St. Michaels

The Bay’s Lucky Charm

The short answer is: Why wouldn’t you? At least that’s the answer you’d get from two-and-a-half out of every three boaters in the middle and upper Bay. In fact, on any given weekend in summer, you are quite likely to find at least one and a half of those boaters wandering down Talbot Street, shopping, enjoying an ice cream at Justine’s, learning about the Chesapeake at the extraordinary Chesapeake Bay Maritime Museum or lunching on local Maryland crabs. Of all the wonderful weekend destinations you’ll find here in this publication, you won’t find a more popular one than little St. Michaels. Walk down the dock of any Western Shore marina north of Solomons on a Saturday morning and ask whoever you see where they’re headed this weekend and the answer is likely to be St. Michaels. So read on, and you’ll see why.

St. Michaels, with a population less than 2,000, lies tucked inside Eastern Bay on a small harbor on the upper reaches of the lovely Miles River on Maryland’s Eastern Shore. Its peninsula, which culminates in Tilghman Island, is remarkably similar in appearance to its northern neighbor, Kent Island. And both bear an uncanny, and, we may say, entirely appropriate, resemblance to a pair of crab claws. Go ahead, take a minute to pull out a map of the Chesapeake and you’ll see what we mean. Right? Well, St. Michaels is located on the top of the southern claw at about the second knuckle. Don’t worry, we’ll get a bit more specific in the How to Get There section. First, let’s look at how St. Michaels is laid out. 

Early in the English colonization of America, which is to say the 17th century, St. Michaels harbor was chosen as a shipping point for area tobacco plantations. After the Church of England parish of St. Michaels was established in 1677, a settlement sprang up and pretty soon the new town was in business. Shipbuilding soon became a profitable mainstay, accounting for many of the fast schooners—the kind eventually known as Baltimore clippers—that plied the seas and fine homes that continue to be the pride of St. Michaels as well as other Eastern Shore towns such as Oxford and Cambridge on the nearby Choptank River. When the shipbuilding industry faltered, St. Michaels became a waterman’s town, surviving well into the 20th century on the Bay’s bounty of oysters and crabs. 

Now, St. Michaels attracts thousands of visitors every year, by boat and by car, to visit the accumulated charm of all that colorful past. Because the small town offers a big town’s variety of shops, restaurants, beds & breakfasts, an elegant resort, and one of the two best maritime museums on the Chesapeake (the other one is in Newport News). It also offers three fine marinas for easy access from the water. Because it is a small town, St. Michaels is also compact and easy to get around on foot or bicycle. Most of the shops and many of the restaurants are found along Talbot Street, its main thoroughfare, which is a couple of short blocks from the harbor. 

Here is a quick rundown of the harbor. The elegant Inn at Perry Cabin by Belmond, lies on the north end, followed by the and its docks, then the public dinghy dock and the Crab Claw Restaurant. Higgins Yacht Yard lies on the western side, followed by St. Michaels Marina. Just beyond, the town dock and tour boat terminal are located on one side of little Church Cove and the public boat ramp on the other. Finally, St. Michaels Harbor Inn Marina and Spa occupy the harbor’s south end. We’ll talk about all of those later, but now that you know what’s where, let’s look at least at some of the things you are going to want to do during your visit.

If you are coming by boat

St. Michaels is located on the Miles River, an easy 15 miles inside Eastern Bay. There are two ways of getting to Eastern Bay. The first and easiest is through its wide entrance at the southern end of Kent Island. The second is by way of Kent Narrows off of the southern loop of the Chester River. The first is the easiest from anywhere south of the Chesapeake Bay Bridge and the second from anywhere north of that. For Annapolis boaters, it’s a bit of a toss-up. From Annapolis or the Bay Bridge, Eastern Bay is only about 10 miles. From Solomons, it’s a 35-mile trip north. From the mouth of the Bay, it’s a 100 mile journey. But with stopovers in Deltaville and Solomons, it makes an attractive stop on a week’s cruise.

