A Weekend on the Eastern Shore
The Eastern Shore lies on the east side of the Chesapeake Bay in Maryland and includes a cluster of towns. During my time down on the shore, I spent time in Easton, St. Michaels and Tilghman Island. The Eastern Shore is located only 1.5h from DC and 2h from Philadelphia — it’s the perfect escape from the to enjoy some good food, relaxation, a slower pace of life and pretty views. Check out the suggestions below for your next getaway to the Eastern Shore.
WHERE TO STAY
There are a range of places to stay on the Eastern Shore ranging from historic bed and breakfasts, modern inns, waterfront hotels to luxury resorts. I chose to stay at The Wildset; an updated contemporary style inn with modern amenities and an on-site restaurant. Ask my friends…this place is basically my personal aesthetic.
The Wildset Hotel
The Wildset Hotel is located down the main corridor of St. Michaels; the property is composed of four nineteenth-century buildings that have been converted into contemporary spaces with modern amenities. The rooms are bright, spacious, minimalist in design and complete with fireplaces. The main building was formerly a schoolhouse prior to becoming this modern updated space featuring a sundry shop of carefully curated goods, bike rentals, an outdoor firepit with nightly s’mores and the restaurant Ruse.
I really enjoyed my stay at the Wildset. It’s my design aesthetic with clean and simple modern rooms. They provide waters and snacks in the room upon check-in as well as a grab & go breakfast in the morning complete with croissants, yogurt, fruit and coffee. I loved coming back each night and spending time at the firepit with a s’mores kit. It’s the perfect relaxation vibe and gives you the opportunity to meet other guests (most of whom were from DC). I also appreciated being grabbing a glass of wine at Ruse and hanging out on the patio or bring it back to my room to relax with the fireplace lit. There are rooms with soaking tubs and seating areas, which are on my wishlist for my next visit!
The Wildset Hotel, 209 Talbot Street, Saint Michaels, MD, thewildset.com
WHERE TO EAT
Ruse is the on-site restaurant at The Wildset Hotel with a menu developed by Chef Michael Correll formerly of Lacroix in Philadelphia and Tagliata and The Elk Room in Baltimore. It’s located in the front of the main building at the Wildset with an outdoor patio seating facing the street and great ambiance. Ruse features a modern take on seasonal local cuisine and an oyster bar as a node to it’s waterside location. I suggest coming for a drink and snack at the raw bar, then enjoying dinner out on the patio.
Ruse, 209 Talbot Street, St Michaels, MD, ruserestaurant.com
Tickler’s Crab Shack & Restaurant
When you’re in Maryland you have to eat crab. It’s a requirement. Maryland is known for it’s blue crabs that have a delicate texture and buttery taste, which can be attributed to Maryland waters. So of course, you have to stop by this waterside restaurant to enjoy the view, the vibes and the crab! There is an indoor and outdoor seating option right on the water. Pop into the bar for a drink first and take it out to enjoy some games on the grounds either pre or post dinner. Or grab a seat in one of the water-facing Adirondack chairs for a peaceful vibe.
Tickler’s Crab Shack & Restaurant, 21551 Chesapeake House Drive, Tilghman, MD, wylderhotels.com
Bonheur Pie & Ice Cream
Bonheur is the French word for “happiness” and man, did they really hit the nail on the head with this ice cream and pie shop in downtown Easton. From the decor to the delicious goodies it’s literal perfection. A rotating selection of four seasonal pies is offered daily both sweet and savory. They offer varied ice cream flavors that rotate consistently — a dozen seasonal flavors are made on-site daily and you can adorn them with fixings such as chocolate pearls.
For an extra special day join Bonheur for Afternoon Tea every Friday featuring assorted pastries and tea sandwiches paired with Parisian Teas and Champagne. Get your girlfriends together and treat yourself to a lovely afternoon!
Bonheur Pie & Ice Cream, 5B Goldborough Street, Easton, MD, bonheureaston.com
Sunflowers & Greens
Sunflower & Greens is located in the center of downtown Easton. It’s a delightful little eatery with white marble countertops and classic European style bistro seating that serves house-made salads, soups, and wraps. It feels like it belongs in the Hamptons with it’s upscale vibe. It’s the perfect spot to get an afternoon pick-me-up after traveling or exploring the downtown.
