The Eastern Shore of Maryland is a haven for food lovers and shopaholics alike. With its blend of charming small towns and coastal beauty, this region offers delightful dining experiences and unique shopping options. From locally owned boutiques to celebrated restaurants, the towns of Easton, St. Michaels, Stevensville, Chester, Queenstown, and Oxford each have something special to offer. Here’s your guide to enjoying the best dining and shopping across these picturesque destinations.
Easton
Easton is one of the Eastern Shore’s cultural and culinary gems. You'll find a mix of fine dining and casual eateries, with many incorporating locally sourced ingredients into their menus. Standouts include Scossa Restaurant & Lounge, which serves up flavorful Italian dishes, and The Bartlett Pear Inn, known for its upscale farm-to-table offerings.
For shopping, Easton’s historic downtown is lined with unique boutiques and specialty stores. Visit Trade Whims for stylish home goods and fashion, or check out Vintage Books & Fine Art for rare and antique finds. The local Easton Farmers Market is a must-visit for fresh produce and handmade goods.
Saint Michaels
Saint Michaels combines waterfront charm with a vibrant dining and shopping scene. Seafood lovers will want to stop by The Crab Claw for some of the region’s freshest crabs. For a more contemporary dining experience, Ava's Pizzeria & Wine Bar offers wood-fired pizzas and an excellent wine selection.
Shopping in St. Michaels is a treat, with its array of small, locally-owned stores. Olivins specializes in gourmet olive oils and balsamic vinegars, while Chesapeake Bay Outfitters has clothing, accessories, and gifts perfect for the coastal lifestyle. Art enthusiasts can explore galleries like The Red Queen Gallery for unique local artwork.
Stevensville
Located on Kent Island, Stevensville offers a mix of dining and boutique shopping. For a memorable meal, check out Rustico Restaurant & Wine Bar, which serves Italian cuisine with a modern twist. If you’re craving seafood, Fisherman’s Inn is a beloved classic known for its fresh catches.
Shopping in Stevensville includes stops at The Painted Oyster, a boutique full of coastal-inspired décor and gifts. Antique lovers will appreciate KENTmorr Antiques, where you can discover one-of-a-kind treasures.
Chester
Chester, another quaint Kent Island town, also offers excellent dining options and shopping experiences. The Narrows, a waterfront restaurant, is famous for its cream of crab soup and picturesque views. Cafe Sado provides a unique menu, blending sushi and Asian fusion dishes.
For shopping, explore My Little Boutique, a charming spot for women’s fashion and accessories. Don't miss Western Tire & Auto’s gift section, which is known for selling surprising and delightful local items in addition to its primary services.
Queenstown
For a mix of luxury shopping and outdoor fun, Queenstown is the place to be. Begin at the Queenstown Premium Outlets, where you can shop a variety of high-end brands at discounted prices. It’s perfect for everything from apparel to home décor.
When it’s time for a bite, head to The Narrows’ sister restaurant, Hunter’s Tavern, for comforting Chesapeake-inspired dishes, or try Queenstown Pizzeria for casual and satisfying eats.
Oxford
Oxford might be small, but it’s packed with character. For dining, don’t miss The Robert Morris Inn, a historic inn featuring elevated cuisine with a nod to regional flavors. Another favorite is Capsize OXMD, offering waterside dining with casual yet creative menu options.
Shopping in Oxford is equally charming. Stop by Mystery Loves Company Booksellers to peruse a selection of literary treasures or drop in at The Treasure Chest for gifts, jewelry, and home accents with a nautical flair.
Dining & Shopping on the Eastern Shore
The Eastern Shore offers more than just breathtaking views; it’s an experience for all the senses. Whether you’re indulging in the latest culinary creations or shopping for one-of-a-kind finds, each town brings its unique flavor to the mix. If you’re considering making the Eastern Shore your home, contact Chuck Mangold. Chuck will help you find the perfect property so you can enjoy all the area has to offer every day.
Chuck Mangold