As the calendar slowly slides into fall, what better way to milk out the last few weekends of pleasant East Coast weather than to plot an escape to a waterfront town? St. Michaels, Maryland is a small town (population 1,035) on the state’s Eastern Shore. Just two hours from Washington, D.C. and Baltimore, the waterfront destination has a rich history dating back to an Episcopalian parish formed in 1677.
Today it’s a popular spot for yacht lovers and luxury seekers alike. And if the town rings somewhat familiar to you, that might just be because it is. You’ve seen its top hotel, The Inn at Perry Cabin, as a backdrop in the 2005 hit comedy Wedding Crashers, starring Owen Wilson and Vince Vaughn.
With all of that said, plan your arrival to town early in the day, if you’re visiting on a weekend. St. Michaels is located in Talbot County, right along the main route that people take to drive to Maryland and Delaware’s beaches, so the two-lane highway backs up significantly with traffic on weekend afternoons. Of course, there’s an added bonus to an early arrival — more time to explore! (Though you’ll likely take a car to St. Michaels, do know that Easton Municipal Airport, about 15 minutes away from the city center, offers an option for small private planes and charters.)
Check into the Inn at Perry Cabin, a lovely colonial mansion with 78 rooms, located along a wide expanse of the Miles River waterfront. Originally built as a home for War of 1812 Navy Veteran Samuel Hambleton, the property has operated as a hotel since the early 20th century, including a period of notable ownership by Laura Ashley executive Sir Bernard Ashley. Today, the property still reflects much of its architecture and design heritage; albeit with a more modern and polished feel. Opt to splurge on the “Master Suite,” a spacious two-room, 1.5-bath suite on the ground floor of the hotel that features panoramic water views and a large private terrace. But don’t admire the overstuffed couches and glass-enclosed showers for too long. Borrow one of the hotel’s complimentary bicycles and head into town to start your day.
Begin with a stroll down Talbot Street, the town’s main strip, where you can visit The Christmas Shop, which stocks, as one might imagine, holiday goods, year-round. Then visit The Preppy Redneck, a collection of fun accessories and clothes for the countrified prepster in your life. Be sure to also pop into Guilford & Company, a gem of an antique silver and jewelry shop specializing in pieces from the Victorian period onward. Had you planned your trip for the summer, you could have been a part of “Girl Talk,” the store’s lighthearted weekly chat at the Inn at Perry Cabin where guests learn about the history of jewelry.
After shopping, grab lunch at local favorite Ava’s Pizzeria & Wine Bar, where you’ll find wood-fired pizzas — you won’t go wrong with Meat, Meat & Meat, a hearty pie made with sausage, pepperoni, meatballs and tomato gravy — as well as a special menu for your four-legged companion. “Hammy’s” dog menu includes items such as beef stew and an organic chicken breast in rice and light gravy. As you’ll quickly notice, the walkable town is quite dog friendly.
Trek back through town and take your pick of ways to while away an afternoon. Delight in a stop at the Eastern Shore’s largest winery, St. Michaels Winery. The place offers by-the-bottle, glass and tasting options of a variety of Maryland-grown selections such as MD Chardonnay and Island Belle Sangiovese. Eastern Shore Brewing, situated right next door in a historic mill, pours housemade gems such as St. Michaels Ale. Prefer something harder still? In the coming days, Lyon Distilling Company will become the second whiskey distillery to open in Maryland in over 40 years.
Next, it’s time for a nap – or a massage. If you elect to go with the latter, try a treatment at the acclaimed Linden Spa at the Inn at Perry Cabin or the Aveda Concept Spa at the Five Gables Inn & Spa on Talbot Street in town. Whichever relaxation route you go, be sure to save time to detour to the Inn at Perry Cabin’s daily high tea (3 p.m. to 5 p.m.), a service that comes complete with tea sandwiches, scones and pastries in the hotel’s Morning Room or on the terrace.
For drinks and dinner, pick your choice of fancy or fun. We love three off-property places equally: the 208 Talbot, with its simply prepared steak and seafood menu; the Hunters’ Tavern at the nearby Tidewater Inn,features a local menu of finely prepared American classics such as soft shell crab tempura and Chesapeake gumbo; or the always popular Scossa, which serves Italian fare in a lounge-like setting.
Begin your second day with a short harbor tour via one of the Inn’s kayaks or The Harbor Shuttle. It’s easy to see why so many notable Washingtonians have weekend homes on the Eastern Shore, including former Vice President Dick Cheney, former Secretary of Defense Donald Rumsfeld and Fox News personality Greta Van Susteren.
Stop for lunch at Crab Claw Restaurant in Easton, one of Maryland’s most famous crab houses. Learn how to crack the crustacean — and get schooled on the difference between a male and a female. (FYI: A male, known as a “Jimmy,” has a long inverted “T” on its stomach, while a female, called a “Sook,” has a more bell-shaped marking.)
That afternoon, use your Inn-provided complimentary pass to visit the Chesapeake Bay Maritime Museum, located at the foot of the harbor. Learn the history of the 1879-built Hopper Strait Lighthouse, which is located on the museum grounds. Need more water time? Head out for a sail. The Selina II, built in 1928, is one of the prettiest ships in the harbor and it can be reserved for private excursions and lessons. If you were hoping for a ride on the Woodwind II, the boat featured in Wedding Crashers, you’ll have to head an hour away, to Annapolis. It’s docked there and available for charter.
If you’re lucky enough to have one more night at the Inn, a celebratory dinner at the property’s fine dining restaurant, Sherwood’s Landing, is in order. With a menu so full of delightful options, you won’t know whether to nosh on locally sourced seafood (St. Michaels imperial crab cakes) or wonderfully prepared meats (apple- and chestnut-stuffed duck breast). But whatever dining choice you make, you won’t lose, if for only capturing the dazzling view of Miles River from your table.
Photos Courtesy of Orient-Express Hotels Ltd and Tony J Photography