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Rest and Connect at Great Oak Manor

Rest and Connect at Great Oak Manor

How it started: I scrolled through Visit Kent County’s Facebook feed in search of a photo to run with this article and came across a post announcing the renovation of a Georgian-style manor into a boutique hotel.

How it ended: Driving home from Great Oak Manor after a magical 48 hours of connection and relaxation with my best friend.

Let me back up.

My best friend is moving to Texas next month. We’ve shared over ten years of living in the same state and have been there for one another through hard seasons and joyful celebrations. Knowing that soon meeting up won’t be as simple as shooting a quick text, we seized the opportunity for a just-us getaway.

Photo Credit: Great Oak Manor

We joked that we were being transported into a period film as we approached Great Oak Manor. I could practically hear stirring instrumental music playing in my ears as the house came into view. We immediately gasped and made excited girly noises. 

Corrine, one of the hotel employees, greeted us at the front desk and gave us a short tour of the property. Entering each beautifully decorated room felt like opening a present.

Photo Credit: Great Oak Manor

I swooned the most over the inviting library and immediately pulled a book off the shelf to enjoy during my stay. Our tour ended at our room (the lovely Marmaduke), where we took our time unpacking, oohing and aahing over the many thoughtful touches designed to make guests feel pampered.

Photo Credit: Great Oak Manor

We enjoyed a delicious three-course dinner in the dining room, including an entree of perfectly cooked scallops nested between fresh English peas, before climbing into a hammock on the lawn overlooking the tranquil waters of the Chesapeake Bay. Despite having spent only a couple of hours on the property, we agreed we had already enjoyed a five-star experience.

Like a child, I was too excited to sleep in the following day. I headed straight to the Chesapeake Room, a den-like space where the property’s original bar now serves as a help-yourself nook stocked with snacks, sodas, an ice machine, a fancy coffee machine, and a wine dispenser. (Guests are given a prepaid debit card with which to enjoy the dispenser!) The coffee machine served up a perfect cappuccino, which I enjoyed with biscotti in front of the massive windows in the sunroom. Watching a group of deer frolic in the early morning light only added to the feeling of experiencing something truly sensational—a feeling that never left during my stay. 

Photo Credit: Great Oak Manor

We were confident breakfast wouldn’t disappoint after experiencing Chef Mallory’s dinner, and we were right. After breakfast, we met Brooks Bradbury, the General Manager. He filled us in on some of the property’s fascinating history, gave us a tour of the Carriage House, and shared plans for hosting cooking classes and competitions, among other gatherings. I told Brooks I noticed all of the furniture in the communal spaces seemed intentionally designed for conversation and rest. My observation delighted him, and he shared part of the owners’ mission statement with us: “We have learned that people need smaller-scale, restorative environments to support and further develop their relationship needs. We believe Great Oak Manor is the perfect place for us to continue our life mission of helping people build and maintain meaningful relationships. For solo travelers, couples, family, and friend groups, we want to become a first-choice option for connection, learning, and wellness.”

Mission accomplished!

We spent the rest of our morning playing tennis in Rock Hall before driving south to Eastern Neck Wildlife Refuge for a leisurely walk. Kent County is the least populated county in Maryland, and its charming rural culture and picturesque waterfront towns offer the perfect escape for travelers seeking a peaceful place to unwind.

Photo Credit: Laurel Lagan

Knowing we had a reservation for dinner in Chestertown, we headed back to Great Oak Manor to give ourselves plenty of time to freshen up. We couldn’t resist the appeal of the private beach, though, so we threw on our bathing suits and braved the cold Chesapeake Bay just to say we did it.

I finished getting ready first and nestled into “my couch” in the sunroom with a glass of wine and a book. I found it difficult to concentrate on my book when all I could think about was how incredibly lucky I felt to be experiencing such luxury! 

Those feelings continued during our dinner at Watershed Alley. Our friendly waitress patiently answered my many questions about their menu (I had a tough time choosing because everything sounded fantastic). Our dishes and drinks were phenomenal, but we were especially impressed by the decadent lobster tortellini (made in-house) and a truly memorable side dish of baby heirloom carrots with a curry yogurt sauce and gingerbread soil.

If you ever stay at Great Oak Manor, and I hope you will, you absolutely must be on the property to view the sunset over the Bay. We sat in the Adirondack chairs perfectly placed for prime sunset-watching and played a card game in between taking pictures of the changing sky. 

Photo Credit: Great Oak Manor

“I don’t want to leave,” Laurel said, and her words hung in the air as we thought about the imminent end of our girls’ getaway and, in mere weeks, the end of living within driving distance of one another. 

“Let’s not talk about it,” I begged, knowing a wave of sadness could easily surface, and we quickly went back to chatting about the special memories we’d made in such a short time.

Even with other guests sharing the property, there are plenty of places to go if you seek a private place to read or talk. I spent part of my Saturday morning the same way I spent the morning before—sipping a cappuccino in the sunroom—before heading to the library to write in my journal. Laurel came down a bit later, and we enjoyed another superb breakfast. 

Photo Credit: Laurel Lagan

While it was tempting to head to Chestertown to check out their annual Tea Party Festival, we wanted to spend as much time as possible enjoying our luxurious accommodations. We lazed in the hammock, played several rounds of cornhole, and took advantage of the hotel’s bikes to go for a slow, scenic ride. We planned to leave after our bike ride but couldn’t resist playing one more round of cornhole before reluctantly hitting the road. 

One of the aspects of our stay that made it so memorable was the absence of rush; we savored each moment at our own pace. I don’t have any regrets about spending most of our time at the Manor, but if I could do it all over again (and I plan to), I’d build in time to explore more of Chestertown.

As I look through photos of our trip, I see two women fully relaxed and happy to be in one another’s company. Laurel’s presence in my life is one of my life’s greatest gifts, and our time at Great Oak Manor was a cherished chapter in the story of our friendship.


Feature Photo Credit: Great Oak Manor

About the Author

Laura Rennie is the Editorial Manager of Maryland Road Trips and also works as a freelance writer. She loves a good burger and often plans her travels around food. Laura lives in Myersville, MD, with her husband and daughter. She can be reached at

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