ocean waves, boardwalks, and beach town vibes.

3

Logical Next Destinations

Pennsylvania (Philadelphia, Lancaster, Gettysburg); Virginia (Richmond, Colonial Williamsburg/Jamestown, Virginia Beach); New York City (major metropolitan area).

Transportation Connections

  • The Mid-Atlantic region features superb road and rail links.
  • Amtrak train service to major cities: Philadelphia, New York, and Richmond.
  • Major interstates (I-95, US-50) offer direct driving routes to neighboring states.
  • Consider a rental car for flexibility in regional exploration.
  • Airports like BWI are well-connected for arrivals/departures.
  • Public transit options within major cities are common.

Suggested Routes for Longer Regional Travel

  • Historic Triangle Route: Begin in Baltimore or Annapolis (Chesapeake Bay). Head south to Washington D.C., then Richmond, and finally to Colonial Williamsburg/Jamestown/Yorka town in Virginia. A deep dive into early Us history.
  • Bay to Beach Route: Explore Chesapeake Bay (Annapolis, Eastern Shore towns, wildlife refuges). Drive east across the Bay Bridge to Ocean City, Maryland, or the Delaware beaches (e.g., Rehoboth Beach, Bethany Beach) for a classic Atlantic Ocean beach vacation.
  • GetYourGuide: Find more day trip ideas and book experiences.

Extended Travel Considerations

Explore more of the Mid-Atlantic. Combine your Bay visit with nearby metropolises for a rich historical and cultural experience. Travel logistics are straightforward with good highway and rail connections.
Day Trips from Chesapeake Bay. Excursions, Nearby Cities, Tours