Exploring Chesapeake Bay: A Black Traveler’s Guide
A couple enjoying an exuberant day of sailing on the Chesapeake Bay; (c) Visit Maryland
For many Black travelers, a journey through the Chesapeake Bay begins at City Dock in Annapolis. Once a bustling Colonial port, this historic waterfront was home to shipyards, warehouses, and lively taverns. Free Black workers and skilled craftsmen played a vital role in the city’s maritime industry.
Today, City Dock is a beautifully preserved site where visitors can stroll along the marina, enjoy waterfront dining, and soak in the region’s rich cultural history.
Our Annapolis Black Travel Guide highlights the cultural gems of Maryland’s capital city. After snapping a selfie next to the Alex Haley Memorial, explore the area’s vibrant restaurant scene. Savor fresh oysters, crab cakes, and rockfish—all staples of Chesapeake Bay cuisine.
Thomas Dorsey of Soul Of America with his Sister-Cousins at Alex Haley Memorial
To deepen your connection with the bay, book a tour with a certified Chesapeake Bay Storyteller listed on https://www.visitmaryland.org. These guides bring the history, ecology, and culture of the region to life. For an unforgettable experience, set sail with Bay Hunter Charter Fishing (bayhunters.com)—one of the best ways to enjoy the bay with family and friends.
Nothing says Maryland like a classic Chesapeake Bay crab feast. From April to November, indulge in steamed blue crabs, generously seasoned with Old Bay, a splash of beer, and cooked to perfection. Pair them with a cold National Bohemian beer (aka “Natty Boh”) or a local craft brew. If a hearty glass of wine or inventive cocktail better suits you, that works too!
The best part? Watching the process unfold—your host plucking fresh crabs from a bushel, then steaming them in oversized pots with a blend of secret spices, beer, Old Bay, and vinegar. Whether you’re a seasoned pro or a first-time crab picker, cracking open these flavorful crustaceans is a social event that brings everyone together.
For an authentic experience, visit legendary crab houses like Cantler’s Riverside Inn (Annapolis) or Harris Crab House (Kent Island).
Enjoy a mouth-watering Maryland Crab Feast for timeless memories with family & friends; (c) Visit Maryland
Boating & Black History Along the Chesapeake
The Chesapeake Bay, stretching 125 miles through Maryland, is a paradise for boaters. Glide past lush shorelines, historic lighthouses, and breathtaking sunsets, while spotting bald eagles, ospreys, and dolphins along the way. The bay is also a top spot for fishing, crabbing, and sailing.
When you cross the bay into Eastern Maryland, Kent Island is a hidden gem for Black travelers. Kent Island is a gateway to heritage sites, charter fishing, and scenic boat tours. It holds a deep connection to Black history—once part of the Underground Railroad, where freedom seekers braved the waters to escape to free states.
Explore these important landmarks and contact the AA Heritage Council about its annual Fish Fry:
• Historic African American Schoolhouse
• African American Heritage Council at 23620 Newtown Road, Worton, MD, 410-810-1416
Consider an overnight stay at Great Oak Manor for a peaceful retreat near the Choptank River Lighthouse. Nestled along the tidal Choptank River, this quaint riverside community is a peaceful escape, offering travelers a glimpse into Maryland’s Indigenous history and Chesapeake Bay culture.
Choptank’s name is believed to be a crude Anglicization of an Algonquian word in the area once home to the Choptank tribe before European settlers arrived.
Long Wharf at the Choptank River Lighthouse; (c) Visit Maryland
The Choptank River is perfect for kayaking, fishing, and boating. It’s also a tremendous landscape for outdoor lovers and birdwatchers of ospreys, herons, and bald eagles darting over the water.
Frederick Douglass & Maryland’s Eastern Shore
Just south of Kent Island is Talbot County, the birthplace of Frederick Douglass. Take a detour to visit Tilghman Island, dotted with charming B&Bs, or dock at Safe Harbor Great Oak Landing before unwinding with a drink at Jellyfish Joel’s Beach Bar.
History buffs and active travelers won’t want to miss these captivating sites & activities:
• Historic St. Mary’s City
• Calvert Marine Museum & Drum Point Lighthouse
• Chesapeake Bay Maritime Museum (St. Michaels)
• Outdoor Adventures & Waterfront Escapes
• Terrapin Nature Park – Hike scenic trails, relax on a quiet beach, and admire the Chesapeake Bay Bridge views.
• Blackwater Adventures – Rent kayaks or paddleboards to explore the bay’s hidden coves.
• Overnight Bay Escapes – Stay on Tangier Island, Scotland Yards Beach Rentals, or Point Lookout Sanctuary for a serene getaway.
A dad and son kayaking at Blackwater National Wildlife Refuge; credit Visit Maryland
Make Maryland Yours
Exploring Chesapeake Bay and indulging in Maryland’s famous crabs are more than just activities — they’re experiences deeply woven into the state’s culture. Whether you’re soaking in Black history, savoring fresh seafood, or setting sail for adventure, Maryland welcomes you to make unforgettable memories on the Chesapeake Bay.
PHONE: 877-333-4455
WEBSITE: https://www.visitmaryland.org