This quaint, idyllic, 1,000-resident waterfront town on the Chesapeake Bay is a weekender's dream, with stately colonial mansions, quirky dives, and seafaring locals ready to whisk you off on their yacht for the day. If St. Michaels isn't on your radar yet, it should be.
ST. MICHAELS, Maryland — As serial weekenders living in Brooklyn, we know a thing or two about East Coast travels. We’ve explored every Catskills town from Accord to Woodstock, eaten our way through the Berkshires, hopped around Fire and Shelter Islands, and made the most of overnight stays in D.C. and Philly. Yet somehow, Maryland’s Eastern Shore escaped our notice — until the Inn at Perry Cabin invited us down for their annual Return of the Fleet, when their yachts travel back to the hotel to mark the start of the summer season.
Turns out, it’s quite doable for a weekend. A 7 a.m. train had us at the Baltimore/Washington airport before 10, and by noon we were sailing across the Chesapeake Bay on a yacht named Star Light. Our captain, Bud, entertained us with bottomless champagne, the occasional shower of bay water, and quips like “I don’t drink anymore … but I don’t drink any less either.” We soaked up the sun and listened as he and the other locals on board swapped sailing stories and gossip. Apparently everyone on the Eastern Shore knows everyone — and if they don’t, they definitely know that person’s nephew/husband/ex-wife/sister-in-law.
Sailing up to the hotel felt a bit surreal. A bagpiper played on the lawn while guests and locals stood on shore to welcome the fleet and servers greeted us with wine and canapes like we were at a wedding (fitting, given that the inn had a cameo in Wedding Crashers).
With our land legs back under us, we meandered over to Foxy’s, a beachy hangout with a large deck overlooking the marina. It was the season’s opening night, which meant the entire town was out. We recognized a few people from the sail over. They said hello and introduced us around, making us immediately feel like part of the community.
We were told to order Orange Crushes, apparently the Shore’s signature drink, made with vodka, triple sec, freshly squeezed OJ, and Sprite. And then another round, this time “skinny,” which swaps soda water for the Sprite and triple sec (Real Housewives connotation aside, everyone we talked to swore by this variation — and we have to agree). After soaking them up with crab pretzels, we looked out at the sun setting over the water and felt our shoulders relax as we settled into the slower pace of St. Michaels.
Lay of the Land
Once known for shipbuilding and oystering, St. Michaels is an idyllic waterfront town on Maryland’s Eastern Shore. With only about 1,000 full-time residents, it’s a small, close-knit community, but also a popular tourist destination and second-home location given its access to the Chesapeake Bay and proximity to Baltimore and D.C.
The only road through town, Talbot Street, is lined with colorful shops, American flags, and colonial architecture. Head west a few blocks and you’ll run into the Miles River, a tributary of the Chesapeake Bay, and the marina, where hundreds of people park their boats in the summer and hang out at the waterside restaurants.
What to Do
Chesapeake Bay Maritime Museum
213 N. Talbot St., St. Michaels; +1-410-745-2916
The 18-acre museum owns the largest collection of Chesapeake Bay watercraft and is in the process of restoring a last-of-its-kind 1889 bugeye (a large log canoe designed specifically for oystering). Visitors can chat with shipbuilders and view its progress in the working shipyard.
Lyon Distilling Co.
605 S. Talbot St., #6, St. Michaels; +1-443-333-9181
Tour the micro rum distillery with charming co-founders Ben Lyon and Jaime Windon (they’ll make you want to quit your day job and move to St. Michaels). Then head back up front to sample their small-batch spirits — the dark rum pairs well with Pickett’s spicy ginger beer, while Rock & Rum needs nothing more than ice and an orange twist (tastes like a rum old-fashioned).
Carpenter Street Saloon
113 S. Talbot St., St. Michaels; +1-410-745-5111
Better known as C-Street, this beloved watering hole is the place to be on Thursday nights for open mic (locals will tell you to avoid Friday and Saturday). Fit in by ordering a “Bud heavy tenner” — St. Michaels is one of the only places you can get 10-ounce Budweisers.
