Things to Do on Maryland’s Eastern Shore

Coastal towns, fresh seafood, and laid-back adventures along the Chesapeake

Laid-back, scenic, and full of charm, Maryland’s Eastern Shore is the perfect setting for a coastal escape. Explore historic towns, enjoy fresh-from-the-Bay seafood, and discover everything from quiet beaches to winding backroad adventures.

At Still Pond Inn, your stay is more than just a place to unwind—it’s your starting point for exploring the Shore. Whether you’re planning a relaxing weekend, a romantic escape, or a more active getaway, our central location makes it easy to experience the best of the region. From nearby waterfront towns and marinas to hidden gems and scenic drives, everything is within reach—so you can explore freely, at your own pace, and return to a place designed for rest and comfort.

From nearby destinations like Chestertown and Rock Hall to lesser-known local favorites, every outing offers something a little different—fresh seafood, marinas and docks, boutique shops, galleries, and wide-open landscapes shaped by the Chesapeake Bay. It’s a place where plans can be as structured or as spontaneous as you’d like, with each day unfolding naturally based on what draws you in.

Nearby towns and cities

Explore the towns and cities of Maryland’s Eastern Shore, where each community offers its own blend of history, character, and coastal charm. From working waterfronts and historic main streets to vibrant cultural hubs, these destinations reflect the region’s deep roots and evolving identity. Whether you’re drawn to quiet small towns or lively seaside escapes, there’s something here worth discovering.

Chestertown, Maryland

Set along the Chester River, Chestertown is a walkable, waterfront town known for its historic character, local shops, and relaxed pace. Its streets are lined with well-preserved architecture, independent boutiques, galleries, and cafés, creating an inviting place to spend a few hours or an entire day.

The riverfront adds to the experience, with open views, marinas, and spots to pause and take in the scenery. Throughout the year, events and gatherings bring energy to the town, while its connection to a local college community supports a steady mix of arts and culture.