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 also offered a glimpse of Maryland’s Eastern Shore—a place where madras pants, nautical-themed wedding vows, and jerks named Sack Lodge were completely normal parts of life.
Cue to the real Eastern Shore, a collection of beautiful small towns, quiet peninsulas, vast wildlife refuges, and pristine inlets on the eastern edge of the Chesapeake Bay. And while beach-goers, crab-seekers, and madras pants can be out in full force during the summer months, autumn transforms the Eastern Shore into a beautiful, 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 situated 80 miles east of Washington, D.C. While St. Michaels offers countless bed & breakfast options—such as the quaint Five Gables Inn & Spa—larger groups of long weekenders should consider renting one of the unforgettable waterfront homes available on VRBO.com. 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.
Like A Troubled Bridge Over Troubled Water
What is it that makes the Chesapeake Bay Bridge—the 4.3-mile span connecting the bay’s western and eastern shores—so nervewracking? The flimsy guard rails? The 186 feet between the roadway and the bay below? The fact that this actually happened?
That’s right, it’s all of the above. Therefore, 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 en route to St. Michaels, 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 downtown St. Michaels, a charming collection of restaurants, vacation homes, and gift shops that will keep you busy all afternoon. Peruse casual coastal home décor at American Holiday and original vintage posters at Fine Old Posters—both 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
While cooking dinner at home comes with the added bonus of a sunset-viewing party on the dock, don’t be afraid to go 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).
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 pristine waterfront views—and a delightful bike route from which to view them. 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. Don’t forget to keep an eye open for Dick Cheney and Donald Rumsfeld—the former veep and defense secretary both own homes in the area.
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. However, 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 wedding destination 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 gourmet 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).
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 is home to the largest breeding population of American bald eagles on the East Coast north of Florida. Autumn is a stunning time to visit this 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.
When mealtime rolls around, head back north to Easton, a charming town of restaurants, art galleries and about 15,000 of the Eastern Shore’s luckiest residents. Grab a table at Mason’s, which has been serving Easton’s favorite lunch dishes since 1965. Enjoy succulent crab cakes or an outstanding selection of 20 different sandwiches in this quaint Victorian home-turned-bustling café. Just don’t leave without picking up some handmade chocolates for the road (22 South Harrison Street).
Let the afternoon roll by as you explore the quaint streets of Easton’s downtown. 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, take a few minutes to view some of Easton’s best local landscapes, portraits, and still lifes (5 South Street).
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, Tondin can be found these days in downtown Easton at Scossa, his renowned love letter to northern Italian cuisine (8 North Washington Street). Celebrate the last night of the long weekend with decadent Italian classics, from maltagliati alla Bolognese to risotto with fresh peas and shrimp. Relax and enjoy the splurge, as the sun sets on another long weekend to remember.
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 salad at Ava’s Pizzeria & Wine Bar; a campfire at home | MONDAY: The streets of Easton; Mason’s; the South Street Art Gallery; sunset in Easton.