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Maryland Eastern Shore Living

1001 Reasons to Love Maryland’s Eastern Shore

If you want sports arenas, boutique hotels, and trendy food courts, head to Baltimore. But if it’s antiques, small towns, or the beauty of an indrawn tide you’re after, Maryland’s eastern shore is your spot. You won’t need your designer clothes here – in a landscape that stretches for acres where all you see is marshes.

Yet with the northern corners of Cecil County perched conveniently halfway between the Philadelphia and Baltimore airports, the Eastern Shore is never too far away from the necessities of modern life… like international travel, big-city culture, or an Orioles game. Should you feel the urge to visit our nation’s capital, it’s a two-hour drive to downtown DC.

Proximity to big metro regions like DC/Baltimore/Wilmington/Philadelphia is only one aspect of the region that people love. Here are a few of the other thousand reasons to love Maryland’s Eastern Shore.

The Upper Portions are Spectacular

As the Susquehanna River makes its way from Upstate New York, through Pennsylvania, it finally empties into the upper regions of the Chesapeake waterway system. That’s where you’ll find some of the best spots of the Eastern Shore, including beautiful Cecil County. This county forms the northern boundaries of what folks down here call the Eastern Shore – go any further north you’re practically inland, as far as locals are concerned.

Follow your nose southward through Cecil County and you’ll find yourself in Kent County, followed by Queen Anne’s County. All of the eastern shore is lovely but each county has its unique specialties that endear the micro-regions to those who are lucky enough to live there.

Among the many reasons residents love it here is the rich history that permeates the region.

Beyond Beaches: There’s a Rich History Here, Too


Historic downtown Chestertown is home to The Bordley History Center, an impressive spot for history buffs, complete with museum, a research library, and a fabulous genealogical space for locals to learn about their heritage. For those who don’t get the chance to visit the excellent genealogical facilities, online resources such as Genealogy Bank are also very useful when it comes to looking at family lineage. Locals who every so often feel a yearning to learn something new can attend History Happy Hours on the first Friday of every month. The center hosts history lectures, seminars, and discussions… all with wine served!
There’s a good reason that Kent County Historical Society chose Chestertown for its annual Historic House Tour. The National Landmark Historic District has more 1700s-era homes than any other town in the state, outside Annapolis.

There’s even St. Paul’s Episcopal Church, whose cemetery hosts graves from the 1600s.

And if Chesapeake Bay history is your passion, Chestertown is home to the Sultana Education Foundation and the Schooner Sultana. The schooner is known to be one of the most historically accurate replicas of an 18th-century schooner in the world.

North East

At the head of the North East River, in the northeast corner of Maryland, lies the appropriately-named town of North East. With just around 3,600 residents, it’s hard to believe this tiny town experienced a population explosion between 2000 and 2010 but it did. Gaining almost a third of its population again in just that decade, it witnessed nearly 43 percent population growth after a significant decline in the 1970s. Growth has slowed down since 2010 and luckily, North East retains its small-town charm. Home to a 1700s-era church (St. Mary Anne’s Episcopal Church) and the Turkey Point Light Station, North East is a cultural and historical place of interest.

Rock Hall

If you ever need to clear your mind and travel back to a time when things moved at a quieter pace and folks didn’t seem to worry about much more than incoming storms, you might want to visit Rock Hall. There are over a dozen marinas here, plus the Eastern Neck National Wildlife Refuge. Find nesting Bald Eagles and over 230 species of birds in the refuge, enough to keep even the most casual birding enthusiast occupied for a lifetime.

But this is about the historical significance of these gorgeous spots, and Rock Hall has that too. A stroll through Wesley Chapel reveals endless historic headstones, as do the cemeteries at St. John’s Catholic Church and Asbury United Methodist Church.

An Overlooked Historical Figure from the Eastern Shore Every School Kid Should Know About…

The Eastern Shore of Maryland has spawned more than a few historical figures, as well. A little-known fact is that Abraham Lincoln had a female cabinet member: Anne Ella Carroll. Fulfilling the difficult role of advisor to Lincoln’s cabinet during the Civil War, Ms. Carroll also published an endless stream of pamphlets where she railed against slavery. Born on the Eastern Shore of Maryland (in Pocomoke City), she represents one of America’s most overlooked female heroines and you can visit her grave in Church Creek, further down the Eastern Shore in Dorchester County.

Cultural Roots Run Deep on the Eastern Shore

And speaking of the Civil War, people in Maryland consider themselves to be Northerners, even though the state is located South of the Mason-Dixon Line. The Eastern Shore, on the other hand, is considered Southern territory, through and through. If you ask locals why, they’ll respond that they feel that Southern culture is more in line with their own way of life and for that reason they hold true to that old Mason Dixon line!

And to go along with that Southern Price, Eastern Shore folks also have a stronger sense of “County Pride”. It’s a Maryland thing, actually. The County Fair is still a very big deal and you’ll see bumper stickers proclaiming county pride as you navigate the roads that thread through the area. With that in mind, here are some counties on the Eastern Shore that you’d be especially proud to call home.

Cecil County

Coastal Living Magazine named Cecil County’s Chesapeake City one of the top ten best small towns on the Chesapeake Bay. Need we say more?

Kent County

One of the biggest draws of Kent County is the historical society there, which is known to be extremely active. We’ve already mentioned Chestertown, which is in Kent County. There’s also the Massey Air Museum, with vintage airplanes and the chance to watch ongoing restoration projects.
The town of Rock Hall is also in Kent County and home to the Rock Hall Marine Restoration and Heritage Center. Water trails abound here, including the fascinating Captain John Smith Chesapeake National Historic Water Trail. During your paddling excursions, you can imagine the famous captain and his crew as they journeyed up the Chesapeake Bay in search of the Northwest Passage. The Chesapeake wasn’t it, of course, but the group did manage to map almost 3,000 miles of the territory.

