Why St. Michaels, Maryland, is the New Under-the-Radar Winter Destination

An alternative to The Hamptons, Maine, and other East Coast seaside escapes, Saint Michaels, Maryland is an under-the-radar waterfront destination ideal for travelers looking for a quick getaway to truly relax and unwind this winter. step back into 19th century ambience, but with 21st century conveniences. Saint Michaels, Maryland, steeped in the region’s crabbing and oystering traditions, is just a quick 90-minute drive from Washington D.C. and Baltimore and easily accessible via AMTRAK from Boston, NYC and Philadelphia, United States.

Nestled along the Chesapeake Bay, Inn at Perry Cabin is the region’s only luxury resort grounded in elegance and a celebrated nautical identity. The quintessential essence of Maryland’s Eastern Shore Brewing is evident throughout the boutique estate, overlooking a picturesque winter-on-water backdrop.

Below is an outline of a weekend itinerary at the Inn at Perry Cabin — from delicious twists on traditional dishes (from lobster roll to a crab roll) and cocktails to a day in Saint Michaels, Maryland or a simple R&R at the Inn for a snowed “Inn” retreat.

Day 1 — Arrive to the Eastern Shore
* Arrive at Inn at Perry Cabin where the rooms and suites have all the charm and character expected from a hotel that came to life just after the War of 1812. A hidden gem situated on 26 acres of farmland along the Miles River, Inn at Perry Cabin now embodies the true essence of a luxury resort.

  • Culinary adventure begins at the award-winning STARS, where Executive Chef Gregory Wiener introduces Chesapeake Bay cooking beginning with the day’s catch — fresh rockfish, flounder, crab, and oysters (in peak season now through early spring) — and pairs it with seasonal vegetables picked from the inn’s garden or neighboring farms.

Day 2 — Bike & Brew
* While overlooking the sunrise over the Miles River, enjoy a quiet morning with breakfast in bed and indulge on fresh crab benedict or the savory-and-sweet zucchini pancakes.

  • Throw on a fuzzy scarf, hop on a complimentary bike and head to the charming town of St. Michaels, Maryland for a visit to the Chesapeake Bay Maritime Museum to learn more about the region’s history and dedication to preservation of the entire region. Take a stroll through town and pop into the eclectic boutique shops and waterfront restaurants serving for home décor, clothing, jewelry, and more. Or choose to take a nearby day trip to Easton, the area’s restaurant epicenter.
  • For an afternoon pick-me-up, visit Lyon’s Distilling Company for rum tastings or St. Michaels Winery, a local winemaker featuring 18 different wines, a tasting room and retail shop.
  • Back at Inn at Perry Cabin, cozy up next to the fire with the new seasonal Rum Winter Coffee featuring Amaretto Disaronno, Bailey’s, and rum from Lyon’s Distilling topped with a smore-inspired combination of graham cracker mix, torched marshmallows, chocolate shavings.
  • For an intimate, casual dinner, enjoy Maryland’s twist on comfort food at Purser’s Pub with dishes including the molten Crab & Spinach Dip, Roasted Harris Creek Oysters with Fresno chili and charred kale, followed by the Chesapeake Bay Crab Cake. Finish the night off with a sweet treat: the seasonal Smith Island cake, a classic dessert originally from the small remote Smith Island, located on the Chesapeake Bay.
  • Join the fastest, flattest 13.1 miles in the mid-Atlantic at the St. Michaels Running Festival. If running isn’t your thing, enjoy biking on scenic trails and streets off Talbot Street. We have a new YMCA, spas, yoga studios, and a Pete Dye golf course. Take a peaceful stroll in our friendly, walkable town, and listen to the church bells at Christ Church St. Michaels.

Day 3 — Stay Snowed “Inn”
* Wake up refreshed and head to a much needed R&R at the Spa at Perry Cabin for a winter retreat with these indulgent treatments focused on renewal and warmth.
o A skin nourishing treatment featuring blend of apple and pear made in-house and used to exfoliate the skin while the heated body wrap replenishes the body of lost minerals.
o Natural Microderm Facial
The Spa will launch new enhancement treatments including targeted CBD application, patchology, and other treatments incorporating natural ingredients such as ruby crystals, mint, coconut milk, and other seasonal botanicals.

  • As snow blankets the region, spend the afternoon curled up by the fire with a favorite book, or enjoy the daily activities offered at the Inn including whiskey tastings, simulators at Inn at Perry Cabin’s golf course LINKS, cell photography classes, paint & sip, and more.
  • Before heading home, book a return trip to Inn at Perry Cabin. Spring is just three months away: the daffodils are in bloom, the tennis courts are open, and the sailboats are back in the water.
    o April marks the Return of the Fleet, a seasonal welcoming of the sailboats as they return to Inn at Perry Cabin and kick-start the spring and summer season on the Chesapeake Bay.