The Chesapeake is always beautiful, but the small towns and waterways are particularly charming over the holiday season. Check out my 2024 Holiday Guide to the Eastern Shore’s best holiday festivals, activities, dining, parades, and more!

Selecting a place for its peaceful vistas, small towns and sunsets across open water first—and building second—provides maximum home customization in an unforgettable, perfect-for-you location. But buying land in this rural, river-oriented environment presents unique opportunities as well as some challenges. If you’re considering purchasing a slice of Maryland’s scenic landscapes or waterways, keep these essential tips in mind to make your experience positive and successful.

House hunting in-person can be stressful for many buyers, but searching for a new home remotely can be overwhelming—especially when so many aspects of Eastern Shore life don’t translate to a search engine! If you’re looking for your Chesapeake home, here’s a few suggestions to make the process as smooth as possible.

Buying a home in the Chesapeake is not just a transaction— whether you're drawn to the historic waterfront towns or the tranquil rural landscapes, it's crucial keep your priorities in mind as you navigate the real estate process with care and attention to detail.

Here are my recommended interior and exterior home improvement projects for 2024, tailored to the Shore’s specific needs and market trends—and what you can expect to recoup on your investment.

Selling can look daunting from the outset, but there are some simple strategies you can use to put your best foot forward as you consider listing your home. Born and raised in the “Pearl of the Chesapeake,” Rock Hall, Maryland, I thought I’d share a few selling “pearls” of my own to to ensure you have a smooth experience.

Though the Chesapeake’s winters are usually mild, some snow and ice is to be expected. Use my checklist to help you batten down the hatches as you prepare for the cold, beautiful months on the Eastern Shore.

We can learn some lessons about life’s changes, the turns of the season, and simplifying from our feathered friends. For many of us, our fledglings are now grown. Or our nests, once cozy, were built for a life that has transformed. If we’re not flying south this winter, it’s time to think about what nest is right for us, right now.

Nothing quite captures the life and vibrance of the Chesapeake summer spirit quite like the annual re-opening of the dock bars. These waterfront watering holes are cruising destinations and entertainment venues, luring patrons by water and land with live music, food, and sunny decks all summer long. Each Eastern Shore waterfront community has their own dock bar, but we wanted to share a few of our must-visit favorites in Talbot, Queen Anne’s and Kent Counties.

It’s late spring on the Eastern Shore and that means it’s time to get that yard and landscaping looking beautiful. But the work you put into your property’s lawn and plantings can make all the difference when it comes to selling your home. Read our pro tips for some easy ways to refresh your property and turn the heads of your home’s potential buyers.

Throughout the year, the communities of the Eastern Shore create different ways to celebrate the season. Distinctive to each county’s landscape and traditions, these festivals and events annually enliven life in Talbot, Queen Anne’s and Kent County.

Winter is a good time for fulfilling that resolution to make this place your home. Maybe you’ve been coming to the Eastern Shore since you were a kid. Maybe you love boating here and have always dreamed about dropping anchor here for good. You know who you are—you are a future Eastern Shore resident. So why wait?

From a gentle rise overlooking a quiet tributary of Langford Creek, the main house of Wings & Whitetail Farm surveys the landscape as it has for 265 years. Once called “Bungay Hill,” this 18th century home in Kent County, Maryland is one of the county’s most important historic properties. Currently available for purchase, it is a rare opportunity to own one of the finest country estates on the Eastern Shore.

In Rock Hall, the Old Oars Inn Bar and Restaurant on Main Street was a beloved third space. A watering hole par excellence, you could chat with a waterman over a $.75 Budweiser and a burger, meet a friend for dinner, or just nurse a drink and wind down your day. As a meeting place, it worked out well because it was hard to miss—the proud bow of a Chesapeake Bay deadrise had been prominently fixed to the right side of the building.

But just like holding out for those teeming river crabs of high summer, folks who have waited until now to buy their home are benefiting from a renewed supply and shifting market.

Every spring, there’s a lot of competition in the osprey world for the ideal nesting site, and aerial battles are common as osprey duke it out for the best tree, dock piling or telephone pole. It’s spring fever, Eastern Shore-style, and seems like a familiar scenario to anyone in the current real estate market.

“Home should be an anchor, a port in a storm, a refuge, a happy place in which to dwell, a place where we can love and be loved.”  -Marvin Ashton

Our peace on earth is here, on the Eastern Shore.  As I decorate for Christmas this year, celebrating one year in our new home, I am grateful for taking this risk and celebrating the life we have recreated for ourselves in this beautiful place. 

There’s no other way to say it—2020 and the first part of 2021 have been a wild ride. The incredible pandemic-fueled real estate boom has created a truly unprecedented seller’s market, especially for buyers looking for a piece of the Eastern Shore good life.

From the water or from the land, the first impression of North Point Marina is the same— welcoming, immaculate, and well-equipped. Located in the protected waters of Rock Hall Harbor, North Point Marina has commanding, 180 degrees vistas of the open Chesapeake.

Every year, as the leaves start to shade into browns and golds, they start to show up. At first, a trickle, and then in droves, their growing numbers make it clear the word is out—the Eastern Shore’s sheltered waterways and quiet fields are a beacon of safety and calm.