Maryland's beloved Eastern Shore enclave, with a glorious waterfront resort and a buzzing downtown, borders on the divine. Here are 10 ways to enjoy this Chesapeake dream town.

By Tracey Minkin
November 29, 2017
The waterfront approach to Inn at Perry Cabin by Belmond
Joe Vaughn/Courtesy of Belmond

1. Rise and Shine

In a bright white cottage in the middle of the Historic District, Agave Arts & Juicing Company is the ideal morning launching pad. Esteemed local roaster Rise Up provides the excellent coffee, and co-owners Alli Ensmenger and Madeline Moffett create a splendid rotation of cold-pressed juices (in returnable bottles), as well as selling a colorful array of fair-trade art and accessories from their far-flung travels.

Alli Ensmenger and Madeline Moffett at Agave Arts & Juicing Company
Chris M. Rogers

2. Know Your Chesapeake: Take 1

Get acquainted with the maritime history and culture of the Chesapeake Bay by spending a full morning (or more) among the historic buildings and boats at the Chesapeake Bay Maritime Museum. The bounty includes an 1879 lighthouse, a collection of small working boats, exhibits on oystering and crab picking, and a waterman’s wharf shanty.

RELATED: Exploring Maryland's Chesapeake Bay

3. Know Your Chesapeake: Take 2

To understand the rich relationship between the bay and the men and women whose lives revolve around it, head out on the water. And there’s no better steward than Capt. Ed Farley, a passionate and articulate oysterman who offers two-hour tours on his graceful skipjack when he’s not hauling.

WATCH: One of Maryland's Best Restaurants is Throwing an Epic Crab Feast on The Inner Harbor

4. Order the Crab

Yes, you can (and should) ask for the local delicacy as much as you can. The crab chowder and cakes at Stars, at the Inn at Perry Cabin by Belmond, are richly packed with jumbo lump meat. At Gina’s Café, the Shore Nachos add crabmeat and Old Bay seasoning to the traditional chips-and-cheese landscape. And with a picking facility right on the property, freshness makes family-owned Chesapeake Landing a local favorite for feasting.

Gina's Café
Chris M. Rogers

5. Shop the Town

The historic downtown’s Talbot Street is lined with linger-worthy stops. For charming homewares and gifts, browse The Preppy Redneck. Antiques and vintage hunters should scout The Shops at Sea Captain’s Cottage. And for fashion-forward clothing and accessories with a whisper of nautical prep, check out Knotty Living.

Drink tokens that pair Lyon Distilling Company and Foxy’s Harbor Grille
Courtesy of Lyon Distilling Co.

6. Drink Rum

Thanks to a creative reuse project right downtown, you can taste beer, wine, and rum without moving your car. So pick your passion, but don’t miss the tasting room at Lyon Distilling Company. Founded in 2012, Lyon is best known for its small-batch, signature rums, but also puts up a fine Maryland rye whiskey.

7. Hit Happy Hour

For the best boating bar experience this side of the Caribbean, pull up to the welcoming dockside party that is Foxy’s Harbor Grille. Drink of choice: Foxy’s Crushes, an icy blend of vodka and juices squeezed behind the bar, topped with a sweet blast of Sprite.

RELATED: 10 Best Small Towns on the Chesapeake Bay

Inn at Perry Cabin by Belmond
Chris M. Rogers

8. Cruise in Style

There’s never been a prettier fleet of sailing and motor yachts than what’s tied up along the dock at Inn at Perry Cabin by Belmond, and the resort has created a vibrant menu of ways for guests to play on these boats, from weekend-long learn-to-sail packages on its sleek Tadorne sailing yacht to captain-chartered cruises aboard classic Hinckleys.

Downtown’s Talbot Street
Chris M. Rogers

9. Stop for Shakes

The “Wall of Shakes”—a collection of dozens of hand-drawn signs—is alone worth a visit to Justine’s Ice Cream Parlor. But the challenge is to pick which one to order among tantalizers like Mandarin, Creamsicle, and Mint-covered Oreo.

10. Check In

Set graciously along the shores of the Chesapeake Bay’s Miles River, the manor-style Inn at Perry Cabin by Belmond plaits the pleasures of the Eastern Shore into a luxurious sailor’s knot, including a waterfront lawn dotted with Adirondack chairs and 78 guest rooms and suites with serene interiors that are as soothing as the watery landscape. Rates start at $240.

Chestnut Street
Courtesy of Long & Foster

Stay for a Lifetime

Find your forever home in the thriving Historic District
Founded by folks making modest livings on the Chesapeake Bay, St. Michaels’s historic homes are delightfully small. On the north side, you’ll find the one-room-wide, two-room-deep, one-and-a-half-story dwellings that are typical of the Eastern Shore. On the south side, look for T- and L-shaped homes with a two-story bay in one corner.
Pictured here: 202 E Chestnut Street, 4 bedrooms, 2 baths for $645,000