How to spend a luxurious weekend in St. Michaels, two hours from Philly | Field Trip

Sunset sails. Vintage art. G&Ts on the lawn. Artisanal pie a la mode. Is your interest Chesa-piqued? The village of St. Michaels, on the Eastern Shore of Maryland’s famous bay, has an image as clean-cut and preppy as a mid-1990s Ralph Lauren ad, but there’s also been a new, young energy in recent years. The result is a road-trip destination — only two hours from Philly, without traffic — that offers an alluring balance of rich heritage and 21st-century rizz. In fall, with cooler air, brilliant foliage, and quieter streets, it’s an especially dreamy escape. Drop anchor.

A historic property with origins dating to the early 1800s, the Inn at Perry Cabin wears the nautical history of St. Michaels like a pair of madras-print shorts. It’s luxurious and dignified, but still breezy, with a terrific spa, lovely in-ground pool and marina stacked with sailboats available for private charter or scheduled cruise.

📍 308 Watkins Lane, St. Michaels, Md. 21663

Grab one of the complimentary bikes from the inn (or rent from Shore Pedal & Paddle, which offers mobile delivery) and pick up the Chesapeake Views Trail, which runs about 12 miles along forested rural roads and across the iconic Tilghman Island Drawbridge onto the island of the same name. After absorbing the 180-degree water views from Black Walnut Point, refuel at Two if by Sea, a cute diner where the omelets come loaded with crabmeat.

📍 5776 Tilghman Island Rd., Tilghman, Md. 21671

In Talbot County, water and land are in perpetual conversation with the people who live there. Spread across several buildings (and a working shipyard!) along the Miles River waterfront, the Chesapeake Bay Maritime Museum explores that relationship through various lenses, from ecology and art to crabbing and boatbuilding.

📍 213 N. Talbot St., St. Michaels, Md. 21663

Ten minutes outside St. Michaels, Easton has become the area’s cultural and commercial nexus, its formerly neglected downtown now a buzzy hub of hip restaurants and quirky shops like Flying Cloud Booksellers, where you can pick up a page-turner and scour the collection of original and reprinted vintage posters. Who knew a 1933 French waffle cookie ad was just the thing your kitchen needed?

📍 26 W. Dover St., Easton, Md. 21601

It’s impossible to choose between impeccable house-baked pies (apple, honey custard, berry lemon) and vivid ice creams (maple walnut, black raspberry, coffee toffee crunch) at Bonheur, a dessert parlor whose Parisian-style banquettes and parakeets-and-peonies wallpaper are Instagram-ready. Save yourself the trouble and just order a la mode.

📍 5 Goldsborough St., Easton, Md. 21601

Getting out on the water is nonnegotiable. Climb aboard Sail Selina’s Selina II, a beautifully maintained 1926 yacht, for two Champagne-enhanced hours of cruising. A maximum guest count of six keeps their experience intimate.

📍 101 N. Harbor Rd., St. Michaels, Md. 21663

Natural wines, robust raw bar, crab cacio e pepe, and an epic cheeseburger. … Ruse has the swagger and chops of a restaurant that’s been beamed in from the city. Maybe that’s because Michael Correll, the James Beard semifinalist leading the culinary programming at the Wildset Hotel, cooked in Philly, Baltimore, and D.C. before joining this smart boutique. Don’t miss the Wild Diver oysters, roasted with urfa biber and garlicky breadcrumbs.

📍 209 N. Talbot St., St. Michaels, Md. 21663