About St. Michaels

St. Michaels Maryland


Come visit St. Michaels, a picturesque harbor on Maryland’s Eastern Shore. St. Michael’s was named 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]


Swim in our pool, bicycle on our beach cruisers, putt on our greens, and enjoy crabbing and fishing off of our private dock. Experience the beautiful sunset while canoeing in peaceful Oak Creek, an inlet of the Miles River. Enjoy a game of shuffleboard, badminton, horseshoes, or volleyball.


Or, simply enjoy a glass of wine waterside in one of our Adirondack chairs. Great Blue Herons, Ospreys, and transient Canada Geese are frequently spotted from our shoreline. Occasionally, we experience a Bald Eagle sighting!

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.

Lady Patty Classic Yacht Charters
Lady Patty is a beautiful 45′ offshore race boat built in 1935. Join us to experience the elegance of classic yacht sailing surrounded by honey-varnished teak and polished bronze under towering wind-filled sails on the beautiful Chesapeake Bay!

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.

Ophiuroidea “The O” is located in the Town of St. Michaels, Maryland and the
Kent Narrows in Grasonville close to marinas, hotels and restaurants.
Coastal inspired boutique offering clothing, unique and handcrafted coastal items, mermaid art, sea glass jewelry, coastal furniture & home decor and one of a kind finds.

Premium EVOO, Aged Balsamic, Chocolate, Honey, Tea and Coffee. Tasting room.

Simpatico is an independent retailer and wholesaler specializing in exclusively Made in Italy items: a fabulous selection of Italian wines & spirits, plus foods, cheeses & meats, ceramic dinnerware & accessories, kitchen linens, ornaments, Murano glass jewelry & glasses, home accessories, wall art and more. Wine tastings available!

The Christmas Shop
The Christmas Shop in St. Michaels is a Christmas Shop for All Seasons. They offer the charms of the Eastern Shore and specially selected gifts from around the world.

DBS Jewelers
Stop in to see their Unique Collection of Designer Jewelry featuring One-of-a-kind Creations set in Gold or Platinum, with Precious Gemstones. The Fine Jewelers of St. Michaels.

Come By Chance
A coastal inspired lifestyle store. Catering to the casual sophisticate, offering unique gifts, one of a kind pieces and complete design services for your home.


208 Talbot
208 Talbot serves innovative gourmet cuisine with frequently changing menus taking advantage of the area’s abundance of fresh seafood and local produce. They have also 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.

St. Michaels Crab and Steak House

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.

Ava’s Pizzeria and Wine Bar
Brick oven pizzas, fresh salads and more in the heart of St. Michaels. 410 745 3081

Local Activities

Skipjack Cruise

Experience the Chesapeake Bay onboard the national historic landmark the Rebecca T. Ruark. Hoist the sails, steer to an oyster bar and dredge for oysters as you learn about the bay from a 3rd generation skipjack waterman – the infamous Captain Wade!

(Seasonal Availability)

Harriet Tubman Tours | 1.866.642.7743

Harriet Tubman Tours provides insights about the life and legacy of Harriet Tubman and surrounding History. All of their guides completed the same training given to rangers of the Harriet Tubman National Monument and State Park. In addition to knowing Harriet’s story, they are well-versed in the history and lore of the region.

Patriot Narrated Historical Cruises

Experience waterfront St. Michaels on the Eastern Shore of Maryland aboard the Patriot. The 65-75 minute scenic river cruise is a delightful experience for all ages.  Amenities include free parking, on-board bar and refreshments, indoor air conditioned spaces, a large, upper outdoor deck, and on-board bathrooms.