Fall Adventures Await: Scenic Day Trips from Maryland's Eastern Shore
- Willie
- Nov 12
- 3 min read
Fall is a beautiful time to wander the quiet corners of Maryland's Eastern Shore. With cooler air, softly glowing leaves, and a gentle festive spirit in the air, it's the perfect season to make memories. If you're staying at the historic Washington Hotel in Princess Anne--or planning to--there are some truly welcoming day-trip options that are open, inviting, and full of local charm.
1. Explore Chincoteague National Wildlife Refuge
Just a scenic drive from Princess Anne, Chincoteague National Wildlife Refuge offers a peaceful retreat surrounded by coastal marshes, dunes, and quiet waters. Fall is especially lovely here, when migrating birds arrive and the landscape feels open and serene.
Walk or bike along the Wildlife Loop Trail, take time to look for the famous Chincoteague ponies grazing along tall grasses, and visit the Assateague Lighthouse for a coastal view that captures the season's beauty. Whether you wander slowly or spend the entire afternoon exploring, this is a place that invites you to breathe deeply and take in the landscape.
2. A Day Trip to Ocean City's Boardwalk
Ocean City's shoreline is calm and refreshing in the fall months. The pace slows, the boardwalk relaxes, and the ocean takes on deeper, more dramatic hues. It's a beautiful time for a leisurely stroll, warm drink in hand, with the sound of waves nearby.
Browse open shops for local treats and seasonal flavors, enjoy small coastal cafes, or simply walk and watch the waves roll in. Without the summer bustle, the boardwalk feels spacious, inviting, and pleasantly unhurried.
3. Visit the Harriet Tubman Museum and Educational Center in Cambridge
A meaningful and reflective spot, the Harriet Tubman Museum and Educational Center honors the life and legacy of one of the Eastern Shore's most courageous figures. Tubman's story is tied deeply to this landscape--its waterways, fields, and hidden routes--and visiting in the fall, when the world quiets a bit, makes the experience even more resonant.
Inside the museum, exhibits, artwork, and personal stories help visitors connect to Tubman's remarkable journey and the role she played in the Underground Railroad. It is thoughtful, grounding, and worth the trip.
4. Go Antiquing Across Somerset County
If you love uncovering treasures from the past, Somerset County is full of antique shops and markets brimming with charm. From downtown Princess Anne to nearby Crisfield and Pocomoke, each stop offers a blend of history and character--vintage furniture, maritime finds, and art that reflects the region's coastal roots.
Whether you're searching for a keepsake or simply exploring, antiquing on the Eastern Shore is a relaxed way to spend a fall afternoon. The experience is less about the hunt and more about the joy of discovery--each piece holding a story that connects you to the heart of the Eastern Shore.
5. Celebrate Crisp Fall Mornings at Janes Island State Park
Only minutes from Princess Anne, Janes Island State Park is where winding waterways meet quiet forests and wide marsh views. This is a beautiful place to experience fall on the Eastern Shore at your own pace--by kayak, nature trail, or simply sitting and watching the tide move along the reeds.
Paddle through protected coves, walk along peaceful paths, or pause at the observation decks to watch herons drift overhead. Cool autumn air makes the park especially inviting for slow, unhurried exploration.
A Fall Stay That Feels Warm and Welcoming
Staying at the Washington Hotel places you at the heart of the region--surrounded by history, coastal landscapes, and the kinds of small-town charm that encourages lingering a little longer. Whether your perfect fall day looks like a nature walk, a scenic drive, a warm drink in a nearby cafe, or learning something meaningful about this place and its past, the Eastern Shore has something that will stay with you.
We look forward to welcoming you this season.
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