History Revealed Itinerary

Begin your journey at Black Water Bakery + Eats where you can enjoy another Eastern Shore favorite in a cup of Rise Up Coffee. Join a Harriet Tubman Tour to visit significant sites along the Underground Railroad, where young and old will appreciate the life and sacrifice of a Maryland legend. Grab a waterfront lunch at Portside Seafood Restaurant, then enjoy a Pie of the Day from Ava’s Pizzeria & Wine Bar. Experience an afternoon of maritime history by cruising along the Choptank River with Skipjack Nathan of Dorchester. Visit Poplar Street for local seafood at community favorite, Jimmie & Sook’s, then grab a cone from Maiden Maryland Ice Cream. Head to the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina for amazing waterfront views.

Take a driving tour of a few of Salisbury’s historical landmarks, like the Pemberton Historical Park & Hall, Adkins Historical & Museum Complex, and the Charles H. Chipman Cultural Center. Refuel at Mogan’s Oyster House before embarking on an afternoon scavenger hunt of historical markers, a fun and engaging way to take in hundreds of years of history. Find Harriet Tubman’s Statue & Historic Marker, Historic Byrd Tavern, General Humphrey’s Cannon, and the Lynching in Wicomico County historical marker. After a full day, enjoy local cuisine at Brew River Restaurant, or Evolution Craft Brewing Co. Settle in for the night at Hampton Inn Salisbury or Courtyard by Marriott Salisbury.

For more small-town history, spend the day in the Historic District of Princess Anne, viewing pre-Revolutionary structures and Federal and Victorian Architecture buildings. Be sure to check out The William Geddes House, Somerset County Court House, The Washington Inn & Tavern, and Teackle Mansion. For lunch and dinner, stop by Beach to Bay Seafood, or soak up more history at The Washington Inn & Tavern. For dessert, head to Rebecca’s Ice Cream Parlor for frozen treats. For cozy accommodations, stay at The Washington Inn, The Richard Henson Center, or for literary Anglophiles, the Princess Anne Book Lovers Inn.

Begin your day in Pocomoke City, the “friendliest town on the Eastern Shore,” at Furnace Town Historic Site, nestled in the picturesque Pocomoke Forest. Tour the Living Heritage Village, and explore the sites and history of 19th-century buildings and artisan studios. Enjoy a waterfront lunch at Dockside Bar & Grill before diving back into local history at Delmarva Discovery Museum, Sturgis One Room School Museum, and the Costen House Museum. Then return to the waterfront for dinner at Don’s Seafood & Chicken House. Turn in for the night at Holiday Inn Express Pocomoke City, or for a more romantic setting, book a room at the River House Inn, a beautiful Victorian B&B on the river.

Wrap up your final leg of the journey with a ferry ride from Somers Cove Marina to Smith Island, Maryland’s only remaining inhabited offshore island group. Keep your ears tuned to the unique accent of the locals, largely unchanged since the first English settlers in the 1600s! Visit the Smith Island Cultural Center and grab a Smith Island Guide for more historical items and artifacts, and don’t forget to stop at Bayside Gifts next door for souvenirs. Bayside Inn Restaurant offers excellent streamed crabs fresh from the Chesapeake Bay. Save room for a slice of their famous Smith Island cake, Maryland’s State Dessert. Walk off lunch with a stroll through Ewell Village where you’ll find local shops and antique stores. Then spend your final evening at Smith Island Inn, or park your car in Crisfield and take the Captain Jason II ferry to the remote and peaceful Inn of Silent Music.