St. Michaels is a bustling historic town. The main road, Talbot Street, can wear out a nearly-professional shopper with its blocks of boutiques & specialty shops, and the maritime museum can wear out ardent history buffs.

Enjoy outdoors? St. Michaels is a major boating stop on the Chesapeake Bay. Popular cycling routes loop from St. Michaels, and the town has numerous festivals as well as a rocking weekend night-life (during boating season).

About St. Michaels

St. Michaels is named for the Episcopal Parish in 1677, starting 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.

Walkway across the canal to St. Michaels crab house

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 several excellent bike routes, as well as kayaking.

The Chesapeake Bay Maritime Museum, marinas, and crab restaurants are by the Miles River harbor. The downtown is about two blocks from the waterfront.

Everything is within walking distance.

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.

Shopping in St. Michaels

St. Michaels’s shops are legendary for boutique-ing and a nice lunch with a cocktail. 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, after 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.

St. Michaels Mill shops, just off the main road at the edge of the downtown shopping district

Chesapeake Bay Maritime Museum

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.

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 wharves used daily on Tangier Island and other places on the Bay, as well as an 1879 lighthouse that you can walkthrough.

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.

Historic homes outside the Maritime Museum entrance

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.

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

St. Michaels’ Higher Spirits

Lyon Distillery in St. Michaels, MD
Lyon Distillery in St. Michaels, MD

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

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. Gray Wolf Spirits shares the distillery and makes rye, vodka, gin, and agave spirits (tequila).

Around the corner, on Talbot Street is the winery and brewery.

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.

Boating & Sailing Adventures in St. Michaels

Log Canoe (type of sailboat) race at St. Michaels

St. Michaels has several marinas and fishing or cruising charters are available through these marinas. You can cruise on a skipjack, yacht, or a replica of a 1930s steamship.

Cycling Around St. Michaels

The bike trail through St. Michaels

St. Michaels has a rails-to-trails bike route through town, called the St. Michaels Nature Trail. It’s a 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.

Cyclists on Oxford ferry in Maryland
Oxford ferry, part of the popular “St. Michaels to Oxford” loop

Busy rural Maryland state highways around St. Michaels tend to have shoulders, making them popular with cyclists. They’re also flat.

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 bike routes.

St. Michaels Restaurants

Foxy’s Harbor Grill, a popular stop for locals

St. Michaels goes from a basic boater marina bar with burgers and crab cake to high-end foodie experiences.

The St. Michaels Business Association keeps a list of restaurants in town. Here’s a restaurant list compiled by St. Michaels Tourism association.

Special Events in St. Michaels

St. Michaels has festivals and special events year-round. The St. Michaels Business Association keeps track of upcoming events.

Off the Beaten Path

St. Michaels doesn’t have a beach. But…

Lowes Wharf Marina Inn waiting for people

Down the road, about halfway between St. Michaels and Tilghman Island, there’s a 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. Boat dock on the bulkhead or mooring balls and an area is set aside for swimming. But you have to use the ladder over the bulkhead.

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 volleyball; inside, there are 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, that there are no lifeguards and adults do have to keep watch on their children. At night, it’s more of a boaters bar and a local ‘go-to’ party place.