Places To See & Go....Kent County, MD

A History Buff’s Guide to Exploring Kent County, Maryland

Kent County, Maryland

If you are a history lover who enjoys travel that can be infused with rich historical experiences, Kent County is your next dream destination. Nestled into a perfect spot on the Upper Eastern Shore of the Chesapeake Bay, this waterfront destination features remarkable highlights sure to pique the interest of any history buff. Surrounded by the preserved natural beauty of sweeping fields and stunning water views, a history buff cannot help but feel the familiar desire to explore stories of the past, and in Kent County, that desire is sure to be satisfied. Walk the tree-lined brick sidewalks of one of the oldest Mid-Atlantic ports of entry. Explore monuments and museums at your own pace, and without the rush of busy crowds. Immerse yourself in the history of Kent County.

To help get started on your history-driven tour of Kent County, we have assembled this guide. Make sure to visit kentcounty.com to check for additional events and activities before your visit. The opportunities to immerse yourself in the history of this region are as vibrant as they are unique, and we don’t want you to miss a single thing.

Here are 10 must-see historical highlights to get you started on your History Lover tour of Kent County.

1. Bordley Center
    301 High Street
    Chestertown, Maryland

An excellent first stop on a heritage visit to Kent County, Maryland, is the headquarters for the Historical Society of Kent County. The Bordley History Center, located in Historic Downtown Chestertown, is the unequivocal epicenter of Kent County history, home to numerous artifacts, documents, photos, publications and other items that document the area’s past. The Bordley is an impressive facility with a research library, museum space, and genealogical and archival spaces.

The Historical Society of Kent County is very active locally, offering a variety of programs and activities throughout the year for members and visitors interested in learning about Kent County’s history. The society organizes History Happy Hours held at 4 p.m. on the first Friday of the months, inviting history lovers inside the Bordley to listen to lectures and seminars, participate in discussions and enjoy delicious wine.

The society also plans the annual Chestertown Historic House Tour each fall, opening up a selection of private residences in Chestertown’s National Landmark Historic District—home to more 18th-century homes than any other Maryland town outside Annapolis—for viewing. The tour has been taking place annually for close to 50 years. Visiting in October? The Historical Society hosts Ghost Walks on multiple weekends around Halloween blending local history and lore in candlelit tours of Chestertown. Other events include monthly Bordley Brown Bag lectures and private tours that can be organized for visitors and groups.

2. Emmanuel Church
    101 North Cross Street
    Chestertown, Maryland

While the date of the first church on this site is not known for certain, it is known that it was established before a 1720 rebuilding that brought about the first brick structure. Later, in 1767, a third structure was erected. It still stands, serving as the nave of the present church. It was here, in November of 1780, during a meeting of the Anglican clergy from parishes in Kent and Queen Anne’s counties, that The Reverend James Jones first moved that what had been known as the Church of England now be called the Protestant Episcopal Church. Nine years later, the church adopted this name for the American branch of the Anglican Church. Today, visitors to this building on North Cross Street can see the memorial tablet, carved in England, in the north wall of the church, as well as the Tiffany window in the south wall—the last remaining of the patterned stained glass added to this building as part of a reconstruction in 1880.

Kent County is home to a number of historical churches and cemeteries. The churches include Christ Church IU Parish in Worton, Janes United Methodist Church in Chestertown, Saint Paul’s Parish just outside Chestertown and Shrewsbury Parish in Kennedyville. Along with churches, visiting Kent County’s historic cemeteries offers an interesting way to explore Kent County’s past. Historic headstones populate Wesley Chapel Cemetery at Wesley Chapel of Rock Hall’s United Methodist Church. In addition, the open area between the Rock Hall Municipal Building, St. John's Catholic Church and the Rock Hall Elementary School is home to several 19th-century graves at St. John's Catholic Church Cemetery, with additional historical graves near Asbury United Methodist Church Cemetery.

