St. Michaels

St. Michaels is a bustling small, historic town. The main street, Talbot Street, can wear out a nearly-professional shopper and the maritime museum can wear out ardent history buffs. If those don’t fit you, there’re a number of bike routes looping from St. Michaels, as well as numerous festivals and a rocking weekend night-life (during boating season).

Downtown Historic St. Michaels, Marylabd
Downtown St. Michaels

St. Michaels is named for the Episcopal Parish started in 1677. It started as a tobacco and ship building community. The builders specialized in schooners able to outrun Chesapeake Bay pirates and naval vessels. After the need for schooners died out, oystering came to prominence. Once the oystering industry played out, St. Michaels shifted again and is now a popular tourism stop.

It can be a day-trip or fill a weekend. Walking through the shops can take all day, as can the Maritime Museum. The town has crab houses on the water and contemporary urban-eats restaurants along the main highway through town. St. Michaels is home-base for a number of excellent bike routes, as well as kayaking.

The town is on the neck of a peninsula that ends at Tilghman Island.  Much of the town curves around an inlet off Miles River. The other side of the neck touches San Domingo Creek. Both tributaries enter the Chesapeake Bay near St. Michaels. The museum, marinas and crab restaurants are by the Miles River harbor.


The Mill in St. Michaels
Shops in “The Mill.” Don’t let the warehouse-look fool you.

St. Michaels shops are legendary among women who like to “do the boutiques” and have a nice lunch. You’ll find stores in historic buildings along the main road, Talbot Street (Route 33), and down several side streets.

Unlike most Chesapeake Bay towns, St. Michaels shops stay open at least through mid-Winter — when the post-Christmas sales have cleared out inventory. They open again at the start of boating season (March). They don’t all close “off-season,” but many do.

You’ll find unique women’s wear, boating wear, galleries, gifts, higher-end antiques and so on. The list keeps expanding and stores have been moving into historic buildings off Talbot Street. The St. Michaels Mill, a former flour mill & sewing factory, is now a boutique row.


Maritime Museum

Chesapeake Bay Maritime Museum in St. Michaels
Chesapeake Bay Maritime Museum

Many people know St. Michaels has a museum, and have walked by, but have never walked in. It’s 18 waterfront acres of active history. The Chesapeake Bay Maritime Museum contains 12 buildings, including a boatyard where wooden ships are still built and craftsmen are trained to keep the tradition alive.

Lighthouse at Chesapeake Bay Maritime Museum in St. Michaels
Lighthouse at Chesapeake Bay Maritime Museum

It has what looks like a typical marina, but cleated to the docks are historic boats that are still bay-ready. Around the corner is Waterman’s Wharf, a replica of the working wharfs used daily on Tangier Island and other places on the Bay, as well as a 1879 lighthouse that you can walk through.

Boat restoration at Chesapeake Bay Maritime Museum
Restoration of Chesapeake Bay boat underway

The museum estimates a quick walk through takes about 90-minutes, but it can easily stretch into three or four hours once you get caught up in the stories. That happens even for those who don’t much like museums. The exhibits explain the lives of the people in St. Michaels from the perspective of those who lived it.

There is a charge, which may seem pricey to some, but you can leave for lunch in town and return on the same pass. Parking is free and ample. Visiting boaters can arrange to dock at the museum during the day. The scenic waterfront property is also a popular wedding site, as are many places in St. Michaels.

Each month in the summer, the museum features a different festival. The largest is probably the OysterFest. Check the website for the schedule.


Higher Spirits

Brewery (left) & Winery tasting room (right)
Eastern Shore Brewery (left), St. Michaels Winery tasting room (right)
Lyon Distilling Company, St. Michaels
Lyon Distilling Company in “The Mill”

St. Michaels is home to a winery, a brewery and a distillery. All made in the St. Michaels area, but not connected.

St. Michaels Winery has a tasting room in The Mill (609 S. Talbot Street). Nearby is Eastern Shore Brewing (605 S. Talbot Street) specializing in hand crafted beer. The beer is brewed on the premises and can be sampled in the tasting room. Lyon Distilling Company, on the other side of The Mill (605 S. Talbot, #6), is a boutique distiller featuring small batches of unique whiskey and rum. It also has a tasting room.

Boating/Sailing Adventures

St. Michaels has a number of marinas and several charters are available through these marinas. You can cruise on a skipjack, yacht, or a replica of a 1930’s steam ship.


St. Michaels bike trail
Bike trail through St. Michaels

St. Michaels has a rails-to-trails bike route through town, called the St. Michaels Nature Trail. It’s an 1.3 mile asphalt-paved former train route. This route is shared with walkers. You’ll find a parking lot on one end off South Talbot Street, across from the Bay Hundred swimming pool, and another lot at Bradley Park on Railroad Avenue.

Busy rural Maryland state highways tend to have shoulders, making them popular with cyclists. They’re also flat. And in the St. Michaels’ area, the highways go along the Chesapeake Bay and through farmland. Deeper into the rural areas, the highways may not have shoulders but are not too busy with traffic. Here are some suggested bike routes.

Talbot County also has maps of suggested bike routes.

Off the Beaten Path

Old Mill Deli
Old Mill Deli on the edge of Easton on the way to St. Michaels & Tilghman Island, known for great subs, cheesesteak and grinders.

On the way to or from St. Michaels by car, you’ll go by the Old Mill Deli (1021 N Washington St., Easton, MD 21601) with great subs, cheesesteaks and grinders.

It’s a locally owned place with homemade soups, salads and treats in a red nondescript building with just a sign on the back which faces the highway.

Go around front and you’ll find the parking lot and a screened in dining area with mismatched tables and chairs on a cement floor. For a more scenic eating area, try one of the picnic tables on the grass outside.

One of the several bars on the beach at Lowes Wharf Marina Inn, Sherwood, Maryland
One of the several bars on the beach at Lowes Wharf Marina Inn, Sherwood, Maryland

Down the road, about half-way between St. Michaels and Tilghman Island there’s fork in the road that’ll take you to Lowes Wharf Marina Inn (21651 Lowes Wharf Road, Sherwood, MD 21665).

The road dead ends at a huge bar/restaurant surrounded by a large manmade sandy beach. Boats dock on the bulkhead or mooring balls and an area is set aside for swimming. But you have to use the ladder over the bulk head.

Beach & bulk head at Lowes Wharf Marina Inn
Beach & bulk head at Lowes Wharf Marina Inn

Picnic tables and reclining chairs with umbrellas are set up over the sand. They have bands on the weekend and a big fire pit stands by full of wood for the evening partying.

Outside, there’s an area set aside for corn hole and beach volley ball; inside, there’s pool tables. It’s known locally as a “biker bar” but it’s actually a family place and during the day kids are allowed to play in the sand and swim. Be aware, there are no lifeguards and adults do have to keep watch of their children. At night, it’s more of a boaters bar and a local ‘go-to’ party place.