St. Michaels Where Eastern Shore Elegance Meets Chesapeake Fun

See the Bay: St. Michaels

From traders to tourists
Like many Chesapeake villages, St. Michaels was an outpost for traders, trappers, and tobacco growers in colonial times, and then blossomed into a maritime center for shipbuilding and seafood processing. Its name, Saint Michaels, originates from the Episcopal Parish founded there in 1677; since 1986, the Eastern Shore town has been listed on the National Register of Historic Places. Its well-preserved architecture dates to the 1700s and 1800s, and more than 20 structures comprise the historic district. 

Today, many of St. Michaels’s historic buildings are home to modern pastimes: fine dining, art galleries, craft and jewelry shops, clothing boutiques, and more. In the last 30 years St. Michaels has become a Mecca for tourism as visitors arrive year-round by land and water. Well-known travelers are drawn to this unique town, such as James Michener, who lived in the historic district while writing “Chesapeake.” 

St. Michaels offers an eclectic mix of Eastern Shore elegance and down-home fun, whether one is enjoying gourmet fare delivered by a Yacht Butler (concierge service out of St. Michaels Marina) or fresh crabs dockside at a local watering hole. The center of town is home to fine dining and local eateries and just a short walk to water trails for small craft paddlers; about 10 miles away are fishing charters and lighthouse tours based out of rustic Tilghman Island. Visitors to St. Michaels can also explore upscale spa amenities at the Inn at Perry Cabin, a luxury hotel that has hosted foreign dignitaries such as Margaret Thatcher. 

Arriving by boat
St. Michaels is ideal for arrival by boat, as it is situated on the scenic Miles River, about halfway between the Susquehanna source and the Atlantic mouth of the Chesapeake Bay. The town is located at latitude/longitude: 38.7836° N, 76.2222° W on the Miles, east of the Chesapeake Bay. (Tilghman Island is located directly on the Bay.)

Many of the local marinas, such as the Chesapeake Bay Maritime Museum and the Miles River Yacht Club, are private and require advance reservations. St. Michaels Marina is open to all boaters and has 55 transient slips, located on the “town side” of the harbor, walking distance to the town’s center. The marina accommodates vessels ranging in size from 25 feet to 225 feet, with 10-foot-depth of water. Diesel boats can be fueled at the slips. Other amenities include: small-craft rentals, public boat launch, yacht butler, electric-car rentals, refueling facilities, a nearby pool, restaurants, bars, and a ship’s store. 

Boaters can drop anchor in the Miles River or St. Michaels harbor and catch the Harbor Shuttle water taxi into town by calling VHF Channel 71. (Editor’s note: do not expect this service to run on a rainy Saturday when there are only a few vessels in the anchorage! Plan in advance by making a slip reservation or bringing your own dinghy or paddle craft to tie up at the dinghy dock in rain. Also, know that anchors hold well in and just outside of Long Haul Creek, but the water taxi does not travel that far.) St. Michaels also has a harborside gas and diesel dock, convenient driver services, pump-out services, and groceries within walking distance of the harbor.

Paddle the local trails
The public boat-launch ramp is located on North Harbor Road, near the St. Michaels Harbor Inn. Boaters should contact the town for information on parking at the ramp, (410) 745-9535. In addition, St. Michaels has several area public boat launches, and the surrounding Bay Hundred Area has more than 20 recreational boat and paddleboard launch sites. (DNR provides detailed information on Talbot County launch sites for recreational boaters).

Given St. Michaels proximity to lovely, quiet creeks and the Miles River, paddling its water trails is a popular pursuit. There are four paddling routes near St. Michaels: San Domingo Creek, Oak Creek, Miles River, and Leadenham Creek. The trails are not marked, and skilled paddlers are encouraged to review water-trail brochures in advance (find downloadable maps at 

Taste the local beers
If you arrive by boat and need to stretch your legs, make your way down Talbot Street to the Eastern Shore Brewery at 605 South Talbot Street. There you will find daily tastings of year-round beers, such as the St. Michaels Ale, and seasonals, such as the Magic Hefeweizen, all brewed on the premises. Tasting hours are Monday through Sunday, noon to 6 p.m.-ish, Friday and Saturday, noon to 9 p.m.-ish. (We’re not making that up; it’s on the website: 

~By Patricia Dempsey