Located on a 19-acre site just outside of Chestertown, where some graves date as far back as the 17th Century, St. Paul's Episcopal Church Cemetery reflects one of 30 Anglican parishes established in Maryland in 1692 after William and Mary ascended to the English throne. Additional burial sites with historic ties include Holy Trinity AME Church’s Edesville Church Cemetery, near the center of Edesville, andMount Pleasant Cemetery, just north of the village of Fairlee.

3. Sultana
    200 South Cross Street
    Chestertown, Maryland

The Sultana Education Foundation of Chestertown seeks to provide individuals of all ages the opportunity to learn about and explore the Chesapeake Bay. One of the most exciting ways for the history lover to accomplish this is to set sail on the Schooner Sultana, a replica of a Boston-built merchant vessel that served in the British Royal Navy from 1768 to 1772. Due to the fact that the Sultana’s reproduction was based directly on a 1768 survey of the original schooner, it is one of the most accurate 18th-century replicas in the world today.

A sail on the Schooner Sultana includes the opportunity to experience the open water from aboard this replica ship and allows guests to help raise the sails, steer using the seven-foot long tiller and explore the authentically reproduced crew’s quarters below deck. Don’t forget to check out the Sultana Education Center and the Sultana Foundation’s other events and activities including Downrigging weekend, public paddles, summer programs and more.

4. Sumner Hall
    206 S. Queen Street
    Chestertown, Maryland
    Contact:410-778-3222

This must-visit stop in Kent County offers visitors the opportunity to explore the area’s African-American history. The Charles Sumner Post #25 of the Grand Army of the Republic was built in 1908 and served as a community center and hub of African-American life on the Eastern Shore of Maryland for more than six decades. Thanks to a 10-year restoration effort by preservationists and philanthropic citizens, it opened to the public as a museum and event venue in 2014. It is now one of only two remaining African-American veterans’ halls in the United States and it is the only G.A.R. house visitors enter. Its exhibit, “The History of Emancipation in Kent County, Maryland,” depicts local struggles for equality among African-Americans who arrived here as slaves.

Visitors interested in further exploring African American history for this region should consider a visit to the African American Schoolhouse in Worton. They may also be interested in the self-guided African American History Tour of Kent County and Maryland’s Underground Railroad Network to Freedom, which features a site in Kent County.

5. Caulk’s Field
    Caulk’s Field Road (off of Route 20)
    Chestertown, Maryland

The site of the Battle of Caulk’s Field is recognized as the best preserved War of 1812 battlefield in Maryland. The battle that took place here occurred in late August of 1814. Three days before the Battle of Caulk’s Field, in an interesting military twist, American Col. Phillip Reed misled British troops about the size of his forces, between Eastern Neck Island and nearby Trumpington Manor, by having his cavalry cross and re-cross the water in a ferry scow with such frequency that British officer Sir Peter Parker believed they occupied the entire coast. You can get a better view of this area today on Eastern Neck Island.

Around this time, the British started a more offensive posture in the ongoing war, and troops made landfall on the Bay’s shore, encountering local militia at Caulk’s Field. Cannon fire boomed and muskets crackled during this fierce battle between British and American soldiers, and the British leader, Sir Peter Parker, was killed. This great American victory provided a much-needed morale boost that led to the victory at Fort McHenry. Today, you can visit a monument at the edge of the 300-acre property, as you take in one of the most pristine battlegrounds remaining along the Eastern seaboard.

To learn more about the War of 1812, which was actually an almost three-year war lasting until February 1815 between the United States and the British Empire and its allies, check out the Star-Spangled Banner National Historic Trail. Kent County is dotted with important memorial sites on this trail where you can learn more about this important War in early American history. Other important commemorative sites on the Star-Spangled Banner National Historic Trail include Fairlee Creek, Swan Creek, Turners Creek and Christ Episcopal IU Church Cemetery in Worton, where you can see the grave and headstone for Col. Reed, who commanded the American Militia at the Battle of Caulk’s Field. One of Kent County’s best-known 1812 military leaders, this Revolutionary War hero achieved the rank of infantry captain before serving in the State house of delegates, the U.S. Senate and the War of 1812.

