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Romantic and Refined - Great Oak Manor's Beauty is Unmatched

By Lena Ellwanger

Photos By Arden Haley

He may have swept you off your feet, but Great Oak Manor will carry you away with its air of elegance and romance.

The 12-room bed & breakfast was built as a residence in 1938, using Georgian architecture as its primary inspiration, making for a location that is stunning and stately, yet also charming and cozy.

Located a few minutes outside of Chestertown, the entire manor and grounds are a couple’s — and photographer’s — dream: Arrive in style up the scenic drive leading directly to the striking front entry. Stop for a photo in the garden. Pause for a pic on the porch. Inside the entrance hall, the grand, curving staircase is perfect for a dramatic entrance.

Continue on to the conservatory — added on in 2003 and a true gem in its own right. It’s an impressive space, with huge windows throughout.

“A lot of rehearsal dinners happen in here,” says Holly McKee, manager and innkeeper, “and a lot of cocktails after the ceremony, which is usually out front … Most of the outdoor weddings take place out on the grass, right on the Bay.”

Because, truly, that vantage can’t be beat. It’s the expansive views, renowned for their unmatched beauty, that make Great Oak Manor such a prized location.

The architect that built the manor, Holly says, “situated it on the banks of the Chesapeake Bay, with unparalleled views and sunsets, so it makes it extremely special here. ... It has this huge back lawn that stretches out to the Bay, which gives you lots of viewing but also great places for ceremonies.”

Fittingly, with her Southern drawl, Holly radiates charm just like the manor she is devoted to. The Georgia native has been in her role for three years. She loves Great Oak and its guests, and the fortunate few who secure the spot for their nuptials.

Holly says she enjoys getting to know the couples, “and continuing that relationship over the next year or year and a half to their wedding day. And then, when their guests come and see this place itself, they are just amazed, and that gives me a little thrill.”

She takes on only about 10 large weddings per year — ensuring there are plenty of calendar dates open for regular B&B guests while also allowing Holly to give couples her individualized attention.

“When they book for the weekend, they get exclusive use of the property for two days, from Friday to Sunday check-out. … Everybody that does that, loves it.”

Booking all the rooms allows for about 30 overnight guests. Holly says some wedding parties will stay on for additional days.

“They’re looking to have their family with them or far-flung friends from around the world. They say, ‘If they’re flying in, we don’t want them to just come for the wedding and leave,’ so they’ll book it out. ... You’re protected here, in that you’ve got so much privacy. And the serenity is what everybody talks about — about how quiet it is and the beauty of it.”

Just off the conservatory, another somewhat recent addition to the manor — the Carriage House — has also become a favored spot.

With its abundant natural light, brides and their bridesmaids love to have their hair and makeup done there, Holly says. Then, after the nuptials are complete, the newly married couple often stays in the Carriage House because it offers a spacious loft and balcony to gaze out over that coveted view.

For the reception, wedding groups will often party in a tent on the side lawn, which gives direct access to the sunporch, music room and library, common rooms that can be used for indoor cocktail space depending on the weather, Holly says.

Large weddings, which max out at 225 guests, must bring in their own caterers, serving staff and the like. Holly provides a list of recommended vendors. “The caterers that are on the list have all been here, and they’ve been very professional and responsible. And their food is delicious.”

For bigger groups coming from out of town, overflow wedding attendees can stay at the neighboring Hotel Lodge at Great Oak Landing, at other area B&Bs or at a hotel in Chestertown.

Couples be warned: Larger weddings are already being booked into 2021.

To start the process, “We request that they come here for a wedding tour,” Holly says. “I will spend anywhere from 45 minutes to two hours with them and we tour the house, I answer all their questions, we walk all over the property ... It pretty much sells itself.”

Smaller ceremonies are available Sunday to Thursday, year-round. The conservatory is popular for intimate weddings, particularly in the colder months, Holly says.

Though, not surprisingly, when Mother Nature is on their side, the couples inevitably make their way out to the lawn to tie the knot.

“That’s where they all want to be.”

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