Easton, Maryland
Easton, Maryland

Top 5 Summer Activities in St. Michaels, MD

Here at The Oaks, we understand the importance of getting away, of taking a well-deserved break from the hustle and bustle of daily life. We are uniquely poised to offer a luxurious property perfect for both midweek stays and as the ideal destination for an unforgettable wedding! Whether you’re the bride and groom looking for excellent accommodations for their wedding party or simply seeking a relaxing getaway, you can rest assured knowing The Oaks has everything you need to make it happen. We have a wide variety of summer activities in St. Michaels, MD, with plenty for you or your wedding party to do in this beautiful area of Maryland.

couple on a getaway together in St. Michaels

Aquatic Activities

We offer complimentary kayak and paddleboard rentals for water-based excursions—a great way to enjoy the outdoors and explore the waterways. Another great way to see the sights is on a Patriot Cruise. Learn more about Maryland’s rich colonial history on one of their narrated tours, kick back and relax on the Island Music Cocktail Cruise, or book a private charter for the whole group and have an exciting day out on the water. Take a relaxing sailboat tour on the Selina II and take it all in with a classic sailing experience, or watch fishers bring in their catch at ports around the area, a true New England hallmark.

on a classic wooden sailing ship in Maryland

Historical Exploration

While you’re here in St. Michaels, we highly recommend a visit to the Chesapeake Bay Maritime Museum, a must-see that documents the area’s long maritime history. Learn more about Maryland’s role in America’s early history and its path to becoming an economic powerhouse and trade hub. The museum also holds events like special exhibitions, festivals, outdoor summer concerts, and even boatbuilding classes! It’s one of the best ways to connect with local culture as well as dive into the fascinating stories of the men and women who lived here for hundreds of years. You can see some of the locations mentioned in James Michener’s landmark novel “Chesapeake” and dive into the area’s significant ties to abolition and significant individuals like Frederich Douglas and Harriet Tubman.

Bikes in front of Cottages in Maryland Eastern Shore

Biking Adventures

Embark on a cycling journey at The Oaks with our complimentary bikes and helmets available to our guests. We have dedicated trails around the hotel for exploring the town and surrounding area, ideal for a summer day spent seeing the sights! In particular, the Oxford/St. Michaels Trail is easily one of the best in the Mid-Atlantic region, with stunning views of nature and well-maintained trails for a safe and fun cycling experience. Whether it’s just the two of you or the whole wedding party, everyone is sure to love a breezy day in the great outdoors with so many sights to see.

couple shopping together enjoying one of the best activities in St. Michaels, MD

Shopping Excursions

Stock up at Chesapeake Traders and grab delicious foodstuffs for a summer picnic, late-night deserts, or cooking your own meals in one of our private cottages. There are plenty of other shops nearby as well for wedding gifts, handcrafted goods, and so much more. Make a day of it and explore to your heart’s content, with plenty of shopping to be had both in and around St. Michaels. End an exciting day with dinner at Bistro St. Michaels, a cozy eatery serving up the best in New England cuisine, fresh seafood, and refreshing cocktails.

Bar and dining room at Chesapeake Bay bed and breakfast

Wine Tasting Experiences

Taste the best that St. Michaels has to offer with a wine-tasting adventure at St. Michaels Winery or Triple Creek Winery. Your guests will love the opportunity to sample delicious Maryland wines and enjoy gorgeous views of the countryside. St. Michaels Winery offers the option to book a private tour of their winemaking space, an ideal activity with plenty of room for an afternoon wedding party. The atmosphere of Triple Creek Winery is simply unmatched, a rural location surrounded by farms and fields for an out-of-the-way excursion with a relaxed vibe. You don’t have to go out of your way for a fantastic glass of wine at The Oaks, or our cozy hotel bar, the perfect place to talk with guests and socialize over a craft beer or mixed drink. In addition, stop by Eastern Shore Brewing for a refreshing pint of local craft beer and award-winning libations in a cozy taproom.

King bed and living area in spacious Junior Suite 29 at The Oaks


Premier Lodging

Book your relaxing getaway or destination wedding at The Oaks for an unmatched experience in an exclusive setting. Our fully renovated waterfront estate provides everything you need for a comfortable stay in St. Michaels. Our luxurious accommodations feature three options to choose from: the deluxe rooms in the main building, suites for more space, or private cottages with more amenities for groups, like kitchens, extra living space, and more. All include king and queen beds fitted with high-quality sheets, stunning views of the water from your room or private balcony, and many feature walk-in showers and soaking tubs for soothing relaxation. Your wedding party is sure to love our gorgeous property and convenient location, with plenty of activities for everyone! Whether it’s the whole group or just the two of you, we have everything you need to ensure a memorable and incredible Maryland stay.

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Water inlet at waterfront wedding venue and hotel in Maryland