St. Michaels is a picturesque harbor on Maryland’s Eastern Shore and was named as one of the Top 10 Best Small Coastal Towns in America by USA Today. Its harbor and some homes date back to the mid-1600’s …[read more on StMichaelsMD.org]
The Oaks and St. Michaels are located in Talbot County. Learn more about tourism in the county here.
Carpenter Street Saloon
Carpenter Street Saloon is a staple of St. Michaels. They’ve entertained dignitaries, celebrities, politicians… You name it! C-Street, as they are affectionately called by the locals, prides itself in being the best dive bar … well, anywhere! Enjoy a beer and some food as you listen to great live, local music!
Sail Selina II
Very upscale & exclusive, the Selina II limits her passengers to just 6 guests for an intimate taste of the history of sail. You will be treated to an unforgettable boating experience with Captain Iris Clarke, granddaughter of the original owners. You can arrange for two-hour, 1/2 day, full day, champagne sunset sails, private charters, overnight excursions, birthdays, anniversaries, and engagements.
St. Michaels Winery
The icon of St. Michaels Winery is the Chesapeake Bay Log Canoe sailboat. The historic Old Mill complex where St. Michaels Winery is located is owned and managed by notable log canoe owner and skipper Mr. Tad DuPont, who sails Island Lark. Call the St. Michaels Winery anytime for a private tour of their winemaking space.
Eastern Shore Brewery
Offering beers for every taste including: St. Michaels Blonde Ale, St. Michaels LT, Not So Pale Ale and seasonal beers…Ameri-Hefe & Ameri-Wheat. Stop by the tasting room and sample a few beers.
Sail aboard the oldest working skipjack on the Chesapeake Bay and Tilghman Island’s pride, the Rebecca T. Ruark. Offering flexible times for 2-hour year-round sails. Longer charters are also available and reservations are welcome. Ask about fishing and crabbing charters aboard the working crab boat, Miss Kim.
The Chesapeake Bay Maritime Museum
The place where stories of the Bay and its people come alive! Nine exhibit buildings on 18 waterfront acres, fun-filled festivals, engaging special exhibitions, hands-on boatbuilding classes, and outdoor summer concerts-come for the day, stay for the weekend.
Chesapeake Bay Outfitters
No trip to St. Michaels is complete without a visit to Chesapeake Bay Outfitters, catering to the casual Eastern Shore lifestyle and serving visitors and locals alike for over 30 years. You’ll find an outstanding selection of family footwear, men’s and women’s sportswear and resort wear, fun accessories and St. Michaels Tees & Sweatshirts. Featured casual apparel brands include Fresh Produce, Tommy Bahama, Columbia Sportswear, Woolrich, Royal Robbins, and the area’s largest collection of Life Is Good.
St. Michaels Candy and Gifts
The secret of life’s sweetest pleasures can be found right in the heart of St. Michaels. At the St. Michaels Candy and Gifts village store, display cases are filled with handmade truffles and other world-class confectionaries. Displays of pottery, cookbooks, napkins, gourmet foods and home accents invite you to explore their unique gift opportunities.
208 Talbot serves innovative gourmet cuisine with frequently changing menus taking advantage of the area’s abundance of fresh seafood and local produce. 208 Talbot has been mentioned in Travel and Leisure, Gourmet and Mid-Atlantic Country magazines, and has been favorably reviewed by many restaurant critics. It is a local favorite.
Bistro St. Michaels
This charming re-creation of a classic French bistro is conveniently located in the heart of historic St. Michaels, Maryland. Warm atmosphere and menu prepared with local, sustainable products.
Dine outside on their deck at this very casual local gathering spot. Frozen drinks, steamed crabs and stuffed shrimp are a few of the offerings. – Their menu is sure to please.
“The only thing we overlook is the water!”
The Crab Claw
The Crab Claw Restaurant evolved from a clam shucking and crab business in the 1950s to a seafood eatery in June, 1965. Delectable fresh seafood has always been their hallmark and customers seek out the relaxed, causal setting within a stone’s throw of the water.