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19 Sep 2024
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Chesapeake Bay Road Trip Itinerary

Chesapeake Bay Road Trip Itinerary Overview

Embark on a captivating journey around the Chesapeake Bay with this well-curated road trip itinerary. Your adventure begins in Annapolis, MD, known for its historic charm, waterfront ambiance, and the prestigious United States Naval Academy. Dive into the rich maritime heritage at the Chesapeake Bay Maritime Museum in St. Michaels, where you'll explore exhibits and historic boats offering insights into the area's nautical past.

Next, nature enthusiasts will marvel at the Blackwater National Wildlife Refuge, a sanctuary brimming with diverse ecosystems and wildlife-watching opportunities. Continue your journey to Calvert Cliffs State Park, where the dramatic, fossil-studded cliffs along the bay, coupled with serene hiking trails, beckon fossil hunters and nature lovers alike.

Conclude your road trip at Point Lookout State Park, situated at the southernmost tip of Maryland. This historical site offers stunning bay views, a peek into Civil War history, and a variety of outdoor activities, including camping, fishing, and wildlife observation. Each stop on this itinerary promises a unique experience that beautifully captures the essence of the Chesapeake Bay region.


Recommended Activities

  • Trip Point Pin1

    Annapolis, MD

    Annapolis is known for its historic charm, vibrant waterfront, and as the sailing capital of the United States. The city offers delicious seafood, picturesque streets, and the United States Naval Academy.
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  • Trip Point Pin2

    Chesapeake Bay Maritime Museum, St. Michaels

    The Chesapeake Bay Maritime Museum in St. Michaels provides a fascinating glimpse into the rich maritime heritage of the Chesapeake Bay area, featuring exhibits, historic boats, and insightful tours.
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  • Trip Point Pin3

    Blackwater National Wildlife Refuge

    Blackwater National Wildlife Refuge is a haven for wildlife enthusiasts, offering opportunities for bird watching, hiking, and observing the diverse ecosystems of wetlands, forests, and open fields.
    Open Google Maps Button
  • Trip Point Pin4

    Calvert Cliffs State Park

    Calvert Cliffs State Park is renowned for its stunning fossil-laden cliffs along the Chesapeake Bay, scenic hiking trails, and a serene beach that offers excellent opportunities for fossil hunting and picnicking.
    Open Google Maps Button
  • Trip Point Pin5

    Point Lookout State Park

    Point Lookout State Park is a historic and scenic spot located at the southern tip of Maryland. It's known for its beautiful bay views, rich Civil War history, camping, fishing, and abundant wildlife.
    Open Google Maps Button

Restaurants

  • Restaurant Icon

    The Federal House Bar & Grille

    4.3
    $$$$

    The Federal House Bar & Grille

    Located in a historic building in Annapolis, this restaurant offers a unique blend of American cuisine with a historic ambiance.
    4.3
    $$$$
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    The Crab Claw Restaurant

    3.9
    $$$$

    The Crab Claw Restaurant

    Situated in St. Michaels, this iconic seafood restaurant offers fresh crabs and stunning waterfront views.
    3.9
    $$$$
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    Suicide Bridge Restaurant

    4.4
    $$$$

    Suicide Bridge Restaurant

    Located near Blackwater National Wildlife Refuge, known for its picturesque views and delicious seafood, especially their famous crab cakes.
    4.4
    $$$$
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    The Ruddy Duck Brewery & Grill

    4.4
    $$$$

    The Ruddy Duck Brewery & Grill

    This brewery and grill in Solomon's Island offers craft beers and a cozy atmosphere, making it a great stop near Calvert Cliffs State Park.
    4.4
    $$$$
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    Courtney's Restaurant & Seafood

    4.3
    $$$$

    Courtney's Restaurant & Seafood

    A hidden gem near Point Lookout State Park, this family-run restaurant serves fresh, locally caught seafood in a quaint and charming setting.
    4.3
    $$$$
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Hotels

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    Historic Inns of Annapolis

    4.6

    Historic Inns of Annapolis

    These charming inns offer a unique stay in the heart of Annapolis, combining modern comforts with historic elegance and character.
    4.6
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    The Inn at Perry Cabin

    4.5

    The Inn at Perry Cabin

    Located in St. Michaels, this luxurious waterfront hotel offers a serene escape with stunning views, a spa, and fine dining.
    4.5
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    Black Walnut Point Inn

    4.7

    Black Walnut Point Inn

    Situated on a secluded point at Tilghman Island, this quaint inn offers panoramic views of the Chesapeake Bay, making it ideal for a peaceful retreat.
    4.7
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    Solomon's Victorian Inn

    4.9

    Solomon's Victorian Inn

    A unique bed and breakfast located in a beautifully restored Victorian house in Solomon's Island, close to Calvert Cliffs State Park.
    4.9
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    Island Inn & Suites, Ascend Hotel Collection

    4

    Island Inn & Suites, Ascend Hotel Collection

    Located near Point Lookout State Park, this hotel offers rooms with private balconies overlooking St. George Island and exceptional sunset views.
    4
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Local Events & Happenings

  • Event Icon

    Sam Hunt w/ Austin Williams

    Sam Hunt w/ Austin Williams

    The event will take place at Calvert Marine Museum in Solomons.
    Map IconCalvert Marine Museum in Solomons (15.63 mi)
    Calendar Icon16 Aug 2025
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    Natalie Merchant

