An ideal weekend getaway is a place that transports me from the daily grind. A place where I can both explore and unwind, but still be back in D.C. by Sunday night without feeling exhausted from travel. Eighty miles from D.C. on the Eastern Shore of Maryland — about a two-hour trip give or take traffic — the charming town of St. Michaels offers this respite.
When first visiting the area with my friend Ryan, I rolled my dinged-up car onto the red brick paved driveway leading to the Inn at Perry Cabin, and I began to worry I was out of place. I had envisioned the inn as a quaint lodge. Instead, the tree-lined path led to a 19th-century estate on the water surrounded by lush gardens, tennis courts, a spa and luxury cars. Luckily, the beauty of its exterior was not surface-level. Throughout my stay, the whole staff at Perry Cabin, as well as the people we met along the way, were kind, welcoming and eager to share stories of their historic home.
From food to activities to scenery and history, there is something for everyone. Here’s what to expect when visiting this idyllic town.
The inn’s structure was built based on a U.S. naval officer’s ship cabin from the War of 1812. Commodore Oliver Hazard Perry played a pivotal role in the war and fought off the British from capturing the Great Lakes. Samuel Hambleton served as Perry’s right-hand man and following the war, the government awarded Hambleton a small land grant for his efforts. With the grant, he built an estate and tobacco farm where he grew up in St. Michaels, which would later become the Inn at Perry Cabin. In honor of Perry, Hambleton named the estate “Perry Cabin” with most of the nautical interior resembling Perry’s ship, the USS Niagara. The inn carries a myriad of stories that are as interesting as its founding, including a more recent fact that the “Wedding Crashers” wedding scene was filmed there.
Beyond the inn, the town boasts several free historical stopping points, like a replica small boat from the 17th century. Next door is the Chesapeake Bay Maritime Museum that takes a comprehensive dive into the history of all the type of boats that sailed the bay.
What can easily make or break a trip is the food. It’s one of the first things people ask when they know someone just came back from traveling. Executive chef Gregory James of the Inn at Perry Cabin’s fine dining restaurant Stars does not disappoint. A recent winner of Maryland’s Chef of the Year award, James has a long resume filled with accolades and prestige, including a stint at Jont and working under Marcus Samuelsson. At Stars, he’s developed a sustainable culinary program that focuses on using fine dining techniques and applying them to local dishes and ingredients. He takes painstaking care to build relationships with local fisheries and distributors to ensure quality. Working with the inn’s horticulturist, James has built a garden full of regional ingredients on the grounds.
While walking the docks, we spotted James pulling a crab cage from the water. When the cage reached the dock, it was brimming with blue crabs — the mascot of the region next to Old Bay. The same crabs were then steamed and served imperial style for an appetizer that night. It’s easy to label a restaurant farm to table, but Stars embodies this ethos by taking the extra step and cultivating many of the ingredients themselves.
Similar to their sourcing, the Stars dining experience is just as exceptional. Each dish is crafted with detail and balance. Standout dishes include the Eastern Shore crab dumplings, crescent pan seared duck and the dry-aged mahi mahi. The dry-aged method provides a meatier texture than the otherwise flaky fish texture. It is a Japanese method of curing fish that James is passionate about making more well-known in the States. Staying true to form, the duck and a dry-aged fish dish are on the menu every night, but the accompanying ingredients and the type of fish are subject to change based on seasonality.
It is very easy to stay at the inn without leaving the ground. While I strongly recommend exploring the town itself (see below), definitely take advantage of what the inn has to offer for activities, which include morning yoga classes, private tennis lessons, golf, lawn games, sailing trips, a spa and a zero edge pool.
Our favorite part of the trip was wandering around the town. There were many standard tourist gift shops, but also a year-round Christmas shop, a shop focused just on runners and a husband and wife owned apothecary, The Mill, which makes many soaps and salves in-house.
Two additional things became very clear when walking the town’s mile-long strip: St. Michaels loves booze and ice cream. Despite its small size, St. Michaels has four ice cream parlors and a dozen alcohol-based shops. From wineries and breweries to a rum distillery, you can easily find your poison of choice.
We landed on Lyon Rum, which is a millennial paradise, equipped with a pink and turquoise feather collaged wall, gold accents and succulents aplenty. Their coffee rum was a highlight, as well as an elderflower-infused gin they carried from another local distiller, Gray Wolf. The store offers free samples and we left with purchased bottles of both aforementioned, and a nice buzz.
Perry Cabin recently acquired a 48-foot sailboat dating back to 1902, known as the Stanley Norman. Listed on the National Register, it is one of the 35 surviving traditional Chesapeake Bay skipjacks, a style of fishing boat specific to the region. The still functioning ship is currently going through upgrades to accommodate a working bar and space for guests to stand comfortably. By next spring, people will be able to go onboard for a cocktail hour on the water or reserve it for small events.
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