Drive Time: 2 hours, 30 minutes.
It’s tough to find a finer introduction to Maryland’s Eastern Shore than this posh yet understated resort. Fans of the 2005 comedy Wedding Crashers will get a kick out of the fact that the film’s reception scene was shot on the inn’s stunning grounds, taking full advantage of its sweeping views of the Miles River. Once a farm that dates to the War of 1812, the boutique estate is built on 26 acres and offers sailing, golf, tennis and a spa.
Though the inn features 30 suites and 48 guest rooms, the setup is remarkably cozy, with French doors leading to private decks, patios and verandas. Rooms feature nautically inspired interiors and waterfront or garden views. Other amenities include a fitness center, an outdoor pool and bar, kayaking, paddleboarding, bicycles, and more.
Stars Restaurant offers exceptional sustainable Chesapeake Bay cuisine. Selections change daily, but if you’re a crab cake fan and lucky enough to find one on the menu, jump on it. It may be the best you’ve ever tasted. Private dining options are available throughout the property in key locations. And if you’re looking for something more casual, there’s Purser’s Pub, with its locally inspired small plates, impressive whiskey and bourbon list, and inventive cocktails enhanced with cuttings from the inn’s herb garden.
Guests can also dine at the Commodore’s Grill at the Links at Perry Cabin, the resort’s 18-hole championship golf course designed by Pete Dye. And in spring and summer, there’s the High Tide Pool Bar, which offers a small but inventive menu, beer, wine and cocktails, and scoops of ice cream from Oxford Maryland’s Scottish Highland Creamery, an Eastern Shore favorite. Also try the Stanley Norman Skipjack Lager, the smooth-drinking fruits of the Inn at Perry Cabin’s partnership with neighboring Eastern Shore Brewing in St. Michaels.
Brews and Boats
Speaking of St. Michaels, the exceedingly quaint and historic Eastern Shore town is just a short walk from the resort. On June 8, the St. Michaels Brewfest offers an array of specially crafted regional and national beers. Spend the afternoon strolling among various vendors as you enjoy fresh pours and live music at three different venues, each offering live music.
At the 36th annual Antique & Classic Boat Festival and Coastal Arts Fair June 14-16, wooden and fiberglass classics, vintage racers and other antique vessels return to the Chesapeake Bay Maritime Museum, which is adjacent to the Inn at Perry Cabin property. The Father’s Day Weekend tradition is one of the largest classic boat shows in the Mid-Atlantic region.
Mollusk fans can do worse than grabbing a stool at the oyster bar and watching the friendly shuckers do their thing at Ruse, which opened at the boutique Wildset Hotel in 2021 to rave reviews. It’s well-curated selection of oysters sourced from the Eastern Shore and other American waterways is worth the trip alone.
June Rates: Starting at $665.
308 Watkins Lane, St. Michaels, Maryland, (888) 805-8885, innatperrycabin.com.
Related: Pheasant Run Farm Bed & Breakfast Is a Sweet Retreat in Lancaster
