Named one of the Top 10 Best Small Coastal Towns in America by USA Today, St. Michaels is a picturesque harbor on Maryland’s Eastern Shore. Here you’ll find the peace and tranquility you’ve been craving, along with wonderful restaurants, charming small towns, and breathtaking scenery. On our waterfront property, you’ll be able to swim in our pool, bike on our beach cruisers, kayak or paddleboard from our shoreline, or simply enjoy a glass of wine while you enjoy the view. There are tons of great things to do in St. Michaels, MD and the surrounding areas.
Kayak & Paddleboard
Paddle from The Oaks
We provide guests complimentary use of kayaks and paddleboards, so you can take to the water directly from our shoreline.
Shore Pedal and Paddle
Pair a paddling experience with a trip into St. Michaels. You can launch directly from their location at the harbor to be part of the bustling scene. Or allow them to deliver equipment to one of the other best places to kayak near St. Michaels.
Cruises & Sailing
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.
Patriot Cruises
Experience waterfront St. Michaels on the Eastern Shore of Maryland aboard the Patriot. They offer a Narrated Historic Cruise, an Island Music Cocktail Cruise, as well as private charters. Amenities include free parking, on-board bar and refreshments, indoor air conditioned spaces, a large, upper outdoor deck, and on-board bathrooms.
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)
History & Museums
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.
Historic Cruise
Enjoy a Narrated Historic Cruise with Patriot Cruises. They offer an on-board bar and refreshments, indoor air conditioned spaces, a large, upper outdoor deck, and on-board bathrooms.
Harriet Tubman Tours
Learn 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.
Frederick Douglas Tours
In Easton, you’ll find several ways to celebrate this important figure in American-American history. See the statue or mural in town or take a walking tour.
Talbot Historical Society
The Talbot Historical Society campus includes The Mary Jenkins House, The James Neall House, The Hill Research Center, and The Gardens. They house museum exhibits, collections, and scheduled events.
Biking
Bike from The Oaks
We provide guests complimentary use of bikes and helmets to tour around The Oaks. Take in the local scenery or bike down the road to grab a bite at one of the wonderful nearby restaurants.
Talbot County Trails (PDF)
Near The Oaks, you’ll find six designated biking routes that are all around 30 miles including School Days, Chesapeake Views, Joust Maryland, Talbot Farmland, Cemetery Quest, and Oxford/St. Michaels – deemed as one of the best bike trails in the Mid-Atlantic region.
Shopping
Chesapeake Bay Outfitters
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”
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.
Olivins
Premium EVOO, aged balsamic, chocolate, honey, tea and coffee. Tasting room available!
Simpatico
An independent retailer and wholesaler specializing in exclusively Made in Italy items including Italian wines & spirits, plus foods, cheeses & meats, ceramic dinnerware & accessories, kitchen linens, ornaments, Murano glass jewelry & glasses, home accessories, wall art and more. Wine tasting available!
The Christmas Shop
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.
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.
Wine, Beer & Cocktails
The Oaks Bar
We feature an on-site bar and special add-ons so you can enjoy a libation in your room or cottage, or on property.
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.
Triple Creek Winery
This winery is a true family affair. They offer a friendly environment to taste a wide variety of wines, including whites and reds. Their vineyard and winery is surrounded by farms and fields, for a relaxing vibe. They’re open to the public on weekends, but you’re welcome to make an appointment during the week as well.
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.
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 play a game of pool or listen to great live, local music!
