2025 Fall Guide to Maryland’s Eastern Shore

Fall on Maryland’s Eastern Shore is nothing short of magical. Crisp air, colorful foliage, fresh seafood, and a calendar packed with local traditions make this season one of the best times to visit. Whether you’re a local looking for weekend plans or a traveler seeking the perfect autumn getaway, our 2025 Fall Guide has you covered.

Can’t-Miss Fall Festivals & Events

• Concours d’Elegance – Kent Island Yacht Club, Sept. 26–28
  Admire some of the world’s finest automobiles and classic boats against the scenic Chesapeake backdrop.

• Taste of Cambridge – Downtown Cambridge, Sept. 27
  Celebrate Eastern Shore cuisine with a cook-off, live music, local vendors, and family fun.

• Easton Fall Kick Off – Downtown Easton, Oct. 3–4
  Enjoy pumpkin carving, live music, and carriage rides in a charming fall atmosphere.

• Rockin’ the Porch – Centreville, Oct. 5
  A free, family-friendly music festival featuring seven stages, food vendors, and community vibes.

• Rock Hall Fall Fest – Rock Hall, Oct. 11
  Celebrate waterman heritage with live music, oysters, kids’ activities, and local crafts.

• Halloween Happening – Salisbury Zoo, Oct. 18 & 25
  A spooky family favorite with candy trails, costume contests, and games.

• Berlin Oktoberfest – Berlin, Oct. 18
  Authentic Oktoberfest fun with German food, music, and family-friendly activities.

• SunFest – Ocean City, Oct. 23–26
  One of the Shore’s biggest festivals with arts, crafts, live music, and food.

• OysterFest – St. Michaels, Oct. 25
  A seafood lover’s dream featuring oyster stew competitions, retriever shows, and plenty of local flavors.

• MactoberFest – Denton, Oct. 25
  Sample mac ’n’ cheese creations from top local chefs.

• Waterfowl Festival – Easton, Nov. 14–16
  Celebrate the Shore’s heritage with wildlife art, retriever demos, seafood, and family activities.

• Sea Glass Festival – St. Michaels, Nov. 22
  Shop artisan-made coastal jewelry, art, and décor at the Chesapeake Bay Maritime Museum.

Fall Markets & Free Activities

Eastern Shore farmers markets are bursting with seasonal produce, pumpkins, and autumn charm. Be sure to stop by:

• Emily’s Produce (Cambridge)

• Councell Farms (Cordova)

• Clayton’s Farms (Denton)

• Lockbriar Farms (Chestertown)

• Mill Creek Farms (Wye Mills)

• Family Affair Farm (Easton)

• JZ Farms (Federalsburg)

• Wright’s Market (Mardela Springs)

Free community traditions include:

• Outdoor Movie Night in Easton (Oct. 3) – Screening Monster House under the stars.

• First Fridays in Easton – Monthly art strolls with gallery openings and happy hour deals.

• Second Saturdays in Cambridge – Evening art walks and special shopping hours.

• Third Thursdays in Denton – Live music, local food, and games downtown.

Where to Eat, Sip & Savor

🍴 Cozy Dining Favorites

• Legal Assets – Easton

• Bombay Social – Cambridge

• Caroline’s Table – Denton

• Bridges Restaurant – Grasonville

• Luisa’s Cucina Italiana – Chestertown

🍇 Wineries & Vineyards

• Layton’s Chance (Vienna)

• St. Michaels Winery (St. Michaels)

• Crow Vineyard & Winery (Kennedyville)

• Cascia Vineyards (Stevensville)

☕ Coffee Shops to Warm Up

• Rise Up Coffee Roasters

• Black Water Bakery

• A Little Lovely Coffee House

• Java Rock Coffee House & Café

🦪 Local Oyster Spots
Find fresh, locally harvested oysters across Dorchester, Caroline, Talbot, Queen Anne’s, and Kent counties:

• KOOL Ice Seafood

• Blough’s Seafood

• Gay’s Seafood

• Chesapeake Landing

• Ford’s Seafood

• Choptank River Crab & Oyster Co.

• Lindy’s Seafood

• Cole’s Seafood House

• Hunter’s Seafood Market

• Chester River Seafood

Parks & Outdoor Escapes

For crisp autumn walks, picnics, or leaf-peeping, explore some of the Shore’s most scenic parks:

• Sailwinds Park (Cambridge)

• Idlewild Park (Easton)

• Chambers Park (Federalsburg)

• Wilmer Park (Chestertown)

• Millstream Park (Centreville)

• Pemberton Park (Salisbury)

Plan Your 2025 Fall Adventure

From oyster shucking contests and Oktoberfest brats to art strolls and sea glass treasures, Maryland’s Eastern Shore offers something for everyone this fall. Mark your calendars, bring your friends and family, and experience autumn the Shore way—colorful, flavorful, and unforgettable.

Cover Photo Credit: Jody Arneson