    Natalie Merchant

    The event will take place at Avalon Theatre - MD in Easton.
    Map IconAvalon Theatre - MD in Easton (22.27 mi)
    Calendar Icon22 Nov 2025
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    David Sedaris

    David Sedaris

    The event will take place at Avalon Theatre - MD in Easton.
    Map IconAvalon Theatre - MD in Easton (22.27 mi)
    Calendar Icon14 Feb 2026
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    The Wood Brothers w/ Mason Via

    The Wood Brothers w/ Mason Via

    The event will take place at Maryland Hall for the Creative Arts in Annapolis.
    Map IconMaryland Hall for the Creative Arts in Annapolis (34.16 mi)
    Calendar Icon12 Aug 2025
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    Donavon Frankenreiter

    Donavon Frankenreiter

    The event will take place at Rams Head On Stage in Annapolis.
    Map IconRams Head On Stage in Annapolis (34.16 mi)
    Calendar Icon13 Aug 2025
    Picture for Donavon Frankenreiter
  • Event Icon

    Sara Evans

    Sara Evans

    The event will take place at Rams Head On Stage in Annapolis.
    Map IconRams Head On Stage in Annapolis (34.16 mi)
    Calendar Icon15 Aug 2025
    Picture for Sara Evans
  • Event Icon

    The Doo Wop Project (21 & Over)

    The Doo Wop Project (21 & Over)

    The event will take place at Rams Head On Stage in Annapolis.
    Map IconRams Head On Stage in Annapolis (34.16 mi)
    Calendar Icon16 Aug 2025
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Travel Gems from Reddit

  • Reddit Icon

    Hey guys, looking for suggestions for a fun road trip route. All young men, Open to route detours. ... The route you planned is a 1 day trip down, and 1 day trip back. So plea...

    Road-trip suggestions!!

    Hey guys, looking for suggestions for a fun road trip route. All young men, Open to route detours. ... The route you planned is a 1 day trip down, and 1 day trip back. So plea...

    /r/maryland
  • Reddit Icon

    Chinatown is fun and has lots of tasty restaurants, Adam's Morgan and DuPont Circle have awesome places to eat, drink, be merry, and hang out, visiting the Mall, etc. The shor...

    Any recommendations for places to visit in the Chesapeake Bay area ...

    Chinatown is fun and has lots of tasty restaurants, Adam's Morgan and DuPont Circle have awesome places to eat, drink, be merry, and hang out, visiting the Mall, etc. The shor...

    /r/travel
  • Reddit Icon

    Other's have pointed out Calvert Cliffs is a good place, but it is a good long hike to the beach if you've got small kids. When my kids were in elementary school we had an ann...

    looking for a good location in chesapeake bay for shark teeth ...

    Other's have pointed out Calvert Cliffs is a good place, but it is a good long hike to the beach if you've got small kids. When my kids were in elementary school we had an ann...

    /r/maryland
  • Reddit Icon

    Looking for recommendations for anniversary trip My husband and I are celebrating our 20 year anniversary in September and are looking to do a weekend away on the Chesapeake. ...

    Looking for recommendations for anniversary trip

    Looking for recommendations for anniversary trip My husband and I are celebrating our 20 year anniversary in September and are looking to do a weekend away on the Chesapeake. ...

    /r/maryland

Music for Your Journey

  • Music Icon

    John Denver - Take Me Home, Country Roads

    John Denver - Take Me Home, Country Roads

    A classic road trip anthem that perfectly captures the spirit of traveling through beautiful landscapes.
    Listen on Spotify
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    Tom Petty - Runnin' Down A Dream

    Tom Petty - Runnin' Down A Dream

    An energetic track that complements the excitement of hitting the open road.
    Listen on Spotify
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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    A lively, upbeat song that celebrates the joy and unpredictability of a long drive.
    Listen on Spotify
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    Willie Nelson - On The Road Again - Live

    Willie Nelson - On The Road Again - Live

    An iconic traveling song that emphasizes the thrill of being on the move.
    Listen on Spotify
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    Don McLean - American Pie

    Don McLean - American Pie

    A nostalgic tune that provides a sing-along experience, perfect for long stretches of road.
    Listen on Spotify
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    Bruce Springsteen - Born to Run

    Bruce Springsteen - Born to Run

    A powerful rock anthem about freedom and the open road.
    Listen on Spotify
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    The Beatles - Here Comes The Sun - Remastered 2009

    The Beatles - Here Comes The Sun - Remastered 2009

    A feel-good track that brightens up any road trip, reminding you of the beauty around you.
    Listen on Spotify
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    Eagles - Hotel California - 2013 Remaster

    Eagles - Hotel California - 2013 Remaster

    A classic song that captures the allure and mystery of travels and new destinations.
    Listen on Spotify
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  • Music Icon

    Chuck Berry - Route 66

    Chuck Berry - Route 66

    A staple road trip song that celebrates the quintessential American highway and the adventure it brings.
    Listen on Spotify
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  • Music Icon

    Tracy Chapman - Fast Car

    Tracy Chapman - Fast Car

    A reflective track that suits the introspective moments of a road trip.
    Listen on Spotify
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