Whichever entrance to Eastern Bay you choose, the trip up the Miles is a quick one. St. Michaels harbor lies on the west side of the river with depths of generally nine to 10 feet. Follow the markers though, because the water is shoal both north and south. Going from north to south, here is the layout. The Inn at Perry Cabin’s expansive property lies to the north, visible even before you reach the harbor. Jutting into the center of the harbor, are the Chesapeake Bay Maritime Museum’s buildings with its landmark Hooper Strait Lighthouse. South of that lie the town dinghy dock, Crab Craw Restaurant and docks, Patriot Cruises and Higgins Yacht Yard. Right next door is St. Michaels Marina, followed by the town docks. Finally, you’ll spot the docks of St. Michaels Harbour Inn and then little Parrott Cove. Chances are that every bit of available space will be filled with visiting boats. The rest will be filled with watermen’s boats and tour boats. There is usually a lot going on in St. Michaels harbor.

If you are trailering in

For those pulling your boat down the Eastern Shore to St. Michaels, you’ll find convenient public boat ramps right in town, opposite the town dock and St. Michaels shuttle boats, off of West Harbor Road, just before St. Michaels Harbour Inn and Marina

Once you launch the boat, you have some lovely cruising ahead of you. The Miles River makes a very pleasant cruise, meandering through the Eastern Shore countryside for several miles. We are particularly fond of little Hunting Creek, with its tidy farms and striking architecture upstream. But the real treat within easy cruising distance of St. Michaels is the Wye River. The entrance to the Wye lies less than four miles from the boat ramp. Take the eastern branch for a ride through an elegant wooded countryside. The river curves around Wye Island,
and if you stay to the left, comes out into Wye North on the other side of the island. You’ll find an excellent place to go ashore and explore this preserve at Drum Point.

If you are launching a kayak, canoe or SUP

The most convenient place to launch your kayak, canoe or SUP is probably at St. Michaels town dock near the Crab Claw Restaurant and the Chesapeake Maritime Museum. There is plenty of parking nearby. You can also put in at the public boat ramps off West Harbor Drive.

Once you’ve launched, you can tour St. Michaels harbor then head out onto the Miles River, turning either north or south as your fancy takes you. The closest creek for exploration is Long Haul Creek, just to the north. If you are feeling adventurous, head directly across the Miles and explore Leeds Creek, which heads into the countryside, with several interesting coves, for about 2 ½ miles.

For a different experience, head down Chew Street to launch at Waterfront Park into San Domingo Creek. There you’ll have plenty of charming coves and bays to explore. As you reach the mouth of the San Domingo, where it empties into Broad Creek, you’ll find a trio of marsh islands, including the largest, but not very large, Hambleton.


We’ve mentioned St. Michaels marinas several times in passing. Here they are with their contact information. Really, you can’t go wrong with any of them. They principally vary in the choice of location and amenities. All are convenient to town. Once again, we’ll take them from north to south.

The first, Chesapeake Bay Maritime Museum’s transient docks, are the only ones that come with restrictions. In order to stay here, you must be a member of the museum. You’ll still need to pay for dockage, but it’s quite reasonable, and admission to the museum is free. Membership also gives you free admission to a number of partner museums.

Next along the harbor is Higgins Yacht Yard and Marina, St. Michaels’ last working yard. This is a good choice if you are looking for a great location and a basic marina at a good price. Higgins, by the way, was recently purchased by Eastern Shore native and nautical engineer Jon Clark, who also sails his family’s classic log canoe, Magic

Farther along the harbor comes the highly regarded St. Michaels Marina, which features in-slip fueling and pump-outs, restaurants—Lighthouse Bar, St. Michaels Crab and Steak House and Foxy’s—a pool and all the usual marina amenities, handling boats up to 220 feet.

Finally, comes St. Michaels Harbour Inn Marina and Spa. The name gives you an indication of its many attractions, with an inn, spa, Harrison’s Harbour Lights Restaurant and pool. There is a daily resort fee of $35 that includes workout room, pool, car service and loaner bicycles, which are handy since the marina is slightly farther from shops and the maritime museum than the others.


