Weekending in St. Michaels

This tiny Maryland town is a beach-hater’s waterfront getaway. 

The Selina II at sunset / Photograph courtesy of Sail Selina St. Michaels

Two hours flat from Philly, the historic hamlet of St. Michaels, Maryland — where the church is older than the Constitution — is decidedly not a beach town. Instead, it’s flanked on either side by harbor and waterfront properties, making it the perfect overnight getaway for the water-loving-but-sand-hating summer vacationer.

Where to stay

For laid-back elegance in historic surroundings, check into the Wildset, a boutique hotel that opened in 2021. Rooms are cozy and minimalist, and the B&B-style breakfast of good coffee and better baked goods will get you going before you take the hotel’s bikes for a spin around town. For a more upscale experience, reserve a room at the Inn at Perry Cabin, where you’ll find top-notch waterfront views and plenty of activities, from relaxing by the pool — either with cocktail in hand or while indulging in a spa treatment — to the athletic: an evening sail on the hotel’s fleet, a morning kayak trip, or an opportunity to try your hand at paddleboarding.

A deluxe room at the Inn at Perry Cabin / Photograph courtesy of the Inn at Perry Cabin

What to do

Enjoy the sand-free waterfront from every angle: Rent kayaks or paddleboards from Shore Pedal & Paddle (Perry Cabin does have a handful that guests can use), take in a sunset cruise on a sailboat with Sail Selina II, or hop on a bike and traverse the flat road between St. Michaels and Tilghman Island, with glimpses of water all along the way. An afternoon in town offers vacation classics: ice cream from one of several shops (go with Justine’s), a cold beer from Eastern Shore Brewery, and plenty of beachy shopping for everything from antiques to clothing.

Dinner at Ruse / Photograph by Cecile Storm

Where to eat

The Wildset’s restaurant, Ruse, is the must-reserve spot, with modern takes on coastal classics. The raw bar offers oysters, ceviche and smoked fish dip, and the menu is fresh and seasonally focused. Bistro St. Michaels feels upscale and friendly at the same time, with French standards like mussels and steak frites or crabcakes for a Maryland twist. For a more relaxed waterfront dining experience, hit Foxy’s Harbor Grill, and ask to sit on the patio. Watch the boats pull in and out of the harbor while you work through as many of the frozen cocktails as possible.

A Quick-Hit Guide to Maryland Crabs

1. Prices are up due to supply, inflation, demand. Expect to pay at least $70 a dozen. Don’t worry — they’re worth it.

2. Don’t bother with small crabs: Anything less than large won’t be worth the time and picking effort.

3. Most reputable spots only sell by the dozen or half-dozen. You’ll want more than you think.

4. The best crab spots won’t have a waterfront view. (Check out Chesapeake Landing Restaurant, just outside Saint Michaels.) Save the ambience for after-dinner drinks.

5.  Old Bay, fries and beer are non-negotiables on your crab-picking table. 


Published as “Jaunt: Weekending in … St. Michaels” in the August 2022 issue of Philadelphia magazine.

Editor’s note: This article has been updated to correct the names of Foxy’s Harbor Grill and Eastern Shore Brewery.