Talbot Street Shops
The main drag isn’t long, but it’s packed with galleries, gift shops, and antique stores. Pop into Come by Chance for coastal decor, The Preppy Redneck for needlepoint belts and monogrammed totes, and Ophiuroidea for sea glass jewelry.
You can’t be this close to the Chesapeake and not spend an afternoon out on the water. Charter one of the Inn at Perry Cabin’s six luxury yachts or learn how to sail one yourself in as little as two days.
Where to Stay
Inn at Perry Cabin
308 Watkins Ln., St Michaels; +1-410-745-2200
The Inn at Perry Cabin was notable long before Wedding Crashers. Built over 200 years ago as the home of a naval commander, the white clapboard mansion was a farm, a riding academy, and a six-room inn before Sir Bernard Ashley (husband of designer Laura Ashley) turned it into a luxury hotel. It’s since expanded to include 78 rooms, two restaurants, a pool, spa, gardens, tennis courts, and a brand-new Pete Dye-designed golf course.
Minimally decorated with monochromatic colors, dark wood, and subtle nautical accents, the rooms and suites feel modern but still retain some 19th-century touches like fireplaces and paneled walls. Many also open out onto private balconies or spacious terraces with views of the Miles River.
Purser’s Pub is the inn’s more casual restaurant, serving upscale bar snacks like crab cakes and devils on horseback in a tavern-esque space. Stars is the fancier option, with white tablecloths and floor-to-ceiling windows. For the price, our meal at Stars didn’t blow us away, but its new summer menu (crispy blue crab with green tomatoes, house-made agnolotti with fava beans and wild mushrooms, suckling pig with wild ramps) might just warrant a return trip.
Outside, clusters of Adirondack chairs are scattered throughout the manicured lawn, the perfect spot for a sundowner overlooking the bay and fleet. On cooler nights, grab a spot at one of the fire pits before heading in for a turndown chocolate-chip cookie.
Where to Eat
Foxy’s Harbor Grille
125 Mulberry St., St. Michaels; +1-410-745-4340
With its bright umbrellas, plastic chairs, and Key West feel, Foxy’s seems like the sort of place Jimmy Buffett would dock at.
208 N. Talbot St., St Michaels; +1-410-745-3838
Ask anyone where to eat and they’ll tell you 208 Talbot. And for good reason — it might just be the best restaurant in St. Michaels. Be sure to make a reservation.
Ava’s Pizzeria & Wine Bar
409 S. Talbot St., St. Michaels; +1-410-745-3081
If you need a break from crab cakes, head to Ava’s for house-made meatballs and an onion tart (caramelized onion, gruyere, and crème fraîche).
106 N. Talbot St., St. Michaels; +1-410-745-0404
This sweet little ice cream parlor has been a St. Michaels staple for 31 years. In addition to classics like pistachio and cookies ‘n’ cream, the shop whips up fun, rotating flavors like brown butter peanut butter pie and Saturday Morning (Fruity Pebbles and lemongrass-infused ice cream).
Plan Your Trip
How to Get There
Fly or take Amtrak into Baltimore/Washington International Thurgood Marshall Airport (BWI). From there, St. Michaels is 90 minutes by car. If you want to avoid getting stuck in summer traffic on the Chesapeake Bay Bridge, opt for the Inn at Perry Cabin’s Skip the Bridge package. The hotel will arrange transportation to or meet you at Pier 7 Marina, where you’ll board a 55-foot Hinckley yacht and sail to the inn.
What We Would Do Next Time
Two nights was a perfect amount of time in St. Michaels, but next time we’d go for longer and spend some time on Tilghman Island, one of the last working watermen’s villages in the Chesapeake Bay. Just south of St. Michaels, it’s a low-key, three-mile-long island where life revolves around eating crab and hanging out on the water.
The town is super walkable, and the Inn at Perry Cabin also has bikes on hand. If you want to explore neighboring towns like Easton or Oxford, you’ll probably want to rent a car.
When to Go
High season is May through October. We suggest going in spring or fall when the crowds (and traffic) are a little lighter and the weather is cooler.