If you decide to drop anchor in St. Michaels, one thing is almost guaranteed: You won’t be alone. Anchoring out for a St. Michaels weekend is a favorite way to visit, with upwards of 50 boats on the hook during many weekends.

 Where to go? You’ll see the favorite spots when you arrive, but generally speaking and depending on the weather, anywhere in the broad harbor entrance out of the channel, of course, works. The holding there is good, though with all those boats you’ll want to be extra sure the anchor is well-set. Inside the harbor, you can sometimes find room in Fogg Cove to the north and just inside the cove behind Parrott Point on the south side.

If you don’t want to use your own dinghy to get ashore, call for a water shuttle on VHF 71.

Too crowded for your taste? Use St. Michaels’ back door and anchor in San Domingo Creek. You’ll need to go into the Choptank River, either by taking the shortcut through Knapps Narrows or coming around Blackwalnut Point, and then head up Broad Creek to San Domingo. To get ashore, take your dinghy to the bulkhead next to the dinghy dock and take the short walk into town. This is a good option if you are coming to St. Michaels from the south. If you come by way of Knapps Narrows, watch for traditional shoaling on both sides of the passage. However, the channel was dredged in 2018, so it should be fine for the moment.

In a hotel, inn or bed & breakfast

Towns like St. Michaels were invented for small inns and charming beds & breakfasts. With that in mind, you can understand that we can’t list them all here. Instead, we are going to give you a few of our favorites. We are still exploring and discovering different ones every time we visit. We encourage you to do the same.

Let’s begin at the top of our favorites list, The Inn at Perry Cabin. If you are celebrating a very special occasion with a weekend in St. Michaels, this is the one you may want to consider. The Inn at Perry Cabin may be the Chesapeake’s most elegant address. In fact, it is so elegant that if you don’t want to make the trip yourself, the Inn will send a Hinckley 55 over to Annapolis to pick you up. Really. No matter how you arrive, you’ll find 26 acres of gardens, orchard, and lawn bordering the Miles River. The Inn itself was built in 1816 by an aide de camp of Commodore Oliver Hazard Perry and inspired by Perry’s cabin aboard the USS Niagara. It has since been expanded significantly to a full-service hotel, with a golf course, tennis courts and spa. It frequently ranks as the no. 1 destination for the Eastern Shore. We’ll get to Stars, its excellent restaurant, a little later.

We’ve already mentioned St. Michaels Harbour Inn Marina and Spa, under marinas, but if you want the luxury of sleeping ashore, the Harbour Inn can accommodate you here too. Harbour Inn has 52 rooms and suites, many with a view of the St. Michaels harbor.

Five Gables Inn and Spa is a wonderful spa, but we highly recommend it as an inn as well. The innkeepers have converted three 19th century homes into 20 rooms, each with its own fireplace and jacuzzi. We especially like the fact that they have set aside four rooms and a suite for guests who want to bring their pets. There is also, of course, the spa, indoor pool, and sauna. They even have a needlepoint shop. No roughing it here.

Let’s look quickly at a few other favorites. 

The Two Swan Inn and Cottages is a beautiful renovated and restored inn and several restored cottages, including an old sail shed and watermen’s cottages, that lie along the Miles River within a two-blocks walk of Talbot Street shops and restaurants. Docking is available at next-door Higgins Yacht Yard.

On the north end of the historic district, you’ll find the Parsonage Inn. You can’t miss it, and with eight distinctive rooms and a huge three-course breakfast, you’ll love it!

And last, we have to mention the Old Brick Inn, which is in fact two historic homes and a 20th century New Orleans-style Inn. The two historic homes were built in the early 19th century and make the most of their long history. One of the happiest features of the Old Brick Inn is that one of its elements is the Old Brick Café, which serves an excellent breakfasts. But we’ll get to that in the next section.

