Surely Exciting Eastern Shore Itinerary
3 days of discovery and delight in the heart of Maryland’s Eastern Shore.
Talbot County is all about water, history and fun. Experience all three with this itinerary, featuring lots of landmarks, entertainment, water-based activities, and delicious food and drink destinations.
With an exciting food scene, adorable main streets and waterfront landmarks, Easton is the quintessential Eastern Shore town.
Get started at Out of the Fire, a lunch standby that specializes in wood-fired cuisine. Then walk down the street to check out the Academy Art Museum, a local gem with rotating art collections, workshops and educational sessions.
After a horse-drawn carriage ride through town with Tanglao Carriage Driving, head to the James Beard Award-winning Bas Rouge for refined European fare.
Top off the night by catching a show at the esteemed Avalon Theatre, a tastefully restored venue showcasing a wide variety of films and live performances. After the show, walk across the street and stay the night at the elegant and historic Tidewater Inn.
Known for its rich maritime history and refined feel, St. Michaels is a must-see waterfront town.
Rise Up, a popular café with artisanal coffees and comfortable digs, is a great place to start. Next, immerse yourself in the history and ecological significance of the Chesapeake Bay at the interactive Chesapeake Bay Maritime Museum.
Then heed the water’s call, and enjoy a unique perspective of the town with a sailing tour courtesy of St. Michael's Sailing Charters. Once you’re back on land, wet your whistle at Windon Distilling. This award-winning cra[ distillery is renowned for its inspired Lyon Rum varieties and offers tastings and tours to help guests learn about the rum-making process.
Finish your St. Michaels visit in style with a stay at the modern, centrally located Wildset Hotel.
Oxford is a quaint, inviting town that’s perfect for leisurely strolls, scenic water views and authentic dining options.
Start your day with the Oxford Museum audio walking tour, an engaging experience that lets you discover key landmarks and stories at your own pace. Then take a break with a scoop of fresh, homemade ice cream at Scoish Highland Creamery.
Next, hop on a Tumblehome Cruises boat tour, and learn more about the area’s wildlife and history as you cruise down the Tred Avon River.
Satisfy your seafood craving at The Robert Morris Inn, a storied hotel and restaurant with a vibrant ambiance and top-notch crab cakes. For another lodging option, try the adults-only, beachfront Sandaway Suites and Beach.