A family of four walking and biking on the Rock Hall Loop

If you’re planning a getaway to Maryland’s Eastern Shore, don’t miss the opportunity to explore Rock Hall. This charming waterfront community offers a perfect blend of small-town hospitality and scenic beauty. The team at Osprey Point, an inn, restaurant, and marinas in Rock Hall, highly recommends experiencing Rock Hall’s unique character by taking a leisurely walk or bike ride around “the loop.” The Rock Hall Loop is a 3.2-mile trail that showcases many of the town’s highlights. Here’s a look at what you can expect on the Rock Hall Loop.

About the Rock Hall Loop

The Rock Hall Loop is a flat, easy trail that winds through the town’s main perimeter, making it ideal for visitors of all ages and fitness levels. Whether you prefer a brisk morning jog, a casual afternoon stroll, or a scenic bike ride, the loop has you covered. As you make your way around the loop, you’ll quickly notice Rock Hall’s laid-back atmosphere. The town prides itself on its relaxed pace, encouraging visitors to slow down and savor the experience. 

The loop takes you past many of Rock Hall’s attractions, giving you a great overview of what the town has to offer. Start your journey on Main Street, where you’ll find an array of charming shops and eateries. Some highlights include Grammy’s Goodies, where you can grab a sweet treat on weekends, and The Hickory Stick, which is a unique boutique, among other great stores, restaurants, and more.

The Rock Hall Loop then leads you towards the harbor area along Chesapeake Avenue, one of the most scenic sections of the loop. At the intersection with Sharp Street, you’ll find Waterman’s Crab House, which is a great spot for a waterfront meal consisting of fresh, local seafood.

Continue on to Bayside Landing Park. Here, you’ll have a great view of the water and the boats lining the harbor. If you need to cool down, take a refreshing dip at the pool, which is free to use and open to the public from Thursday through Sunday in the summer months. Another swimming option is also nearby – Ferry Park, also known as Rock Hall Beach. Whether you want to dip your toes in the water, sit down and relax at the pavilion, or enjoy a picnic, Ferry Park has you covered.

As you complete the loop back toward town, you’ll pass by several marinas and the interesting Waterman’s Museum, offering insight into the area’s rich maritime heritage. The Rock Hall Loop finishes back in downtown Rock Hall, where there are many businesses to explore. 

Lodging in Rock Hall, MD

An aerial shot of Osprey PointYou can stay near all that Rock Hall has to offer, including the Rock Hall Loop, when you book your accommodations with Osprey Point. Our inn, restaurant, and marinas aren’t located on the loop but are just a short walk or bike ride away. With three charming lodging options, a deluxe continental breakfast, and on-site amenities like a swimming pool, we have everything the discerning traveler needs for a memorable trip to Maryland’s Eastern Shore.

To stay with us, please make a reservation online or call 410-639-2194 for more information.