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Oxford, a charming, tree-lined and waterbound village with a population of less than 1000, Oxford is one of the oldest towns in America and has a long history in maritime activities. Early in the day, you will still find local watermen at the town dock unloading the catch of the day. You can watch the sailboats arriving from all over the bay to dine at the various local restaurants Oxford has to offer.
While other waterfront towns have succumbed to waterfront condos and glitz, Oxford has retained its historic charm. The tourism and leisure activities are fueled by people's desire for quiet charm, fresh air, summer breezes, and a haven from the hustle and bustle of city life.
The picture-perfect town of Oxford is one of the nation’s closest links to Eighteenth century England. Founded in 1683, it was the Shore’s first and only port-of-entry, a bustling village where at any given time up to seven ocean-going ships could be found unloading merchandise from abroad and loading locally-harvest tobacco, lumber and wheat. A few of the town’s most famous early citizens include Robert Morris, Jr., known as the financier of the American Revolution, and Colonel Tench Tilghman, aide-de-camp to George Washington and the man who carried the message of Cornwallis’s surrender to the Continental Congress. Learn more about Oxford's history here.
Today, Oxford is primarily a residential town and yachting haven, with grand historic homes hemmed by picket fences and tree-lined streets. Our advice: park your car and forget about it. The best way to see Oxford is by foot or bike. However, you choose to travel, be sure to take passage aboard the Oxford-Bellevue Ferry, take a moment to catch your breath at the waterfront Oxford Park and its new living shoreline, and explore the 300-year old Robert Morris Inn where James Michener outlined his epic, Chesapeake.
The Oxford Museum and Custom House archive the town’s rich past and the Oxford Community Center’s stage is home to the seasonal performances of the Tred Avon Players. Whatever your preference – waterfront dining or rooms filled with rich history, Oxford’s chefs offer menus that will please every palate.
Oxford is also home to The Scottish Highland Creamery, who just celebrated their 10th year Anniversary, as one of the Top 10 Best Ice Creams in 2015 in the Country by Huffington Post.
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Stay Your Way: Dreamy Stays in St. Michaels & Beyond
Whether you’re planning a romantic retreat, a girls’ getaway, or a solo escape, St. Michaels, Tilghman, and the Bay Hundred area offer a chic and cozy mix of lodging options for every style and budget.
From boutique inns and charming B&Bs to waterfront resorts and private cottage rentals, you’ll find the perfect place to relax, recharge, and wake up to stunning Chesapeake Bay views.
Your dream getaway starts here—book your perfect stay today!
Find the perfect place to fit your needs here.
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Savor the Flavors of St. Michaels: A Foodie’s Paradise
Nothing says Chesapeake Bay vibes like cracking into a steaming pile of locally caught Maryland blue crabs, but that’s just the beginning! St. Michaels is home to an incredible culinary scene that goes beyond seafood—offering something delicious for every craving.
Seafood & Chesapeake Classics
From perfectly seasoned steamed crabs and golden, lump-filled crab cakes to sweet soft-shell clams and fresh rockfish, our waterfront town is a seafood lover’s dream.A World of Flavor
Craving something else? We’ve got it! St. Michaels serves up an eclectic mix of dining options, including:
Steakhouses for the ultimate indulgence
Authentic Mexican bursting with bold flavors
Classic Italian with homemade pasta & rich sauces
Greek & Mediterranean favorites like gyros, fresh seafood, and vibrant mezze platesFind Your Perfect Spot
Whether you’re looking for a romantic waterfront dinner, a lively crab feast, or a cozy spot for cocktails & small plates, St. Michaels has a table waiting for you. Explore our incredible restaurants here!Find the perfect restaurant here.
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Shop, Sip & Stroll: A Boutique Lover’s Dream in St. Michaels
Calling all trendsetters, treasure hunters, and boutique lovers—St. Michaels is your ultimate shopping destination! Wander through our charming, walkable streets and explore a carefully curated mix of stylish fashion, artisan jewelry, home décor, and unique finds you won’t see anywhere else.
Chic Boutiques & One-of-a-Kind Finds
From boho-inspired clothing and handcrafted accessories to coastal home décor and locally made art, our shops are full of pieces that tell a story—just like your next adventure.Sip While You Shop
Take a break at one of our local tasting rooms, where you can indulge in small-batch wines, craft cocktails, and gourmet bites—the perfect pairing for a girls’ getaway or a solo shopping spree.Ready to Discover Your Next Favorite Spot?
Explore our unique shops and boutiques right here in St. Michaels—where every corner holds something special. Come shop, sip, and stay a while!Find our unique shops here.
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Whether you're an experienced kayaker, a day-tripping boater, a sailing novice, a history buff, an avid fisherman, or anyone else who yearns to spend some time on the water, you will find something to do in St. Michaels and Tilghman Island. It's time to get out on the water and enjoy the outdoors! Find your boating options here.