Sunflowers & Greens, 11 Federal Street, Easton, MD, sunflowersandgreens.com
Do you like French food? Do you want to be treated like royalty? Then you must get yourself to Bas Rouge. Serving contemporary European food, Bas Rouge is exactly what you would expect of a 5-star dining experience New York City. offering an impeccable integration of fine dining, a world-class wine list, and elegant service. The high style and gorgeous interior offer inspiration in one of the Eastern Seaboard’s cultural and historic gems, Easton, Talbot County, Maryland. The dining experience is refined, and the dishes are characterized by their polished adaptation of traditional Viennese and European classics, with ingredients from the finest local purveyors and farms.
Bas Rouge, 19 Federal St, Easton, MD, basrougeeaston.com
WHAT TO DO
Flying Cloud Booksellers
Flying Cloud Booksellers is an independent bookshop offering a curated collection of fiction and non-fiction bestsellers, biographies, literary classics, books about design, food and wine. Being a food lover, I was in awe of the collection of cookbooks to explore. It had a neighborhood vibe, everyone is welcome to hang out and peruse.
Flying Cloud Booksellers, 26 W Dover St, Easton, MD, flyingcloudbooks.com
Pop over to the Wardroom to put together a picnic of delicious snacks and wine. The European-style shop and bistro offers handmade pastas, house-cured meats, and artisanal chocolates from top French chocolatiers. The Wardroom’s menu consists of authentic Italian pasta dishes, cheese and charcuterie plates and antipasto. It’s the perfect stop for some goodies either to enjoy in house or in the downtown square in Easton.
The Wardroom, 103 N. Washington St, Easton, MD 21601, thewardroom.com
Academy Art Museum
The Academy Art Museum is located off the downtown square in Easton, MD. Both and art museum and educational space, you’ll find exhibitions that draw from their collection of over 1,700 artworks from the 17th to the 21st century. Some highlights include works by Ansel Adams, Francisco Goya, Pablo Picasso and Rembrandt van Rijn. Visiting an art museum is always a peaceful moment for me to enjoy something beautiful that also makes me think.
Academy Art Museum, 106 South St, Easton, MD, academyartmuseum.org
Make sure you become a scotch whiskey and champagne connoisseur with a visit to The Stewart. I actually think the Stewart is a little slice of heaven. It’s an intimate bar and lounge featuring Scottish inspired interiors including tartan, paintings featuring the Highlands and a cozy wood-burning fireplace. The bar stocks Single-Malt Scotch whiskeys and vintage Champagnes. I enjoyed treats before dinner that included truffle popcorn and caviar. Sit at the bar and let them guide you.
The Stewart, 3 Federal Street, Easton, MD, thestewart.com
Need an afternoon pick me up? Stop by the Weather Gage; a contemporary new-age coffee shop in downtown Easton. The coffee shop features La Colombe coffees and Mariage Frère teas as well as baked goods from the in-house boulangerie. I don’t know about you, but I can never pass up a coffee shop, especially one as adorable as Weather Gage.
Weather Gage, 7 Federal Street, Easton, MD, weathergagecoffee.com
1879 Cooper Strait Lighthouse
Chesapeake Maritime Museum features the 1879 Hooper Strait Lighthouse, viewable from the various neighborhoods in St. Michaels. It is mounted on Navy Point and is the second lighthouse constructed at Hooper Strait – the first one was destroyed by ice in 1877.
Chesapeake Maritime Museum, 213 N Talbot St, St. Michaels, MD, cbmm.org
Inn at Perry Cabin
Want to dip your toe into some moments of luxury? Then you should stop into the Inn at Perry Cabin in St. Michaels; a historic resort rooted in American history. The Inn is now open again for non-guests, you can schedule a service at the spa or enjoy one of the restaurants on-site as well as the water views of the Chesapeake Bay. During my visit to the Inn, I scheduled a 60-min massage, enjoyed the steam room and lounge before having a waterfront lunch at Stars.
Fun fact: Wedding Crashers was filmed in various locations throughout Maryland. The reception scene that took place here at Inn at Perry Cabin was filmed on our beautiful Pointe overlooking the Miles River.
Inn at Perry Cabin, 308 Watkins Lane, St. Michaels, MD, innatperrycabin.com
After spending three days and two nights in the Eastern Shore, I was surprised by how at-home, but also upscale everything felt. It reminded me a lot of the Hamptons. The dining scene was reminiscent of what you’d find in some major metropolitan areas and the people were amazing. I am looking forward to my next visit!