Hooper Strait Lighthouse at the Chesapeake Bay Maritime Museum (Photo by Eric Detweiler)
There’s plenty to do in St. Michaels, on Maryland’s Eastern Shore, but the most compelling activity might just be enjoying the view. Nestled against the Miles River, a broad waterway that leads to the Eastern Bay of the Chesapeake Bay, St. Michaels was founded in 1778, finding its economic footing through boat building and then through the seafood industry. Today, its easily traversed downtown and residential areas offer an appealing mix of history and geographically inspired shopping. Best of all: With waterfront parks, activities and accommodations, you’re never far from enchanting vistas.
Soaking up the Atmosphere
To appreciate the town’s underpinnings, start at the harborside Chesapeake Bay Maritime Museum, where one admission price grants two days of entry. That extra time is useful, as the 18-acre campus encompasses a bevy of buildings, including a working shipyard where you’re likely to see shipwrights restoring or building boats, a building dedicated to the bay’s waterfowl – whose comings and goings mark the changing of seasons – and the 1879 Hooper Strait Lighthouse, moved from its original location. In the lighthouse, artifacts and documents tell the story of the keepers and their families. Brave the narrow, twisting staircases to reach a panoramic view from the upper walkway.
From the museum, walk toward downtown past Hollis Park, minding the river’s tidal rise that occasionally overtakes pathways.
Must-Sees
Visit 200 Mulberry St., adjacent to Church Cove Park, to see the house where on August 10, 1813, during the War of 1812, a British cannonball crashed through the roof, bounced down the steps, and — according to local lore — was ushered out the front door by a quick-thinking mother holding her infant. Walk across the park and down Locust Street to find a Little Free Library fashioned as a replica of the 1879 Hooper Strait Lighthouse.
Frederick Douglass is a son of the Eastern Shore, having been born Frederick Augustus Washington Bailey in Talbot County, where St. Michaels is located. Today, the St. Michaels Museum at St. Mary’s Square offers a walking tour devoted to Douglass’ life in the town. Request tours in the off-season of November-March via the museum’s website.
Shop
Once on the main thoroughfare of Talbot Street, it’s easy to pop in shops featuring locally made goods or interesting imports. Pemberton Pharmacy lives up to its name with standard drugstore items but also has a variety of gift and play options. Simpatico, just steps off Talbot, is chock-full of Italian specialties, including olive oils, antipasti and wine. Knot All Bad has nautically themed accessories and apparel for men, and the Chesapeake Trading Co. has women’s apparel plus books and home decor.
STARS at the Inn at Perry Cabin (Photo courtesy the Inn at Perry Cabin)
Dine
If it’s sustenance you want, stop at The Galley, named the Eastern Shore’s best breakfast spot by a local magazine, or try the Blue Crab, on South Fremont Street, parallel to Talbot. The Blue Crab has breakfast food as well as wraps and sandwiches. For dinner, Carpenter Street Saloon — known as C-Street locally — has standard pub fare with an emphasis on local crabs. Ava’s Pizzeria and Wine Bar, will satisfy taste buds needing a break from seafood.
For fine dining, Theo’s has an array of steaks alongside local seafood and even meatloaf. Or just pop in for their signature appetizer: a bottle of Veuve Clicquot alongside fries. Just down the road, STARS at the Inn at Perry Cabin has a seasonal prix fixe dinner (reservation required) that features dishes from Executive Chef Gregory James, named 2022’s chef of the year by the Restaurant Association of Maryland. Don’t pass up James’ fresh take on the classic, multilayered Smith Island cake.
Where to Stay
St. Michaels has numerous waterfront options for overnight stays, from traditional bed-and-breakfasts to high-end resorts. The Victoriana Inn, St. Michaels Harbour Inn, Hambleton Inn Bed & Breakfast and Log Canoe Inn are all adjacent to the town harbor, where all manner of sailing vessels come and go.
The Inn at Perry Cabin offers luxury accommodations. Of the inn’s 78 rooms, all but four have water views, and the expansive cove and river frontage is readily enjoyed via Adirondack chairs, fire pits and even enclosed dining spaces, useful during the pandemic but also practical in cooler weather. Guests may enjoy tennis, spa services or free daily activities such as wreath-making, guided painting or glass etching, even how to make a monkey fist — a knot historically wrapped around a weight and used when casting lines from one boat to another or from boat to shore. And every day, there’s a 5 p.m. Champagne toast to good fortune.
Save the Date
Dec. 3, Dec. 9-11: St. Michaels takes two weekends to celebrate the holidays, starting with Midnight Madness on Dec. 3. The annual event spotlights the town’s businesses that stay open late and offer special sales and giveaways. For Dec. 9-11, the town goes big with parades on Saturday morning on Talbot Street and Saturday night on the water, with boats strung with lights.
