Boats sit in the harbor of St. Michaels, Maryland at sunset

St. Michaels, Maryland: An Historical Day Trip

Boats sit in the harbor of St. Michaels, Maryland at sunset

St. Michaels, Maryland: An Historical Day Trip

A 90-minute drive from Baltimore brings you to St. Michaels, Maryland, a historic and scenic town for boating, fishing, and more.

Driving just a short 90 minutes from Baltimore takes you to St. Michaels, Maryland, a quaint fishing and crabbing town that makes you feel like you traveled back in time. It’s a great place to enjoy a day away from the hustle and bustle of the city. Immerse yourself in the fascinating history, culture, and nautical lifestyle of Chesapeake Bay, the largest estuary in the United States.

With its restored historic homes and picturesque streets, St. Michaels creates a sense of a far more tranquil pace from the moment you arrive. Famous historic sites, such as Chesapeake Bay Maritime Museum, fresh seafood restaurants, and a bustling harbor offer plenty of opportunities for a relaxing visit.

Historic Town

St. Michaels dates to the mid-1600s and is one of the oldest towns on the bay’s eastern shore. It served as a trading post for tobacco farmers and trappers and later became famous for defeating a British attack during the War of 1812. According to the story, the townspeople learned of the impending attack and dimmed the lights in their homes and hung lanterns high in the trees beyond the town, causing the British to overshoot and cause little damage. The single home hit – 200 Mulberry Street – is known as “Cannonball House.”

Nautical History

St. Michaels’s top attraction is Chesapeake Bay Maritime Museum, dedicated to preserving the nautical traditions of the Chesapeake Bay region. The museum sits on 18 acres directly on the water, with a large display of floating watercraft and an ongoing live demonstration of authentic boat craftsmen at work restoring vessels.

“We are noted around the world for our boat restoration and for the largest collection of Chesapeake Bay watercraft in the world,” says Tracey Johns, vice president of communications for the museum.

The 12 buildings include displays of the first English explorers and the diverse activities of bay watermen and boat builders. Other interactive exhibits highlight recreational aspects of the bay, including sailboat racing and tourism, and show what crab picking was like at one of the large seafood packing factories in town.

The museum maintains an impressive collection of 85 boats, including gun runner boats and boats handmade from logs. Climb the steps to the top of the Hooper Strait Lighthouse on the grounds to enjoy spectacular views of the Bay.

Lighthouse in St. Michaels, Maryland

Activities On and Off the Water

After visiting the historical displays, get some genuine nautical experience by taking a harbor tour or sailing on a historic boat. St. Michaels offers many boating opportunities, including fishing, kayaking, and sunset and moonlight cruises. The summer months feature additional festivities, including special festivals for classic boats, wine, running, and coastal sea glass.

If you’re interested in other facets of the town’s history, visit Christ Church on Talbot Street. Built in 1672, the church offers a tour that includes silver baptismal and communion gifts from Queen Anne that date back to the early 1700s.

Watch a sunset, walk along the Miles River, shop in some of the boutique gift shops, and stay in a historic bed and breakfast inn. Accessible by water and by land, St. Michaels Harbour Inn, Marina & Spa offers a taste of everything with waterfront rooms and suites, delicious casual and fine dining, and deluxe spa services, such as coconut papaya facials and bamboo and heated stone massages.

Chesapeake Bay Cuisine

A visit to St. Michaels isn’t complete without dining at one of the town’s exceptional restaurants. From cafés on the harbor to crepe stands and bistros, St. Michaels’ eateries provide numerous highly rated options for every palate. Blue crabs and soft shell crabs are served fresh at many restaurants, and crab cake sandwiches and platters are regional specialties. To try the best of these dishes yourself, visit The Crab Claw, a local favorite since 1965.

Crab cakes on a plate with garnish and raspberries at a restaurant in St. Michaels, Maryland

If you need some refreshments during the day, sip wine at St. Michaels Winery, the largest in the region, or enjoy a cold brew at Eastern Shore Brewing Company, a microbrewery that offers tours. For something a bit stronger, Lyon Distilling Company uses local craft ingredients and aging techniques to create delicious spirits.

Memories of your visit to this quaint town on Chesapeake Bay will stay with you all the way back to Baltimore. Share photos of your day trip to St. Michaels with us on Instagram.