Chesapeake Bay Maritime Museum

We have to start here. So should you. And, if you’re visiting St. Michaels with children, you have even more reasons, because the motto at the Chesapeake Bay Maritime Museum is “Please do touch!” rather than the standard museum “don’t touch!” warning. With or without children, this is a museum that wants you to be involved. Visit the shipbuilding area and ask all the questions you want about this living craft. Then wander through the largest collection of Chesapeake Bay craft. Rent one of the museum’s small boats and get out on the water yourself. Climb up the old Hooper Strait Light and discover how lighthouse keepers lived. Take in the sweeping view of the harbor and the Miles River. Feel what it’s like to pull up a crab pot or tong for oysters at the Watermen’s Wharf. Stop by the permanent exhibit and enjoy learning how people have had fun on the Chesapeake for more than a century. Beginning this March, stop by the temporary exhibits and be awed by the photography of Morris and Stanley Rosenfeld in On Land and Sea, A Century of Women from the Rosenfeld Collection. End the day with a ride on the museum’s 1920 buyboat, Winnie Estelle.

Classic Motor Museum

While we’re on the subject of museums, we suggest you drop by St. Michaels’s newest museum, and perhaps the newest automobile museum around. The Classic Motor Museum on Marengo Street is an easy walk from the Maritime Museum and one that will please the car enthusiasts among you. The display is small but ever-changing, as collectors and car buffs lend their car to the museum, then trade them out for another.

If you happen to be in St. Michaels in late September, be sure to drop by the Concours d’Elegance at the Inn at Perry Cabin, where faultless automobile restorations equal the peerless quality of the marques.

Shop Talbot Street

All of us love to while away a few hours studying the window displays of cool little shops in cool little towns, to poke our heads into an antique shop or gallery, looking for the unexpected treasure, to pick out the perfect summer dress or crab-logo polo. Well, St. Michaels specializes in just that kind of lazy-day pastime. From Jimmy and Sooks (with its crab-logo resort-wear) to Olivins’ specialty olive oils to the Chesapeake Bay Trading Co. and Antiques on Talbot, St. Michaels has you covered. We love it! We usually start at the south end of Talbot and work our way uptown, rewarding ourselves at the top with a double-decker ice cream cone at Justine’s. Then we shop our way back down Talbot until we reach the Old Mill District, where we reward ourselves again, this time with an ice-cold St. Michaels Ale from Eastern Shore Brewing Company or a glass of chilled rosé from St. Michaels Winery. But we’ll get to all that, including next-door Lyons Distilling Co. next. (Don’t miss the Iron Will and the Boatyard furniture and antique shops right next to the distillery.)

Keep your “spirits” up

Whether your taste runs to fine rums, dry IPAs, crisp Chardonnays or perfectly roasted coffees, you will want to plan a stop at St. Michaels’ Old Mill District, where you will find all of the above and more. Here’s a sampling:

For locally distilled rums and rye whiskeys, visit the sampling room at Lyons Distilling Co., where Jaime Windon and Ben Lyon are producing world-class spirits. At Lyons, you’ll also find Gray Wolf Craft Distillery, which specializes in vodka and gin.

If you prefer grape-based products, just around the corner you’ll find St. Michaels Winery, which uses Eastern Shore grapes to produce both reds and whites, from Vidal Blanc Reserve and Oaky Dokey Chardonnay to Maryland Merlot and Gollywobbler Red. Tastings are held daily. (; 410-745-0808) By the way, you’ll find more great local wines as well as tasty ciders at Great Shoals Cellars just down the street. Don’t Ginger Hard Apple and Crabapple Imperial sound delicious? Great Shoals also has an interesting selection of sweet wines.

Time to move on to Eastern Shore Brewing Company, the Eastern Shore’s oldest micro-brewery. We confess a decided preference for Situation Critical IPA, but you may prefer Back Creek Blonde or even Blue Heron Coffee Porter.

Speaking of Blue Heron Coffee, you’ll find this excellent small-batch roaster just down the street. Blue Heron specializes in coffee beans grown in the Americas, like Guatemalan Atitlan.

