The image shows a scenic waterfront with boats docked at a marina. There's a large building surrounded by trees and a lawn with white chairs.

The Ultimate Guide to Maryland's Eastern Shore

Published on August 26, 2024

Welcome to St. Michaels, Maryland – a charming waterfront town with a rich maritime heritage and history that dates back to the 1600s. Tucked along the Miles River, the Inn at Perry Cabin offers the perfect blend of elegance and relaxation. Whether you’re a history buff eager to explore “The Town that Fooled the British,” or just looking to unwind, St. Michaels has something for everyone. Ready to explore this Chesapeake Bay gem? Let’s dive in!

Curated by Benchmark Resorts & Hotels, these are the top five activities you won't want to miss during your stay at the Inn at Perry Cabin:

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1. Sail the Chesapeake Bay

Set sail and experience the beauty of the largest estuary in the nation (third largest in the world). The Inn at Perry Cabin offers a variety of sailing excursions aboard its private fleet, from private sunset sails to hands-on lessons with expert instructors. For a truly memorable experience, book a private sailboat and soak up the serene atmosphere of this iconic waterway.

2. Explore the Chesapeake Bay Maritime Museum

Learn about the area’s dynamic maritime history at the Chesapeake Bay Maritime Museum, located just a short stroll from the Inn. With exhibits ranging from boatbuilding demonstrations to historic Chesapeake Bay vessels, this museum offers a fascinating look into the area's past. Kids and adults alike will love the hands-on exhibits and interactive displays that bring the history of the Chesapeake Bay to life.

3. Bike Along Scenic Trails

Discover the charm of St. Michaels with a leisurely bike ride along its scenic trails. The Inn at Perry Cabin provides complimentary bikes for guests, allowing you to explore the town's picturesque streets, parks, and beautiful waterfronts. Don't miss the St. Michaels Nature Trail, a popular route that winds through wetlands, forests and historic sites, offering a peaceful retreat for nature lovers and cyclists alike.

4. Indulge in Eastern Shore Cuisine

St. Michaels is a foodie haven, offering a taste of authentic Eastern Shore cuisine. Enjoy fresh seafood, including Maryland’s famous blue crabs, at local favorites like The Crab Claw or the waterfront dining at Inn at Perry Cabin’s own Stars restaurant. Don’t forget to try local specialties like oyster stew, rockfish, and Smith Island cake, a Maryland classic that’s sure to satisfy a sweet tooth.

5. Relax and Rejuvenate at the Spa

Unwind with a visit to the Spa at Perry Cabin. This serene sanctuary sets a new standard for relaxation and offers an array of treatments designed to soothe the body and mind, from massages to revitalizing facials. Enhance your spa experience with a steam or a moment of quiet in the relaxation room, surrounded by the beauty of the Inn’s gardens.

Whether you’re looking to sail the Chesapeake, explore local history, or simply relax by the water, St. Michaels and the Inn at Perry Cabin provides the ultimate Eastern Shore escape.


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