Back in 2005, Owen Wilson and Vince Vaughn gave us a comedic gem in Wedding Crashers, a tale of two friends’ escapades as they conned their way through nuptial celebrations in and around Washington, D.C. Besides introducing us to Chazz Reinhold, the film offered a glimpse of Maryland’s Eastern Shore—a place where madras pants, nautical-themed wedding vows, and jerks named Sack Lodge were supposedly normal parts of life.

Cue to the real Eastern Shore, a collection of beautiful towns, quiet peninsulas, and vast wildlife refuges on the eastern edge of the Chesapeake Bay. And while beach-goers, crab-seekers, and madras pants can indeed be out in force during the summer, autumn transforms the Eastern Shore into a quiet respite from city life—a perfect place to curl up by the fire as swans, ducks, and geese glide through the water outside your window.

Make your home base near St. Michaels, a colonial trading post-turned-waterfront resort town 80 miles east of Washington, D.C. The town offers countless bed & breakfast options—such as the quaint Five Gables Inn & Spa—but larger groups of long weekenders should consider renting a waterfront home on VRBO. With your very own fireplace, dock, and Adirondack chairs, you’ll be lulled into a state of complete relaxation—even if it’s only for three glorious days.

SATURDAY

Like A Troubled Bridge Over Troubled Water

What is it that makes the Chesapeake Bay Bridge—the 4.3-mile span that connects the bay’s western and eastern shores—so nervewracking? The high winds? The flimsy guard rails? The 186 feet between the roadway and the bay below?

That’s right, it’s all of the above. Thus, you should take the opportunity to reward yourself for the crossing with lunch at The Narrows, a legend among Maryland seafood enthusiasts. With a beautiful waterfront perch just five miles east of the Bay Bridge, The Narrows has been turning out some of Maryland’s best jumbo lump crab cakes and cream of crab soup for over 25 years (3023 Kent Narrows Way South, Grasonville).

Downtown, Everything’s Waiting For You

Continuing along scenic Routes 50, 322, and 33 will bring you into the heart of St. Michaels, a charming collection of restaurants, vacation homes, and gift shops that will keep you busy all afternoon. Peruse coastal home décor at American Holiday and original vintage posters at Fine Old Posters, both of which are conveniently located on the Talbot Street strip. In need of an afternoon pick-me-up? Swing by Justine’s Ice Cream Parlour, home to the best milkshakes in town (106 North Talbot Street).

I Got Two Pear

Although cooking dinner at home comes with the added bonus of a sunset-viewing party on the dock, don’t be afraid to go out for a splurge. A mere ten miles down the road in Easton, chef Jordan Lloyd’s renowned American bistro Bartlett Pear Inn has been luring diners across the Chesapeake Bay since 2009. It may not be easy on the wallet, but this locally sourced menu offers a truly special dining experience you won’t soon forget (28 South Harrison Street, Easton).

SUNDAY

Make Me A Bicycle, Clown!

Fourteen miles southwest of St. Michaels is Tilghman Island, a tiny watermen’s village that was briefly occupied by the British invasion fleet in 1814. Thanks to its position in the middle of the Chesapeake Bay, Tilghman Island offers lovely waterfront views—and a delightful bike route from which to view them. So rent a bicycle at St. Michaels’ TriCycle & Run (929 South Talbot Street) and cruise along Tilghman Island Road, admiring the pine forests, picturesque farms, and nesting bald eagles along the way.

The Cabin In The Woods

After a long day on the road, there’s no better place to rest your limbs than the Inn at Perry Cabin, the luxury colonial resort dating back to 1816. Of course I’d love to recommend spending a night at the inn—as Warren Buffett and Queen Elizabeth II have done—but in the interest of fiscal responsibility, I must restrain myself. Yet there’s nothing stopping you from enjoying a glass of wine on the breathtaking waterfront patio. And for those eager to do a little wedding crashing of their own, this popular venue was the actual filming location for the Cleary reception (308 Watkins Lane).

Hey Mom, Can We Get Some Meatloaf?

As happy hour draws to a close, stroll back into the heart of St. Michaels to Ava’s Pizzeria & Wine Bar, a Talbot Street fixture that serves the best pizzas in town. A favorite among locals and visitors alike, chef-owner Chris Agharabi’s menu also features outstanding pastas, sandwiches, and salads, all in the comfortable, cozy atmosphere of a friend’s dining room (409 South Talbot Street).

MONDAY

Oh Blackwater, Keep On Rollin’

Hop in the car after breakfast to pay a visit to Blackwater National Wildlife Refuge, a 25,000-acre waterfowl sanctuary 40 miles south of St. Michaels. Sometimes referred to as “the Everglades of the North,” Blackwater Refuge contains one-third of Maryland’s tidal wetlands and the east coast’s largest breeding population of bald eagles north of Florida. Autumn is a stunning time to visit the sanctuary, as tundra swans from Canada arrive in early November and migrant bald eagles fly in from the north. Keep in mind an interesting piece of human history as well—this refuge is believed to have been a hiding place for former slaves on the Underground Railroad.

Easton Promises

Let the afternoon roll by as you explore the streets of Easton, an inviting town of restaurants, art galleries, and about 15,000 of the Eastern Shore’s luckiest residents. Don’t neglect the South Street Art Gallery, the shared venture of a guild of local professional artists. Whether you’re in the market for a painting or not, it’s worth a few minutes to view some of Easton’s best local landscapes, portraits, and still lifes (5 South Street).

Mambo Italiano

A native of the Italian Alps, chef Giancarlo Tondin’s career has led him to some unlikely places, from Harry’s Bar in Venice to the Cipriani empire in New York. Today, Tondin can be found in downtown Easton at Scossa, his renowned love letter to northern Italian cuisine (8 North Washington Street). Celebrate the last night of your weekend with decadent Italian classics, from maltagliati alla Bolognese to risotto with fresh peas and shrimp. So relax, unwind, and enjoy this well-deserved splurge.

Photographs

TITLE: Sunrise in St. Michaels | SATURDAY: Sunrise in St. Michaels; a VRBO rental home in St. Michaels; Harley the dog enjoying a St. Michaels rental home; the Bartlett Pear Inn | SUNDAY: Rental bikes for Tilghman Island; the Inn at Perry Cabin; a campfire at home | MONDAY: The streets of Easton; Easton; the South Street Art Gallery; sunset in Easton.