Explore Maryland’s Eastern Shore: Must-Do Fall Day Trips

Autumn is a magical time on Maryland’s Eastern Shore. Crisp air, colorful foliage, and seasonal charm make it the perfect season for exploring. Whether you’re seeking outdoor adventures, small-town charm, or family-friendly activities, the Shore offers countless memorable day trips just a short drive from home. Here’s a guide to help you plan the perfect fall outing.

Discover Local Orchards and Farms

Fall is synonymous with apple picking, pumpkin patches, and hayrides. Beyond the well-known spots, try Councell Farms in Easton or Lockbriar Farms in Chestertown for seasonal activities that bring the family together. From fresh cider and baked goods to farm markets brimming with local produce, a day spent at these farms captures the essence of autumn on the Shore.

Itinerary Idea – Easton & Chestertown Farm Day:

• 9:00 AM: Arrive at Councell Farms in Easton. Spend the morning exploring the pumpkin patch and field of fun (including corn mazes).

• 11:00 AM: Grab fresh cider and pastries before heading out.

• 12:00 PM: Drive around 30 minutes to Lockbriar Farms in Chestertown for ice cream, farm animals, and seasonal produce.

• 2:00 PM: Lunch at a local café like The Mainstay in Chestertown.

• 3:00 PM: Walk along Chestertown’s scenic waterfront or stop by the Riverside Gallery for local art.

Nearby Attractions:

• Chester River Lighthouse for photos and exploration

• Chestertown Historic District for charming streets and shops

Enjoy Scenic Trails and Wildlife

The Eastern Shore’s landscapes come alive in the fall. Try the Marsh Edge Trail in Cambridge or the Miles River Trails near Easton for hiking, biking, and wildlife spotting. Pack a picnic and enjoy the vibrant colors and peaceful surroundings of the season.

Itinerary Idea – Nature Escape:

• 8:30 AM: Start at Marsh Edge Trail. Hike through wetlands and forested paths, perfect for birdwatching.

• 11:00 AM: Brunch at a nearby café such as Black Water Bakery in Cambridge.

• 12:30 PM: Drive to the Miles River Trails for an afternoon walk or casual bike ride through scenic woodland and riverside paths.

• 3:30 PM: Stop at a local orchard or farm stand along the way for fresh apples.

• 5:00 PM: Wrap up with sunset views at Choptank River Marina or a nearby riverside park.

Nearby Attractions:

• Day boat rentals or kayaking on the Miles River

• Scenic drives along the Choptank River for fall foliage

Explore Charming Historic Towns

Eastern Shore towns offer history, culture, and seasonal charm. In the fall, Chestertown, Easton, and Oxford showcase colorful streets, boutique shopping, and local events. Each town has its own character, perfect for leisurely exploration.

Itinerary Idea – Historic Town Tour:

• 9:00 AM: Start in Chestertown with a walk along High Street and the historic downtown. Stop by local shops and the Farmers’ Market (if visiting on a weekend).

• 11:00 AM: Head to Easton to explore galleries, boutique shops, and the historic courthouse area.

• 12:30 PM: Lunch at a local favorite such as Legal Assets or Washington Street Pub.

• 2:00 PM: Drive to Oxford for an afternoon stroll along the waterfront, browsing local shops and cafes.

• 4:30 PM: Take a short ride on the Oxford-Bellevue Ferry to enjoy river views before heading home.

Nearby Attractions:

• Seasonal craft fairs and fall art shows

• Local wineries and breweries for tastings

• Scenic historic homes and gardens open for tours

Savor Waterfront Dining and Sunsets

Fall evenings are perfect for waterfront dining. Towns like Tilghman Island, Rock Hall, and Oxford offer cozy spots to enjoy seafood while taking in autumn sunsets over the Chesapeake Bay.

Itinerary Idea – Waterfront Evening:

• 3:30 PM: Arrive in Rock Hall or Tilghman Island for an afternoon stroll along the harbor.

• 4:30 PM: Explore local shops, galleries, or a nearby lighthouse.

• 5:30 PM: Enjoy dinner at a waterfront restaurant like The Tilghman Island Inn in Tilghman or Blue Heron Oyster House in Rock Hall.

• 6:30 PM: Watch the sunset over the water and take a peaceful evening walk before heading home.

Nearby Attractions:

• Kayak or paddleboard rentals for sunset paddling

• Local seafood markets to bring home a fresh catch

• Scenic drives along the bay for photography

Whether you’re picking pumpkins, hiking scenic trails, or enjoying a quiet afternoon in a historic town, Maryland’s Eastern Shore offers countless ways to embrace the beauty of fall. For those who fall in love with the region, Benson & Mangold Real Estate can help you find a home that allows you to enjoy these seasonal delights year-round.