6. Massey Air Museum
    33541 Maryland Line Road
    Massey, Maryland

Massey Air Museum is located in the small community of Massey, Maryland. This living airport-museum is reminiscent of rural airports of a bygone era and offers visitors the chance to explore a collection of vintage aircraft, artifacts, reading materials, and touch and feel exhibits. Visitors can watch current restoration projects, walk inside the DC-3 and take tours of the airport hangars.There’s no better time to visit Massey Air Museum than during the Antique Fly-In every June. In 2016, more than 75 show and guest airplanes, including a restored 1930 Davis D-1K, landed on the 3,000-foot grass runway. Any other time of year, don’t miss the opportunity to just sit and watch the airplanes come and go.

7. Captain John Smith Historic National Water Trail
    200 South Cross Street
    Chestertown, Maryland

Roughly 400 years ago, the Englishman known as Captain John Smith, along with a small crew of adventurers, journeyed out onto the Chesapeake Bay to explore the unknown in search of the fabled Northwest Passage. Between 1607 and 1609, Smith and his crew mapped nearly 3,000 miles of the Chesapeake Bay and rivers and documented American Indian communities. His maps and writing brought transatlantic commerce to the region and gave his native England a foothold in the New World.

Visitors can embark on the Captain John Smith Chesapeake National Historic Water Trail, which received its designation in 2006, and graces Kent County at Eastern Neck Island, or venture out along the Sassafras River Water Trail or Chester River Water Trail. These paddling excursions blend heritage travel with the great outdoors and invite visitors to experience historical adventures. For more information on these water trails, visit smithtrail.net or sultanaeducation.org.

8. Rock Hall Marine Restoration and Heritage Center
    21083 Chesapeake Avenue
    Rock Hall, Maryland

Rock Hall, Maryland, settled in 1706, is known as the “Pearl of the Chesapeake.” This waterfront town has a long history of maritime industries. Watermen and their families have worked the Chesapeake Bay for generations bringing in blue crab, oysters, rockfish and more. The history of the watermen and the maritime industries is a crucial part of the story of Kent County. The Rock Hall Marine Restoration and Heritage Center is a facility that collects, preserves and exhibits boats and other objects related to this history.

Additionally, Rock Hall is home to the Watermen’s Museum, the Rock Hall Museum and Tolchester Beach Revisited Museum. Visitors may also enjoy visiting the Rock Hall harbor where panels feature information related to the work of the watermen and the Chesapeake Bay.

9. Knocks Folly and the Kent Museum
    13761 Turners Creek Rd
    Kennedyville, Maryland

Knocks Folly Visitor Center is a historic home located in Kennedyville, Maryland. This unusual structure combines a log cabin, built in 1759, with a federal style brick home, which was completed in 1796. The structure is less than a mile from Turners Creek Landing and the Sassafras Natural Resources Management Area. Here visitors can find exhibits highlighting the region’s agricultural heritage. You can also explore the region’s Native American history, specifically that of the Tockwogh tribe. Not far from the Knocks Folly Visitors Center is the Kent Museum. The collection on display here represents the rural heritage of agriculture and domestic life of Kent County as well as further information on the region’s Native American tribes and culture.

10. Betterton Heritage Museum and Betterton Beach
     100 Main Street
     Betterton, Maryland

Betterton Beach is a five-acre waterfront, family-oriented park located just 12 miles north of Chestertown. Originally a fishing village, Betterton developed into a booming beach resort community for steamboat travelers from Baltimore and other cities. Now this peaceful beach haven offers visitors a relaxing refuge on the Chesapeake Bay surrounded by a quiet sense of yesteryear. Indulge your history-seeking side by visiting the Betterton Heritage Museum, where you will see memorabilia from the town’s origins as a fishing village in the 1700s through its heyday as a resort center a century later. On display are historical artifacts, hand carved decoys, Betterton keepsakes and more.

