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Charming Main Streets of Kent County (travel article)


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.

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