A boat on display at the Chesapeake Bay  Maritime Museum.

A boat on display at the Chesapeake Bay Maritime Museum in St. Michaels, Maryland. Photo © F Delventhal, licensed Creative Commons Attribution.

Map of Maryland's Eastern Shore and Atlantic Beaches

Maryland’s Eastern Shore and Atlantic Beaches

The historic waterfront town of St. Michaels is approximately one hour (51 miles) from Annapolis (from Route 50, exit on Route 322 and follow the signs for Route 33 to St. Michaels). This charming vintage port is a popular tourist destination and features manicured colonial, federal, and Victorian homes, stunning churches, and a scenic shopping area with specialty stores, restaurants, exclusive inns, and bed-and-breakfasts. Seafood lovers can eat their fill of local crab, fish, and oysters, and those looking to go out on the water can take a cruise or launch a kayak.

St. Michaels was founded in the mid-1600s as a trading stop for the tobacco and trapper industries. The town’s name came from the Christ Episcopal Church of St. Michael Archangel parish that was founded in 1677. The historic center of St. Michaels, known as St. Mary’s Square (between Mulberry Street and E. Chestnut Street), was created in 1778 when a wealthy land agent from England purchased 20 acres and created 58 town lots. Many of the homes in St. Michaels that were built in the late 1700s and 1800s still stand today.

St. Michaels earned the nickname “the town that fooled the British” during the War of 1812, when residents protected their town from British gunfire using trickery as their defense. Warned of a nighttime attack from British barges positioned in their waters, the townspeople strung burning lanterns in the treetops above the town to fool the attackers into overshooting their targets. The plan worked, and only one house, still known today as the “cannonball house,” was hit in the attack.

In the late 1800s and early 1900s, St. Michaels’s economy was primarily supported by seafood processing and shipbuilding. Slowly, toward the end of the 20th century, the town became a popular tourist destination and a weekend getaway spot for Washingtonians and other regional residents.


Historic District in St. Michaels

The charming and historic downtown area of St. Michaels is a cornucopia of churches, colonial homes, shops, restaurants, and galleries. This elegant district is a destination for many tourists and area residents. South Talbot Street (Route 33) is the main artery through town, just a few blocks from the waterfront.

Chesapeake Bay Maritime Museum

The Chesapeake Bay Maritime Museum (213 N. Talbot St., 410/745-2916, daily from 10am, closing varies by season, $13) is an 18-acre learning center for all things Chesapeake Bay. There are 10 exhibit buildings, the largest display of traditional bay boats, and the Hooper Strait Lighthouse built in 1879.

Instead of relying on tour guides or reenactors to teach visitors about the bay, the Chesapeake Bay Maritime Museum offers real people of the Chesapeake who live and work on the bay and share their actual experiences. Examples include master decoy carvers, retired crab pickers, and ship captains. Visitors can also witness a boat restoration in progress in the museum’s working boatyard or climb a lighthouse.

The museum offers scenic 30- to 45-minute cruises on the Miles River on a replica buyboat (Fri.-Mon. at noon, 1pm, 2pm, and 3pm). Buyboats were used to buy catches off waterman’s boats and take them directly to market. Cruises depart from the lighthouse (tickets are sold in the Admissions Building, $10).

Both self-guided tours (by map) and guided tours are available with admission to view the museum’s many exhibits including art and maritime displays. The museum is a wealth of information on Chesapeake Bay history and the people who live there. Learn what it’s like to be a lighthouse keeper or what type of work goes on in a boatyard. This is one of the best places to find out about life on the Chesapeake Bay.


St. Michaels is all about water. Those looking for an upscale sailing adventure can charter the Selina II, a vintage catboat, through Sail Selina (101 N. Harbor Rd., 410/726-9400, Apr.-Oct.). Passengers are limited to just six per two-hour outing and are offered a personal sailing experience/tour through the harbor and on the Miles River. Guests are invited to help sail the vessel or to just sit back and relax. The boat is docked at the Harbor Inn and Marina. Outings start at $65 per person.

Narrated cruises up the Miles River are also available through Patriot Cruises (410/745-3100, early spring-late fall, $24.50). This two-level, 49-passenger cruising boat is climate-controlled and offers 60- to 70-minute tours. It leaves from 301 N. Talbot Street.

If you long to sail aboard an authentic skipjack, the Skipjack H.M. Krentz (800/979-3370, Apr.-Oct. daily, $35) offers two-hour narrated cruises aboard a 70-foot working skipjack from the 1950s. Sailing cruises leave from the Chesapeake Bay Maritime Museum.

Kayaks ($30 per hour), stand-up paddleboards ($30 per hour), and bikes ($10 per hour) can be rented from Shore Pedal & Paddle (store: 500 S. Talbot St., dock: 125 Mulberry St., 410/745-2320). They also offer guided two-hour kayak tours ($75) in St. Michaels Harbor on weekends and by appointment during the week. Bikes can also be rented from TriCycle & Run (929 S. Talbot St., 410/745-2836, Mon. and Wed.-Sat. 10am- 6pm, Sun. 10am-4pm, $10 for 2 hours).


Talbot Street is the place to start your shopping adventure in St. Michaels. For unique gifts stop by The Preppy Redneck (406 S. Talbot St., 410/829-3635), a fun gift shop; NETime Designs (404 S. Talbot St., 410/745-8001) for home decor, gifts, and jewelry; and Ophiuroidea (609 S. Talbot St., 410/745-8057) for coastal-inspired furnishings and gifts.

Information and Services

For additional information on St. Michaels, stop by the visitor information center on the corner of S. Talbot and Mill Street (410/745-0411).

Excerpted from the First Edition of Moon Virginia & Maryland.