Enjoy these places, take lots and lots of pictures. Stop for breakfast, lunch and dinner. Say Hello to all the people in the Nicest Places on Earth....Take it all in❤️

Old Stories of Rock Hall

The People, The Families and Friends, The Water, The Animals, The Stores, The Firehouse, The Schools, The Boats, The Beach, The Marsh, The House's, The Best Little Town of Kent County, MD. Chesapeake Living At It's Finest....

The Inside Scoop on the Chesapeake Bay — Adventure. Fun. Chillin' Out.

Rock Hall

Rock Hall is a fishing village carved out of a marsh. That marsh can be both beautiful and isolating as it’s on a peninsula jutting out of the eastern shore of the Chesapeake Bay. The peninsula points west, making for some amazing sunsets, and at night, the lights of Baltimore shine across the Bay.

Marshes surrounding Rock Hall

The town began in 1707 as a tobacco port at what was then called Rock Hall Crossroads. The crossroads (Main Street and Rock Hall Avenue) is the only place you’ll find a traffic light in the small town. That light is often the starting point for directions in town.

After tobacco used up the soil, the community became known for fishing and crabbing. Today, it’s a hub for docks and marinas that encapsulate the peninsula. Many marinas have inns and rooms for those who travel by land. And the marinas can be an attractive getaway, with swimming pools and small intimate restaurants.

Downtown

Downtown Rock Hall

Downtown Rock Hall is inland, well away from the shore, and goes a few blocks along North Main Street. Much of it consists of historic buildings, several of which are barely hanging together.

But in attempt at modernizing, the community has constructed a Rock Hall Village near the traffic light, consisting of small free-standing shops. You’ll also find the Rock Hall Visitor’s Center there.

What to do there? Aside from the festivals, it’s quiet. Visitors go Rock Hall for a relaxing weekend of strolling about and sunsets or an outdoors weekend of kayak, sailing, crabbing, fishing and/or hunting

Durding’s Store, circa 1925

Inside Durding’s Store

A must-stop for many boaters is the historic ice cream shop in Durding’s Store (5742 North Main Street). The store has the original 60-year old marble and stainless soda fountain where teenage “soda jerks” still hand-scoop milk shakes behind the counter. The 100-year old store also contains original “penny candy” and drug counters, and sells cards and gifts.

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Shopping

Shops on Main Street. The Mainstay (right) is a theater.

Quaint shops are scattered throughout the community. The biggest cluster is along Main Street and by the traffic light.  Those include antique, crafts, clothing and gifts. Some unique shops are stashed just off  Main Street, down a nearly hidden walkway on the side of The Mainstay (the local music hall).

There are also shops tucked into the neighborhoods, and some that combine marine supplies and gifts can be found at marinas, or along the roads to the marinas. Many of those are along Rock Hall Avenue, the main road down the peninsula toward the beach.

There are not a lot of them, so don’t expect a day of shopping. But storeowners have an interesting selection of unique items and marine-themed gifts.

Longtime visitors say there used to be a more vibrant crafts and artisan shopping experience, but it was knocked-down during the recession. The Greater Rock Hall Business Association is working to bring it back.

Several of the shops close during winter, so check times.

Bayside Foods is the downtown grocery store, which also sells wine and beer. It offers free pick-up and delivery for boaters docked at a Rock Hall marina (open daily 7am-10pm).

Activities/Beach

Ferry Park beach

There is a public swimming beach on Beach Road. It’s called Ferry Park, although no ferry goes from there anymore.  It has a short boardwalk with benches, grills and a gazebo, and is known for great sunsets. To get to the beach, continue west to the end of the peninsula on Rock Hall Avenue. There are signs pointing to the beach.

Kayaks on Ferry Park beach

Rock Hall is mainly known for boating. Kayak and small boat rentals are available. Charters are available for fishing and crabbing excursions. In the fall, the area turns to duck and geese hunting. Excursions are available for that too.

To draw in visitors during the summer and fall, the town holds a number of special events. That’s when Rock Hall comes alive. Independence Day fireworks and Waterman’s Day in July, Pirates and Wenches Fantasy Weekend in August and Fall Festival in October are the largest. The town closes Main Street and local artisans & merchants set up booths.