Queen Anne’s County

With 265 miles of waterfront, including Kent Island, Queen Anne’s County is a national treasure. Kent Island is the largest island in the entire Chesapeake Bay, not to mention an important historical spot. Native Americans lived here for 12,000 years before the British arrived in 1631 to form the first settlement in the state.

Nature Lovers Will Think They’re in Heaven

If your idea of the perfect commute is rolling by endless fields under endless skies, you’ll love living and working on the Eastern Shore. Catch glimpses of Bald Eagles, spot Great Blue Herons as you cross rivers, and even the occasional falcon searching for a meal on the riverbanks. Enjoy mile after miles of undeveloped terrain, untouched by development, as you make your way to work, shopping, or wherever your local errands take you in town.

Fields, rivers, marshes, and the waterfowl that thrive in and around them all await those who venture eastward across the Chesapeake Bay Bridge

Sports are Also a Big Thing

As if an incredible natural environment and a rich history weren’t enough, there’s a lot more going on here, too. It’s not all just fishing, birding, and hiking.

While they have to drive quite a ways to catch an Orioles game over in Baltimore, Eastern Shorers are no stranger to sports. For a region that only eight percent of Marylanders call home, the Eastern Shore has a large number of sports figures who have hailed from the region. All you have to do is look at “sports-famous” (and semi-famous) graduates of the Eastern Shore branch of the University of Maryland to get an idea of how important sports are to the region. These include Art Shell, Football Hall of Famer and Charlie Mays, Olympic Athlete as well as countless NFL and AFL players and coaches.

There’s a Touch of Academics So Your Brain Won’t Starve

Kudos to UMES, which was recently recognized as having Maryland’s highest first-time pass rate on the pharmacy board exam. A historically black college, UMES has graduated many famous and important actors, musicians, athletes, writers, politicians, scientists, researchers, and leaders over the years.
In Chestertown, we have Washington College, the nation’s tenth-oldest college.
Bottom line: it’s nice to know that, even if you choose to live in a remote area, there’s still a flourishing center of intellectual stimulation and cultural events nearby!

A Few Tax-Related Reasons to Love the Eastern Shore…

Even the tax situation gives us a few more reasons to love the Eastern Shore.

Real Estate Taxes

Overall, the State of Maryland ranks in the 31st position out of fifty states and Washington, DC in terms of property taxes in 2019. There are thirty states with lower property taxes but you could do worse – in twenty other states, including Rhode Island, which has an effective real-estate tax rate of 1.66%, compared to Maryland’s 1.10%. And New Jersey, at the highest position at #51, has an effective rate of 2.44%, more than double that of Maryland’s!

Plus, while other states have shifted their real estate tax rates over time, Maryland’s has been consistent, which points to a certain financial stability. Knowing your tax rates are less likely to shoot upwards any time in the near future counts for a lot when you’re relocating for retirement (or any other reason, for that matter).

Business Taxes

As far as business taxes go, Maryland fares quite well in structuring their tax system to serve as a blueprint for economic improvement. While it didn’t make the Top Ten best States for business taxes, it wasn’t on the Top Ten Worst States, either, according to the Tax Foundation.

The 2019 State Business Tax Climate Index places the State of Maryland squarely outside either end of the spectrum with an overall rank of 40 and in impressively low sales tax rank of 18 out of 51 (50 states and Washington, DC). Again, stability is the key in the state, as their business taxes changed nary a decimal point between 2016 and 2019, according to the Tax Foundation.

Within the state, Queen Anne’s County, Cecil County, and Kent County, covering the Eastern Shore of Maryland, fall well below tax rates of Howard County, Frederick County, and several others in terms of property taxes.

Point being… you could do much worse, tax-wise, in relocating to Maryland’s Eastern Shore.

Retiree Taxes

Seniors and retirees, on the other hand, fare quite well in Maryland and the Eastern Shore. Maryland does not tax Social Security benefits. In addition, folks who are 65 or older and who receive taxable pension and retirement annuity income may be able to subtract some of that income on the Maryland state taxes. This also applies to you if you are totally disabled. This is called the standard pension exclusion.

The state also grants tax benefits to certain retired individuals who are not eligible for the standard pension exclusion. There is a $15,000 pension exclusion on state taxes if you are a retired…

  • Police officer
  • Emergency services personnel
  • Correctional officer
  • Fire, rescue personnel
  • Other law enforcement personnel.

There are qualifications to meet, which are listed on the Comptroller of Maryland’s website.

Other retiree-related tax benefits of moving to Maryland’s Eastern Shore include the following.

  • A tax break for long-term care insurance: one-time credit up to $500
  • An additional personal exemption on state taxes for seniors
  • Married seniors who both receive income may subtract up to $1,200
  • Military retirees and spouses who receive military retirement income also get a tax break of up to $5,000 and if you are 65 or older, that amount jumps up to $10,000
  • Federal worker retirees can have Maryland taxes withheld from their federal pension

Keep in mind that each tax break or benefit comes with terms that you’ll have to meet in order to qualify.

There’s More to Maryland’s Eastern Shore Than Meets the Eye

As comprehensive as this guide seems, it still doesn’t come close to capturing the true essence of the Eastern Shore. From the deep historical roots to the incredibly beautiful nature preserves and quaint towns full of Southern charm, the region will forever be yielding up its own unique blend of pleasures and delights. Whether you move here from nearby or you’re a transplant from fields afar, you’re going to love discovering the remaining 900 or so reasons to love Maryland’s Eastern Shore.

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  • Michael Kelczewski

    5701 Kennett Pike Wilmington, Delaware, 19807



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