A waterfront wonder: The Oaks is a ‘blank canvas’ for couples

Story by Elizabeth Polo

Photos submitted by The Oaks

Nestled along the serene shores of the Chesapeake Bay, The Oaks Waterfront Hotel is an intimate wedding venue offering an escape to the charming Eastern Shore of Maryland. The quiet atmosphere in St. Michaels gives couples the dream waterfront wedding experience. Imagine professing your vows as the sounds of waves lap the shore, leaves rustling in the wind. Whether grand or small-scale celebrations, The Oaks paints the perfect picture of natural beauty and love.

Resting on 10 acres of land, The Oaks offers a wide variety of locations to tie the knot. From the grand lawn overlooking the water to a spacious waterfront ballroom and even an enclosed dock, the property can fit any size wedding to make your dreams come true.

The biggest spaces on the property are the grand lawn, which can hold about 350 guests, and the waterfront ballroom, which can hold around 200. The dock, which can accommodate around 80 people, is perfect for smaller weddings.

A central value The Oaks maintains for its guests is ensuring the space is exclusively yours on your big day, providing an intimate, undivided destination. This means having the entire property to yourself. Ashton Yates, the hotel’s wedding venue and banquet manager, shared that this touch ensures that this is your home for the weekend.

“With most wedding venues today, there could be one or more than one wedding going on at the same time as your wedding, and it does make a big difference because of how the staff interacts with all these weddings,” she said. “So, here, just being the only wedding that weekend, you don’t have to worry about random people coming in.”

During your weekend stay, you and your guests can enjoy complimentary breakfast and outdoor activities such as paddle boarding, kayaking, biking, canoeing and a chartered Hinckley Yacht. 

According to The Oaks, the property was historically included in a land grant given by Lord Baltimore to the Benson family around 1680. Over the centuries, the property evolved to house guests. In 1884, the land was made into a farm, and in 1902, the owners built a boarding house for people traveling to the area by steamboat or railroad. In the 70s, The Oaks was purchased to be transformed into a hotel resort, and in 2022, Scott and Tracy Wagner added their magical touches to turn The Oaks into the beautiful getaway it is today.

“The owners, Scott and Tracy, are wonderful people,” Yates said. “They are really involved in the community, and they take a lot of pride and joy in keeping this place going. A lot of the parents of these couples have even mentioned that they can tell it’s a family-owned business.”

With the emphasis on “family,” The Oaks make sure every single couple is guaranteed free-reign to make the place their own.

“It’s really a blank canvas,” Yates chuckled. “A lot of couples want to have their personality or something that excites them added to the property. No two weddings are ever going to be the same here.”

In preparation for the ceremony, The Oaks offers both a bridal cottage, which includes a luxury kitchen and bathroom, a waterfront view, a vanity, a king bedroom, and a porch and a groom’s suite with a wet bar, a waterfront view, two decks and a luxury bathroom. 

For the standard rental fee, The Oaks provides ceremonial chairs, electricity, lounge furniture, and bars for cocktail hour, as well as all tables, chairs, linens, and tableware for the reception. A wedding at The Oaks also includes a full kitchen, staff, servers and bartenders. Thus, no sourcing from temp agencies is required.

The Oaks has 11 hotel rooms and four cottages. Tours are available throughout the property upon request.

The hotel can also be used for various private events, such as work parties, birthdays, or even a simple getaway. St. Michaels offers many activities outside the hotel, including sailing, museums, shopping and dining at restaurants.