Twinkling lights, cozy inns, and waterfront charm. Celebrate the holidays with a long weekend in Talbot County.
All month long, Talbot County sparkles with parades, concerts, and festive shopping. Plan your visit for December 4-7, 2025 to catch some of the county’s signature traditions, or choose another weekend during the holiday season. Whenever you arrive, you’ll find plenty of holiday magic on Maryland’s Eastern Shore.
Day 1: Cocktails, Candlelight, and Holiday Charm
A Festive First Night
Check into the historic Tidewater Inn—your weekend retreat in the heart of Easton. After settling in, head downstairs for happy hour and sip a classic cocktail or savor a glass of wine. Next, stroll through downtown for Starlight Shopping, when shops stay open late and the streets glow with twinkling lights and holiday cheer. Cap the evening with a candlelit dinner at Scossa (don’t miss the risotto with butternut squash and bay scallops) before tucking into your room for the evening.
Day 2: Seafood, Sips, and Talbot County’s Creative Spirit
A Harmony of Eastern Shore Flavors
Venture to nearby St. Michaels, a picturesque harbor town known for its maritime heritage, for a leisurely lunch at Chesapeake Landing featuring Maryland’s “holy trinity of seafood”—crab cakes, oysters, and rockfish. Next, enjoy a tasting at St. Michaels Winery or Lyon Rum, then linger over local works at Studio B Art Gallery. In the evening, return to Easton for a performance at the historic Avalon Theatre. On Friday, December 5, don’t miss Gut, Wind, and Wire: Drive the Cold Winter Away—or choose from other holiday concerts and local favorites in the Avalon’s December lineup. The festive lights downtown will still be glowing as you step out, making for a charming stroll back to the Tidewater Inn.
Day 3: Unwind and Explore
A Picture-Perfect Day in Oxford
Bundle up for a short stroll to Weather Gage Coffee for expertly brewed coffee and a warm pastry. From there, indulge in a massage or facial* at Terrasse Spa–inside the Tidewater Inn. Next, take the short, scenic drive to Oxford, a charming waterfront village. In the evening, gather with locals for the Lighting of the Trees, a beloved tradition that transforms the dock—and the historic Oxford-Bellevue Ferry—into a holiday postcard. Finally, settle in with a waterside seafood dinner at Doc’s Sunset Grille, located in the nation’s oldest inn.
*Be sure to book in advance, as appointments fill quickly during the holiday season.
Day 4: Brunch & Byways
A Fond Farewell
Ease into your final morning with brunch at The Wardroom, a chic market-bistro in Easton offering creative breakfast plates in a cozy setting. Depart with the glow of a holiday weekend well spent—already dreaming of your return to Talbot County.