A Charming Stay at Kent Island Resort

I must admit I’m one of tens of millions of road-trippers who whoosh along the Chesapeake Bay Bridge each year, crossing Kent Island faster than a D.C. city minute en route to shore-based relaxation and adventure.

Once I found out that Kent Island is the gateway to Maryland’s Eastern Shore and way more than a pit stop, my husband Derek and I knew we had to make an overnight trip happen. And I knew we had to anchor our stay at Kent Island Resort, where charm, sophistication, and relaxation seamlessly connect.


Inviting Location

The boutique country inn sits on 220 acres of pristine farmland located just outside Stevensville and mere minutes from the Bay Bridge. We knew we were in for a treat as we entered the estate along a curving tree-lined drive and spied the restored 1820s manor house from a distance.

Exterior of giant resort building on Kent Island
Photo Credit: Kent Island Resort

As perhaps they did 200 years ago, the staff welcomed us with attentive hospitality and fresh squeezed lemonade. The clean, luxe room welcomed us with a comfy bed and romantic views. Our two nights of sleep were so restful. Thanks to the resort’s tucked-away location, the only sounds we heard were the birds in the morning!

Pro tip: Look for the secret staircase leading up to the cupola on the top floor of the main house. It’s tradition for visitors to inscribe their names on the walls—bring a marker so you can do the same. Stay awhile for the 360-degree views!

Concerts & Events

Don’t worry—this quiet property knows how to turn up the energy when the moment calls for it! On select summertime evenings, the resort hosts its Rock Kent Summer outdoor concert series. 

People enjoying an outdoor concert by the water
Photo Credit: Chelsea McCallister

We joined guests and locals who came out to boogie on the lawn to the live sounds of disco. Everyone had a smile on their face! Whether you plan to stay at Kent Island Resort or come for a meal, be sure to check out the events calendar for concert tickets as well as upcoming barre and yoga classes, fireside s’mores nights, wine tastings, themed dinners, walking tours, and stargazing meetups.  

Recreation & Relaxation

Explore the resort’s nearly 2 miles of waterfront from the water. Head to the boat house to rent a kayak or stand up paddleboard. I loved my time paddling on the gentle creek. You can even hop on a jet ski—the resort just acquired a pair. The resort also has a great swimming pool, meandering walking trails, games like bocce and horseshoes, and bikes to rent!

Photo Credit: Kent Island Resort

Nearly every corner of the property offers a serene place to sit and relax. The hammocks under the shady grove of trees are a good spot to read (and take a cat nap, like I did). Derek and I also loved spending cool evenings lounging in a cabana or on reclining chairs at the private creek-side beach.

Sip & Savor 

Kent Island Resort has two dining options to fit most budgets, with menus designed by an expert chef. For an intimate dining experience, we enjoyed locally sourced seafood, satisfying cocktails, and a very popular brunch at 18TWENTY Bar & Restaurant. Over at The Beach Bar, we savored a crab cake sandwich, chicken nachos, and ice-cold beer. 

Nachos in a cone
Photo Credit: Chelsea McCallister

Derek and I thoroughly enjoyed both dining options. On one day of our stay, we had a crab omelet for brunch and crab dip in the evening. I say that a day bookended by crab is a very good Maryland day!

Terrapins Live Here!

The resort has an unexpected ecological bonus: real terps! A mama terrapin discovered the man-made sandy beach and buried her eggs there. The resort staff have cordoned off the terrapin nest with cones and signage and are keeping vigil over it.

Sign on the beach alerting guests of turtle nesting
Photo Credit: Chelsea McCallister

Perhaps the turtles came not only for the beach but also for the live music!

Derek and I loved easing into quiet shore life during our stay at Kent Island Resort. We can’t wait to return with our boy Oliver. We know he will love the omelets, water sports, lawn games, and the terrapin nest!

More to Explore


This article is sponsored by Kent Island Resort. Less than an hour from Washington D.C., Kent Island Resort is a sophisticated countryside retreat where guests enjoy the best farm and river-to-table cuisine and curated experiences. Learn more and book your stay at kentislandresort.com.

Feature Photo courtesy of Kent Island Resort

About the Author

A native of Las Vegas, NV, Chelsea Milko McAllister resides in the historic Baltimore neighborhood of Charles Village with her new husband and stepson. Her foreign policy career and travel obsession have taken her to over 50 countries, including Uganda, where she served as a U.S. Peace Corps Volunteer. Chelsea loves documenting her Maryland adventures through writing and photography. Follow her on Instagram @themilkoway.

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