From Bethesda Magazine: Best of St. Michaels
In part one of our Eastern Shore series, check out a culinary and cultural hub
By Melanie D.G. Kaplan
July 13, 2026 5:02 p.m.
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This is the first part of The Best of The Bay July/August cover story for Bethesda Magazine. Stories on Cambridge, Easton, Chestertown and Tilghman Island will be published in the coming days.
About halfway between Washington, D.C., Rehoboth Beach, Delaware, set along the Miles River, St. Michaels beckons weekend visitors. Established in the 1670s as a shipbuilding town, St. Michaels still celebrates its maritime roots at every turn while offering a classy spin on coastal life. (At a bar, you’re as likely to be chatting with a crabber just off their workboat as a magnate just off their yacht.) Of course, there’s no shortage of activities on the water, but one of the town’s charms is that it’s compact and walkable—only about 1.2 square miles—and lovely even for a day trip. The year-round population is fewer than 1,500, but during the water season visitors flock to town to stroll past shops, enjoy live music and explore side streets lined with historic homes.
Best Family Excursion
Seafarers and landlubbers alike will enjoy the Chesapeake Bay Maritime Museum, which recently opened a special exhibition on Frederick Douglass. A longtime favorite activity is climbing the steps of 19th century Hooper Strait Lighthouse for a spectacular view of the harbor. Enjoy a cruise on a historic six-passenger workboat or aboard the 149-passenger Patriot (don’t miss weekend live music cruises), or join a full moon or Saturday guided paddle (rent a kayak or BYO kayak, canoe or stand-up paddleboard). Every Sunday through 2026, children 17 and younger receive free museum admission and free tickets on Patriot narrated historical cruises.
Chesapeake Bay Maritime Museum, 213 N. Talbot St., 410-745-2916, cbmm.org
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Best Land Trail
The St. Michaels Nature Trail hugs the western edge of town and provides a haven for runners, strollers and four-legged sniffers. The flat 1.3-mile paved path runs along an old railroad corridor, through the woods, past farmland and historic homes, and across a covered wooden bridge above San Domingo Creek—a classic spot for sunset viewing. A 1¼-mile trail extension, which will end at Perry Cabin Park, is expected for 2027. If you work up an appetite early, head to Carpenter Street Saloon.
A few blocks from the north end of the trail) for breakfast—one of the locals’ faves. Trail parking is available across the street from the Bay Hundred Community Pool, 911 S. Talbot St., traillink.com
Carpenter Street Saloon, 113 S. Talbot St., 410-745-5111, carpenterstreetsaloon.com
Best Spa, Sailing and Serenity
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The Inn at Perry Cabin, set on 26 acres at the north end of town, is the dog-friendly luxury resort immortalized by Wedding Crashers 21 years ago. Rooms start at about $715 during the high season, but many of the inn’s activities (and hence the elegant grounds) are also accessible to nonguests: the spa; two restaurants; the Stanley Norman, a 1902 skipjack; and the rest of the inn’s fleet (take a sailing lesson or cruise on Five Star, a Hinckley yacht). Complimentary for guests: bikes, kayaks and paddleboards, guided tours on land or water, and workshops, including glass etching, oyster decoupage and monkey knot tying.
The Inn at Perry Cabin, 308 Watkins Lane, 410-745-2200, innatperrycabin.com
Best Analog Reading Spot
You’ll recognize Book Hounds by its hot-pink door and the sense that you’re stepping into a bookworm’s dream. For starters: the resident dog, Willie Nelson, who shares his dog beds with visiting pups; the Alice in Wonderlandinspired mushroom wallpaper and mushroom stools in the children’s room; the pink typewriter; and the comfy chairs and window seats. The 2-year-old shop hosts Silent Book Club on the third Thursday of each month and offers author talks, a writing club, BYO craft nights and book-bedazzling events (decorating covers with sparkly crystals and gems). Don’t miss the bookish-themed candles, temporary tattoos of skateboarding dogs, and curated kitchenware.
Book Hounds, 104 N. Talbot St., 410-745-8070, bookhoundsmd.com or Instagram @bookhoundsmd
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Best way to see St. Michaels
St. Michaels Museum, an all-volunteer museum with programming for adults and children, offers walking tours every Saturday, May through October. Frederick Douglass tours, with stops including the St. Michaels church Douglass attended and the home where he reconciled with his former owner, take place on the first Saturday of each month. (Douglass was born in Talbot County and spent 11 years enslaved in St. Michaels and on nearby farms.) The Historic St. Michaels tour—which stops at watermen’s cottages, the Edward Willey house and shipyard, and the Cannonball House (which was struck by a cannonball during the War of 1812)—is offered on all the other Saturdays each month. All tours are 90 minutes and $15 (free for children younger than 18; adult supervision required), starting at 10 a.m. at the museum; registration is not required. A 37-stop, self-guided walking tour can be downloaded from the museum’s website. For evening tours, check out Chesapeake Ghost Tours.
St. Michaels Museum, 201 E. Chestnut St., 410-745-9561, stmichaelsmuseum.org
Chesapeake Ghost Tours, 443-735-0771, chesapeakeghosts.com
Best Waterfront Drinks
In St. Michaels, a friend quipped, you drink on the water and eat on the street. If that’s true, there’s no better place to imbibe than Foxy’s Harbor Grille. The waterfront eatery offers a trivia night, live music five days a week all summer and a Margaritaville vibe—well past happy hour (margaritas are $6 after 8 p.m. Friday and Saturday). The “street” destinations offer great dining options: Ava’s Pizzeria & Wine Bar for delish pizza and a lovely dining patio; Gina’s Cafe for eclectic and veg-friendly Tex-Mex; and Ruse, a special occasion spot at the Wildset Hotel with an oyster bar, seasonal menu and James Beard Award-nominated chef.
Foxy’s Harbor Grille, 125 Mulberry St., 410-745-4340, foxysharborgrille.com
This appears in the July/August 2026 issue of Bethesda Magazine.
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Originally published at Bethesdamagazine