Though the street signs at the centers of U.S. towns may not all read
Main, the moniker evokes a collective
impression in American society—a certain nostalgia that harkens back to a
simpler life, a sense of belonging, a safe place to go.
Bucolic Kent County, Maryland’s smallest, delivers this sensibility on
nearly every street you travel. Perhaps it’s due to geography. Practically an
island, with roughly 93% of its borders defined by the Chesapeake Bay and the
Sassafras and Chester rivers, the county is naturally preserved from the hustle
of nearby Baltimore, Washington and Philadelphia. Or, might it be in the air?
Breathe the salty spray along the bay, the earthy aroma of winding rivers or
the pastoral perfume of nearby fruit and vegetable farms, and your body
immediately downshifts to a pace that befits a Main Street stroll.
In 1998, the Maryland Department of Housing and Community
Development created the Main
Street Maryland Program with a vision to restore and revitalize historic, culturally
significant, downtown districts by providing funding for planning, marketing
and education. Through a competitive process, 26 communities have currently
received this official designation. Chestertown is one of those communities, and they worked hard for
it.
A Royal Port of Entry
To earn this coveted designation, Chestertown’s residents, business owners and local government
organized to satisfy crucial requirements of the selection criteria like restoring
buildings and designing new construction to complement the historic, colonial
architecture of what was once a Royal Port of Entry; developing business and
marketing plans to create a sustainable economic engine to fuel growth and
future enhancements; instilling a sense of pride throughout the entire city to
create and maintain a safe, clean and green community.
Evidence of their high standards can be found around every corner.
From the town landing, where visitors first stepped into the municipality some
300 years ago, stately homes stand proud—like Widehall, a Georgian-style
mansion built by Thomas Smyth in 1769 and later home to a Maryland governor and
state senator, or the blue-shuttered Watkins house, believed to be the oldest
surviving home (circa 1739) on Water Street. This area along the waterfront and
its adjacent streets were designated a National Historic Landmark in 1970 and Widehall
was listed on the National Register of Historic Places in 1972 (Chestertown
claims another 20 of the 41 sites in the county).
Continuing along
the brick-paved sidewalks of High Street, you’ll parade past many more quaint
homes in the Chestertown Historic District and into the heart of downtown (a
state designated Arts and Entertainment District) where a variety of shops and restaurants add charm and character. Browse art galleries and
studios, furniture and antique stores, new and resale boutiques, jewelers,
bookstores, gifts and novelty shops, bakeries and natural food shops.
Take it all in
and stay for a while. Choose
from distinctive bed and breakfasts in storied manors to branded hotels
throughout Chestertown and beyond.
A Presidential Promenade
During Colonial times, the shortest route between Virginia and
points northward was by ferry across the Chesapeake Bay from Annapolis to Rock
Hall on the western
shore of Kent County. From there, travelers (including George Washington,
Thomas Jefferson, James Madison, and other founding fathers) frequently traversed
its main street, part of the county’s first road cut in 1675. Though presidents
and dignitaries no longer frequent its promenades, this small, seaside village
still bustles with weekend visitors who appreciate slowing their pace and
stepping back in time.
Such illustrious history warranted an associate Maryland Main
Street designation where Rock Hall Avenue and Main Street meet and where
today’s visitors enjoy enduring pastimes, locally owned restaurants and one-of-a-kind shops—like Durding’s
Store with their
old-fashioned soda counter; vintage resale and antique stores like Fishbone’s
Antiques, a pickers haven;
Bay
Wolf Restaurant serving local seafood
and Austrian specialties in a rustic tavern setting; Village
Quilting where you can get
a handmade throw to warm your bones on a chilly New England evening or Smilin’
Jake’s Casual Apparel for suitable attire on a balmy summer day.
A Place That Made a Splash
On the northern shores of Kent County where the Sassafrass River
spills into the Chesapeake Bay, another Main Street lined with Victorian homes
and antique street lamps leads through Betterton straight to their prized possession—Betterton
Beach, where you can
swim all summer long without fear of sea nettles.
And that’s just what city dwellers did during its heyday in the
roaring ‘20s. Then, steamships delivered loads of vacationers to this summer
retreat where large hotels, taverns and dance halls lined the bluffs and grassy
knolls overlooking the waterway. Today, those establishments are gone but what
remains earned this burg a spot on the National Register of Historic Places.
Grab a bite at Barbara’s
on the Bay adjacent to the
beach or Marzella’s
by the Bay on your way into
or out of town.
A Nostalgic Stroll
Heading away from Betterton on Main Street, the road meanders
through the rural landscape, changing names a few times along the way,
eventually becoming SR 298 or Lambs Meadow Road. When it intersects with SR 292,
otherwise known as the Augustine Herman Highway, continue eastward on 292 and
you’ll soon intersect yet another Main Street in the colorful, inland town of Galena.
Fuel your picturesque stroll of their dogwood-lined, white-picket
fenced sidewalks with an ice cream cone or a sugary treat from Oh
So Sweet Confectionary. Or, get hearty sustenance like authentic Mexican food at Las
Marias, fresh-baked
pizza and pastas at Galena
Pizzeria or homestyle
comfort fare at Twinny’s. You’ll need it to browse the eclectic antique stores along
the way. Then, stock up for your ongoing journey at Cross Street Food and Garden,
a country market with fresh, locally sourced products.
An Organic Ramble
Near the county’s eastern border with Delaware and at the headwaters
of the Chester River, aptly named Sassafrass and Cypress streets comprise Millington’s town center. From an aerial view, this verdant
community appears a patchwork of green, while from the road its tall bulbous
water tower and the looming grain elevators of Mountaire Farms stand as
landmarks to its agricultural traditions.
Even the color of its buildings—mint, candy apple red, mustard and
cream—suggest a proclivity toward food production. Outfitted with everything a
proper town needs (a laundromat, hardware store, pharmacy, bank, schools and
places of worship), visitors will want to stop off at the Old News Memorabilia
and Collectibles to search for sentimental treasures, Fresh and Fancy from the
Farms for local goat cheese, and Calico Fields for everything lavender. Hungry
yet? Grab a slice at the Pizza
House or Millington
Pizza, or enjoy the
ever-changing, seasonal menu of farm-to-table fare at Two
Tree Restaurant.
Surprisingly,
Main Street makes the Top 10 list of street names in only 20 U.S. states, but
the ideals of main street America live in the minds of every American, perhaps
even more so with the residents of Kent County, Maryland.
Plan your visit today.
Click here for the published version.
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