- Located off Eastern Bay, on the upper Miles River
- Established in 1677
- Beautifully Victorian downtown district stayed intact by fooling the British in the War of 1812
- Home to the Chesapeake Bay Maritime Museum
What Makes It Unique
In the early 17th century, St. Michaels harbor was 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 became a profitable mainstay, accounting for many of the fast schooners (eventually known as Baltimore clippers) that plied the seas as well as the many fine homes that continue to be the pride of St. Michaels. 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 visitors with the accumulated charm of that colorful past. The small town offers a big town’s variety of shops, restaurants, B&Bs, an elegant resort and a fantastic maritime museum focused on the Chesapeake. 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, which is a couple of short blocks from the harbor’s plentiful docking options.
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.
St. Michaels is approximately 12 miles west of Easton. From Route 50, take Route 322/Easton Bypass to Route 33, which goes through the heart of town.
Chesapeake Bay Maritime Museum’s marina is ideally located, with 55 slips and services including electric, pump-out, bathhouse and loaner bicycles. You must be a museum member to dock, and dockage fees are additional. Household-level and above members can dock hourly, while Mariner membership or above is required for overnight.
Higgins Yacht Yard and Marina is St. Michaels’s original harbor port, and still a working yard. It’s small with just 30 slips that fill up fast, but it’s a good choice if you are looking for a great location and a basic marina at a good price.
The highly regarded St. Michaels Marina has everything you need for a week, from in-slip fueling and pump-outs to two restaurants (longtime favorite Foxy’s Harbour Grille, and the new Blu Miles Seafood & Grill, with its cheery dockside patio), a pool and a fleet of electric Gem cars for rent. They give extra attention to service with their “yacht butlers” who act like hotel concierges, and they can handle boats up to 220 feet.
St. Michaels Harbour Inn Marina and Spa is part resort/part marina, with 52 transient slips, a 52-room inn and day spa, two waterfront decks at Harrison’s Harbour Lights Restaurant, and a seasonal outdoor pool. The additional resort fee gets you access to the resort amenities including workout room and pool, plus car service and loaner bicycles.
Generally speaking (and depending on weather), anywhere in the broad harbor entrance out of the channel works. The holding is good, though with all those boats you’ll want to be extra sure the anchor is well-set. Inside the harbor, you may 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.
STAYING ON LAND
St. Michaels is one of the most popular destinations on the Eastern Shore, with a bevy of charming inns, B&Bs and the like. Inn at Perry Cabin is one of the best-known resorts on the Bay, and with good reason. A member of Historic Hotels of America, the inn hugs 26 acres of gardens, lawn and shoreline right by town. Amenities include luxury rooms and suites, a pool, croquet lawn, a top-notch spa and a Pete Dye golf course. Dinner at STARS is as elegant as you’d expect, while cocktails around the firepit feels like being home. For historic charm, you can’t beat Old Brick Inn or The Parsonage Inn. The former is a collection of three 19th-century homes that have been turned into a 20-room inn, with updated amenities including Jacuzzi tubs. The latter is an architecturally unique, red-brick Victorian with eight period rooms (three with fireplace). The Wildset Hotel is the newest kid on the block, opened in 2020. Like many historic inns, it’s set in four 19th-century buildings but the interiors are luxe and modern, with chic style that blends old and contemporary. Add in fantastic dining at Ruse and you have a new classic in town.
EXPLORING BY WATER
If you’re trailering in, there are public boat ramps right in town, opposite the town dock and just before St. Michaels Harbour Inn and Marina. For kayaks, canoes and SUPs, drop in at the town dock. Need to rent? Shore Pedal and Paddle has single and tandem kayaks and SUPATX SUPs (plus hybrid and cruiser bikes), all for rent by the hour, day or up to a week. The shop is on Talbot Street but they’ll bring the watercraft down to the water for you.
The Miles River makes for a very pleasant cruise, meandering through the Eastern Shore countryside for several miles. We’re particularly fond of little Hunting Creek, with its tidy farms and striking architecture upstream. But the real treat within easy distance is the Wye River, whose entrance lies less than four miles from the boat ramp. Take the eastern branch for a ride through 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. Take the time to go ashore at Drum Point and explore this preserve. Be aware that there’s a low bridge at the far end of the island that connects with the mainland.
Paddlers 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 2½ miles.
For a different experience, head down Chew Ave. 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.
If you want someone else at the helm, here are three ways to go. The skipjack H.M. Krentz was built in 1955 in Harryhogan, Va. She heads out on Saturday sails from the Chesapeake Bay Maritime Museum, offering a look at the lives and work of oystermen. 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. Families will enjoy the 70-minute narrated tour on Patriot Cruises’ replica 1930s steam ferry, which takes you out in the Miles River and shares the fascinating history of this port town.