Take a boat ride

Like everything else St. Michaels does, it offers boat rides with flare. No simple tour boats here. Instead you have your choice of a working skipjack, a gorgeous century-old catboat or a replica 1930s steam ferry. How do you decide? We have no idea. We never can, so we alternate one then another from visit to visit. Maybe you’ll have an easier time. Here’s your choice in a little more detail:

The skipjack H.M. Krentz was built in 1955 in Harryhogan, Va., at the Krentz yard. She was restored, and is currently worked and sailed by Capt. Ed Farley, a waterman and boatbuilder instrumental in preserving these iconic Chesapeake oystering craft. Capt. Ed even worked with writer James Michener when he was researching his book Chesapeake.

The impeccably maintained, graceful and glamorous Selina II is a 41-foot gentleman’s yacht built in 1926. She is owned and sailed by Capt. Iris Clarke, the granddaughter of her original owners. A two-hour day sail or sunset cruise will transport you to a more elegant far-away time. Yes, we’re big fans!

If you are in St. Michaels with the whole family, you may want to choose a narrated Miles River tour on Patriot Cruises replica steam ferry. The boat makes two cruises a day on weekdays and four on weekends during the season.

Want to do it yourself? Rent a kayak or SUP from Shore Pedal and Paddle on Talbot Street. As you can tell from the name, you can rent a bicycle here too.

Relax and revitalize at the Spa

Whew, it’s been an exhausting day of non-stop shopping, sampling and boating. Now what? We suggest a few hours of recuperation at one of St. Michaels’ spas. You’ll find not one or two, but three choices for resetting the clock. They are all good and they all have their own personality. We’ll give you the choice, and you make the decision. Here they are:

The Spa at Harbour Inn is located on the third floor of Harbour Inn. Here you’ll find massages and facials like the Thai Herbal Poultice Massage and the Spiced Golden Pear Facial.

Five Gables Spa in the beautiful Five Gables Inn. Here you can get, among other things, a Aveda Hot Stone Massage or a Rosemary Mint Awakening Body Wrap.

Finally, you’ll want to consider Linden Spa at the Inn at Perry Cabin with its steam room, fitness center and facials and massages, like the Compass Energy Balancing Massage and the Tides of the Chesapeake Facial.

Have we mentioned that St. Michaels has an abundance of everything fun? Well, restaurants are naturally a big part of that fun. So here we give you a few of our recommendations. Like everything else, there are plenty more. Bon appetit!


Who can refuse a bacon blueberry waffle? Not us, we love to start our St. Michaels mornings at the Old Brick Inn, where we invariably pick out a dish we never even imagined existed. Like bacon blueberry waffles. Or a spinach bowl, served with eggs, bacon, grilled tomato, with balsamic and sun-dried tomato garlic parmesan olive oil. Don’t worry, you can get simple sausage and eggs too. The Old Brick is also open for lunch Thursday through Saturday.


We have to fit Ava’s Pizzeria and Wine Bar in somewhere, so we’re going to make it lunch, though you may prefer their delicious pizzas and Italian dishes for dinner. Yes, Ava’s serves great pizza, both brick-oven and Detroit deep dish, in every variety you can imagine. Yes, it serves delicious Italian dishes and pastas too. But Ava’s also serves oysters. Raw oysters, wasabi oysters, Oyster Rockafella Pasta and baked oysters in creole butter. Oops, we forgot the wasabi oyster po-boy sandwich. Here’s a tip: Ava’s doesn’t take reservations, so give them a call and they’ll text you when your table is ready.


For that very special night, head over to Stars at the Inn at Perry Cabin. Fresh local ingredients from neighborhood farms and fresh local seafood, simply prepared. Not inexpensive, but impressive.

For every other occasion, we believe you can’t go wrong at any of these, all located on Talbot Street. Theo’s: great for steaks, great for crabcakes, great for cocktails. Bistro St. Michaels: mussels, boar, duck, gumbo, all delicious. And last, but far from least, 208 Talbot: Our favorite is the Asian Noodle Bowl, which includes Maine lobster, Gulf shrimp, local lump crab, Little Neck clams, fresh fish and a lot of delicious complementary stuff, all in a hot and sour seafood broth. ⚓︎