To make Rock Hall a weekend getaway outside of the events and festivals, you should be ready for a quiet, relaxing time away from home.

Food & Libations

Here’s a list of Rock Hall’s restaurants.

Waterman’s Crab House in Rock Hall

The biggest & best-known bar is Waterman’s (21055 Sharp Street), a crab shack that has turned into a huge outdoor bar and gathering place for boaters. It has bands or karaoke on most weekends. Waterman’s has its own docking area for boats (2-hour limit on docking). There’s air conditioned, slightly more formal dining inside and picnic tables for casual dining outside by the water.

There’s also the Harbor Shack (20895 Bayside Avenue), which really is a waterside shack with a large deck in a marina. It’s a big, roomy casual place with a sense of humor, and features traditional Chesapeake Bay bar food — seafood, burgers and sandwiches. The bar features bands on the weekends and there’s an outdoor tiki bar by the water. .

Bay Wolf Restaurant

Bay Wolf, (21270 Rock Hall Avenue) is a smaller, intimate place. It provides an inexpensive lunch menu and a higher-priced, more formal dinner menu featuring gourmet seafood choices.

None are close to each other. All are highly recommended by many. They welcome, but don’t necessarily cater to, visitors; you should be ready to accept them in their localness. And don’t be in a hurry.

The Mainstay

The Mainstay is a 120-seat concert hall downtown, known for jazz bands, but also hosts other music and plays. Seating in the 100-year old building can be a straight chair, wicker armchair or sofa. It’s run by a nonprofit group, and the website says there’s not a bad seat in the house; meaning for sight and sound, but the comfort of the seats can vary depending on how lucky you are. All seats are general admission.

Some performances are free (donation requested for local causes), but tickets vary depending on the act. The concession offers beer, wine, soft drinks and home-baked goods. Check their website for schedule information.

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Museums/History

The town has three museums, each offering a unique experience.

Rock Hall Museum (Municipal Building, South Main Street) is off Main Street and focuses on community lifestyle and traditions. A special feature is its decoy carving section, showing the work of master carvers. The museum is located in the Municipal Building and is open weekends 11am – 3pm & by appointment.

Waterman’s Museum

Waterman’s Museum (20880 Rock Hall Avenue) explains the life of professional fishermen, who on the Chesapeake Bay are called “watermen.” The sign on the door says it’s open daily (except winter holidays) from 10am – 5pm. But you have to get the key from the business next door; the museum operates on an honor system.

Tolchester Beach Revisited Museum in Rock Hall

Then, there’s Tolchester Beach Revisted,  a museum about a late 1800’s  amusement park that once dominated the region.

Tolchester started before Rock Hall, down the shore a bit. It eventually became an amusement park in 1877, the most popular beach resort on the Bay. You should go to the museum to learn the rest of the story. The museum is behind The Mainstay on  Main Street in downtown Rock Hall. It’s open Saturday and Sunday, 11am – 3pm.

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Getting Around

By Land

Rock Hall is much easier to get to by water than by land. When the village began, the only mode of transportation was boat. Now, it’s long, but scenic, drive across rivers and down the peninsula.

It’s pretty sleepy when there are no events, so street parking is easy to find and there are a number of parking lots.

During festivals, parking is well organized near the events a short walk away. But close-by parking will fill-up. The community provides shuttles to the venues, usually a $1 donation per person. There are specific shuttle stop locations, but they often will pick up people who flag them down if there’s room.

During Pirate’s weekend, shuttles fill-up fast and the wait can seem long, but nearly everyone is in a good mood so getting to know your fellow stand-bys is a good time until the shuttle comes around.

Many people get around by walking or riding bikes, but it can be a long walk. For example: it’s a little more than a mile from downtown to the beach, and about a half-mile from downtown to Waterman’s restaurant. For those not wanting that much exercise, bikes can be rented at some marinas.

By Boat

The channel is narrow and boaters need to keep a sharp eye out for markers. Sailboats, especially, are known to plow into shallows and have to be towed out or wait for high tide. The Rock Hall harbor was dredged in 2013 to a minimum depth of seven feet below low water and now follows the Coast guard marked channel straight out of the harbor.