EXPLORING BY LAND
Start at the Chesapeake Bay Maritime Museum, knowing that it might take you all day, or even a weekend. The motto at CBMM is “Please DO touch!,” a welcome change from the standard museum “don’t touch!” warning. Visit the shipbuilding area and ask all the questions you want about this artful trade. Then wander through the large collection of Chesapeake Bay craft. (Some of the smaller ones are available for rent.) Climb up the old Hooper Strait Light and discover how lighthouse keepers lived while you take in the sweeping view of the harbor. 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. End the day with a ride on the museum’s 1920 buyboat, Winnie Estelle.
The Classic Motor Museum is an easy walk from the Maritime Museum, with exhibits spanning three historic buildings. In the Exhibit Barn you’ll find antique motorcycles, a 1917 Maxwell touring car and a climb-aboard, 1931 La France firetruck. The display is small but ever-changing, as collectors and car buffs lend their cars to the museum on a rotating basis.
Unlike many towns along the Bay, St. Michaels’s Victorian-era downtown is perfectly intact, thanks to some sly deception that misdirected British attacks during the War of 1812—a story cheekily honored today by the plentiful Union Jack flags you’ll find waving in the harbor.
Talbot Street, the main drag, is filled with intriguing shops set inside restored buildings, while the side streets are a wanderer’s delight, lined with centuries’ worth of cool architecture. And the shopping! Iron Will Woodworks/Reclaimed is filled with one-of-a-kind furniture, vintage neon and loads of architectural and nautical salvage, or do some serous antiquing at Antiques on Talbot, considered one of the best dealers the East Coast. We love to browse the books, gifts and sundries at Pemberton Pharmacy and Gifts, which is also a full-service pharmacy. As for clothes and art galleries, we won’t even start; you’ll enjoy finding your favorites on your own.
Make a fun afternoon or evening in the Old Mill District. Start off at the spirits shop at LYON RUM, adjacent to the distillery where they produce world-class rum. You can also sample Gray Wolf Craft Distillery’s vodka, rye whiskey and gin. The newly renovated distillery should reopen in summer 2022, adding craft cocktails to the samples. Just around the corner is St. Michaels Winery, which uses Eastern Shore grapes to produce both reds and whites, from Oaky Dokey Chardonnay to Maryland Merlot and Gollywobbler Red. Do a tasting, try a flight or get a bottle to enjoy there or to go. Finish up at Eastern Shore Brewing Company, the Eastern Shore’s oldest micro-brewery, which has 10 beers on tap, plus darts, shuffleboard and live music on weekends. We confess a decided preference for Situation Critical IPA, but you may prefer Back Creek Blonde or even Blue Heron Coffee Porter. (The coffee comes from Blue Heron Coffee, a great java joint next door.) Carpenter Street Saloon has been a town staple since the 1960s. It’s low-key and has something for everyone, starting with breakfast at 8 a.m. up through bar food and bands on weekends, and stays open till midnight. Everyone comes through here at some point and you never know who you’ll see, from duck hunters fresh off the marsh to big-name politicians dressed down for a weekend in the country.
The Crab Claw is one of the Bay’s classic crabhouses, front and center on the harbor in a red former picking warehouse since the 1950s. Come here for fresh steamed Maryland blues, oysters, cherrystone clams and shrimp. They don’t take reservations so put your name in and expect a wait, worth it for the view from the waterfront deck. Been there, done that? Awful Arthur’s Seafood Company is a Virginia-based company known for fresh seafood and an extensive raw bar, best enjoyed at a bistro table on the central back patio. Or taxi out to Chesapeake Landing; located two miles outside of toward Tilghman Island, there’s always a crowd, it’s usually locals, and that tells you all you need to know.
Ava’s Pizzeria and Wine Bar is much beloved for their wood-fired oven and cheery walled garden with retractable roof, perfect for sunny days. Choose from thin-crust or Sicilian-style pizzas with toppings like charred pepperoni, caramelized onion and gruyere cheese. There are 14 wines by the glass, a great selection of oysters, and special menu for pups. St. Michael’s favorite cantina now goes by the name Gina’s Café, but they still have the tasty Tex-Mex tacos, housemade salsa and bean dip that built their avid local following. Margaritas and Old Bay-dusted Shore nachos on the sunny patio is what weekends were made for. If Italian is your thing, head to Limoncello Italian Restaurant & Wine Bar for fresh pastas, gnocchi and risotto, served in a bright, blue-and-yellow space in the heart of town. At Theo’s Steaks, Sides and Spirits the name says it all: hand-carved aged beef and classic cocktails served in a cozy yet handsome setting, and best of all, shorts and boat shoes welcome!
St. Michaels is just 20 miles from the Oxford-Bellevue Ferry, America’s longest-running privately owned ferry. The ride across the Tred Avon River takes about 10 minutes, and is a great way to enjoy a living slice of history. Before you board, explore historic Oxford, whose entire downtown is on the National Register of Historic Places. On the Bellevue side, head to Royal Oak for a meal at T at the General Store, a creative farm-to-table eatery set in a former 1930s grocery.