Two Days, Two Eastern Shore Towns: St. Michaels and Easton
View from the 1879 Hooper Strait Lighthouse in St. Michaels
Easton and St. Michaels are two inviting towns on Maryland’s Eastern Shore and the kind of places that, though small, make a quick getaway feel like a true escape. When we're looking for an easy excursion from our weekend base on Kent Island, we head their way to enjoy a relaxing day of sailing, spa visits, boutique shopping, and garden strolls. Both towns offer a delightful mix of small-town charm and upscale experiences, whether you're craving a fresh seafood lunch by the water, browsing art galleries, or just soaking up the history and seaside appeal.
Easton
Where to stay
We recommend staying in St. Michaels and making Easton a day trip. If you do plan to stay in Easton, book The Tidewater Inn in downtown Easton. It’s centrally located, reasonably priced, with an onsite spa, and the option to book in the nearby Tidewater House (more like a B & B a block away) if you want a quieter and more intimate experience.
Places to eat
Have cheese, charcuterie, and wine at The Wardroom. The cheesemonger picks the cheese for you and it’s absolutely spectacular every time. It’s a well thought out platter of rare cheeses, complimented by freshly made focaccia bread and accouterments like grapes, balsamic, and olive oil that we liked so much we bought a bottle from the shop. You can get a glass of self-serve wine or order a bottle that’s served to you at the table. We haven’t stayed to enjoy the fresh pastas also served here, but will return and share photos when we do.
Eat lunch at Scossa - great salads, pasta, and consistently satisfying specials. This is a popular place with a cozy interior and sidewalk patio that fills up - be sure to reserve on weekends.
Try dinner at Bas Rouge, reviewed a few years back by the Washington Post and a relatively reasonable price for a fixed price menu compared to highly rated restaurants in DC.
Things to do
You can walk all of downtown Easton in thirty minutes. A highlight is antique and consignment shopping, especially for furniture - there are many stores to choose from. If it’s Saturday morning, you can also visit the Farmer’s Market.
Walk through one of the local parks with flowering plants, water features, and shaded seating areas for a break from the mid-day sun.
Visit a museum. The Academy Art Museum has free admission, classes, special events, and a kids camp. The museum and gardens at the Talbot Historical Society, open to the public from dawn to dusk and a nice place to bring a book or picnic blanket.
St. Michaels
Where to stay
A new modern alternative to the traditional bed and breakfasts in St. Michael’s is the Wildset. Right on the main road, it has a great gift shop, minimalist finishes and the Ruse restaurant with a smart interior and welcoming front patio.
The Harbour Inn is an alternative if you prefer waterfront. There you can get a marina-facing suite with a sunny deck, while still being able to walk to downtown St. Michaels shops and restaurants.
For a luxury splurge, the Inn at Perry Cabin is expensive but delightful. The spa is outstanding, grounds are gorgeous, and water views abound. If you want to experience the Inn, but not the price tag, stay at one of the alternatives above, but come for the spa or dinner at the restaurant STARS.
Where to eat
STARS: In the Inn at Perry Cabin for an elegant setting and sunset water views beyond the Inn’s lawn. Breakfast, lunch, and dinner are served here (plan for fancier attire if you go for dinner, which features a tasting menu with lots of great land/sea options).
Ruse: In the Wildset, for an amazing raw bar - the oysters and the smoked trout dip are great starters. The restaurant is open for dinner and Saturday brunch.
The Crab Claw: For traditional eastern shore seafood, right next to the Chesapeake Maritime Museum.
JoJo’s: For ice cream after your meal (the coffee flavor is amazing) or Rise Up for local Maryland coffee on your way out of the city with a convenient drive-thru option.
Things to do
Visit the Chesapeake Maritime Museum, a sprawling campus with various structures to learn about the area’s maritime history. A good time for a fall visit is the Oyster Fest in October (fresh oysters battered and fried onsite are delicious).
Shop along Talbot Street. Like Easton, it doesn’t take long to explore all of downtown, with plenty of souvenir shops and antique stores to visit (plus tastings at the St. Michaels Winery.)
Visit the tasting room at LYON Rum, across from the Classic Motor Museum and next door to the winery and cigar shop.
Get out on the water. The Inn at Perry Cabin has a variety of sailing excursions and experiences, including one featuring LYON rum. Sail Selina II has boat trips and tours. Shore Peddle and Paddle rents kayaks, paddle boards, and bikes.