Heron on Dock at sunset

Eastern Shore Tour Ideas

Heron on Dock at sunset
Traverse Along the Chesapeake Country All American Road (CCAAR)
Watermens Monument  in Grasonville

A destination unto itself, the CCAAR traverses the extraordinary landscapes and waterscapes of the Eastern Shore, offering an epic journey through the lifestyles and livelihoods of generations of watermen, shipbuilders and farmers who have shaped the unspoiled landscape.  The CCAAR was recently elevated in status to an All-American Road, a title held by a small selection of iconic byways, including the Pacific Coast Highway.

Tubman in a Day
Harriet Tubman Underground Railroad State Park and Visitor Center

Begin at the Sailwinds Visitors Center. See the “Take My Hand Mural,” at the Harriet Tubman Museum & Educational Center.  Stop at a historic one-room schoolhouse and visit the Harriet Tubman Underground Railroad Visitor Center.  Next, see the Brodess Farm and the Bucktown General Store before concluding at the Linchester Mill.

Ultimate Guide to Underground Railroad Sites on the Shore
Frederick Douglass statue by Talbot County Courthouse

Hidden in the landscape, Maryland’s Underground Railroad sites await your exploration.  See where freedom fighters altered the course of history with their bravery, courage and sacrifice.  Maryland’s Eastern Shore is home to over 25 Network to Freedom designated sites, through the National Park Service, including a Frederick Douglass walking tour of St. Michaels and driving tour of Talbot County.

Maryland Crab & Oyster Trail Tour
Broiled crab cake from Suicide Bridge Restaurant
Dorchester County Tourism

Follow the seafood from the Chesapeake Bay to the Atlantic, with stops along the Eastern Shore to enjoy authentic experiences, focused on celebrating and savoring Maryland’s delectable seafood.

Best of the Sassafras
Senior couple drinking wine

Get up close and personal with alpacas while you learn at the Painted Sky Alpaca Farm & Fiber Mill; enjoy a meal at Molly's Restaurant for some of the best food on the Eastern Shore; and experience a tour and tasting at Crow Vineyard & Winery, an award-winning tourism venue that is helping to shape a wine country of note for Maryland’s Eastern Shore. 

Chesapeake City for a Day
Chesapeake City

Explore the area with a guided tour of the Thoroughbred horse farms; stop off at the Chesapeake & Delaware Canal Museum; dine on a delicious meal at Chesapeake Inn, where you might see a large container ship passing through.  Board the pontoon boat for a narrated cruise of the C&D Canal.

Chester River Cruise & Lunch
Chester river packet with a blue heron at sunset
Kent County Economic & Tourism Development

Cruise the Chester River aboard the River Packet from Chestertown and enjoy lunch at Watershed Alley.

Kent Island Experience
Orange crush

Take a scenic cruise aboard the Island Queen II from Kent Narrows. After your cruise, visit Fisherman’s Crab Deck for a true Maryland Crab Feast! Make sure to order a fresh orange crush because you’re in Crabs n’ Crushes Country! Visit Terrapin Nature Park and enjoy the trails while taking in breathtaking views of the Chesapeake Bay Bridge.

More on the Shore
Pemberton Park

Start the day with an interpretive tour of Pemberton Hall, built in 1741 by one of Salisbury’s founders. Next, is the Museum of Eastern Shore Culture for a tour of the cultural heritage and traditional arts of Delmarva’s various communities. Do a guided tour and scavenger hunt at the Salisbury Zoo, home to more than 100 animals including wild cats, wallabies, reptiles and Andean bears.  Experience an authentic Eastern Shore crab feast at the Red Roost Restaurant, a converted chicken house.   For more “Bird” entertainment, enjoy a seasonal baseball game with the Delmarva Shorebirds.

Smith Island Cruise
Dan Harrison

Head for Crisfield, the “Crab Capital of the World.”  Begin by visiting the historical J. Millard Tawes Museum and taking a driving tour of this historic town.  All aboard the Chelsea Lane Tyler for a leisure one-hour cruise to Smith Island.  Upon arrival to this quaint island, you will enjoy a traditional waterman’s lunch at the Bayside Restaurant.  Afterward, stroll the narrow streets or rent a golf cart, visit the Smith Island Cultural Center, and purchase a Smith Island Cake (the official state dessert) and fresh local seafood to take home.

All Aboard for St. Michaels
Chesapeake Bay Maritime Museum

Take a docent-led tour through a tribute of Maryland’s maritime heritage at the Chesapeake Bay Maritime Museum.  You will want to visit the screw-pile Hooper Strait Lighthouse.  Delectable fresh seafood awaits at the Crab Claw Restaurant, followed by a narrated tour aboard the 65-foot climate-controlled, Patriot.  Be sure to allow time for exploring the many shops, boutiques and galleries in St. Michaels.

Ocean City and Beyond the Beach
Ocean City Hilton

Ocean City is a crown jewel in mid-Atlantic resort travel. Always family-friendly and fun, Ocean City boasts a wide, clean beach, beautiful sunrises and soothing sunsets. Our restaurant scene is farm to table as well as traditional boardwalk fare. The Museums of Worcester County will enrich a visitors knowledge of history and traditions of this coastal, rural area. Wild ponies of Assateague Island will capture your imagination. The main streets and shopping of Berlin as well as the pub and eatery scene will refresh and revive. Ocean City and its surrounding area offer the best of the coastal resort life as well as a taste of enriching experiences.

Ag Tour on the Shore
Smokey Cat Lavender Farm
Smokey Cat Lavender Farm

Explore the many forms of the Eastern Shore’s #1 industry – agriculture. Tour Harvest Ridge Winery before heading to Outstanding Dreams Alpaca Farm. Shop at The Shore Gourmet before a cooking class and catered lunch at the Chesapeake Culinary Center.  Complete your day with a visit to the seasonal Smokey Cat Lavender Farm.