Blue Crab Chesapeake Charters

Blue Crab Chesapeake Charters

Rock Hall Harbor

Rock Hall, MD 21661

(410) 708-1803

bluecrabcc@aol.com

Sailing on the Chesapeake Bay-Maryland's Eastern Shore

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Home of Rock Hall's Original Sunset Cruise 

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Rock Hall Journal: Town's Revival Is Feared As A Peril To Its Charm

Sunset on the beach in Rock Hall, MD. will take your breath away 

and they are so different each evening.

     It started with a sunset four years ago. ''A gorgeous sunset,'' said Arlene Douglas. After breaking his arm, her husband, Tom Sabol, a real estate lawyer in Philadelphia, could no longer work on the old boat he just bought. So they spent a Sunday afternoon in August driving around Maryland's Eastern Shore. Somehow, Ms. Douglas said, they ended up in Rock Hall, a 290-year-old town of 1,600 that has sent watermen into Chesapeake Bay for generations.
     Driving past the town's small public beach, the couple stopped to watch the sun disappear over the bay and, as Mr. Sabol recalled, ''we fell in love with the place.'' Then they started buying it. First, it was ''a shack'' across from the beach that they made a weekend hideaway. Next they turned a long-dormant general store ''Frank Kline's: The Big Store With the Little Prices'' -- into the America's Cup Cafe, a coffee shop, which grew to include a bookstore, which grew to include a restaurant, which sells Miss Virginia's crab cakes, reputed to be the best on the bay.
     Then Mr. Sabol began scouting around Kent County for old, unused wooden buildings, which he transported to a lot adjacent to the cafe. Spruced up, the structures provide exhibit space for artists like Bob Powitz, who works with driftwood, and Jane Hackett, who paints. Next to the cafe, the couple helped turn an old grocery into a 146-seat theater that features live concerts from February through October.
     And all along the 200 yards of Main Street between Rock Hall's two traffic lights are other signs that the commercial center is popping back to life -- quaint new shops, refurbished restaurants and a growing artists' colony -- reminding old timers like James Culley, a 78-year-old waterman, of when a beer on Main Street cost a dime. It is all dazzling to Ms. Douglas. ''It's just a beautiful place to drive around, with the marshlands, the wetlands and the bay,'' she said.
     Rock Hall is beautiful, all right, enough so that on most summer weekends the head count more than doubles with increasing numbers of tourists and pleasure boaters from Washington, Baltimore, Philadelphia and southern New Jersey and that is beginning to worry some of the town's residents.
     Rock Hall's rejuvenation has come at a time when the bay's fishing industry is in slow decline because of state-mandated limits, pollution and a diminishing supply of fish. But it has also brought about rising real estate prices, crowded sidewalks and more traffic, prompting some people to wonder whether economic development might cost Rock Hall part of its charm, much in the way that places like New Hope, Pa., and Carmel, Calif., were discovered by outsiders, then overwhelmed.
     ''You should see all the chicken-neckers down here,'' said Jennifer LaPore, 18, a cook at the Rock Hall Snack Bar, using a colloquial expression for out-of-towners. (Visitors use chicken necks for bait; locals prefer eels.) ''They spend money and think they own the place.'' ''And they can be rude,'' said her friend Tammy Hawkins, 19.
     Returning from the bay on his 60-year-old boat, Go Girl, with bushels of blue crabs, Mr. Culley said even local watermen were feeling the pinch of warm-weather visitors, many of whom moor their boats in the same marinas that watermen use and take them into the same areas where watermen are working.
     ''It's a little bit too many out there for me,'' Mr. Culley said. ''Used to be a pretty quiet town. Now it's like everywhere else.''
     Al Cornelius, 57, is a fourth-generation waterman who was born in Rock Hall and steered his two sons away from continuing the family tradition. Both are local house painters, and he is just as happy. ''It has really changed in the last seven or eight years with more city people moving in,'' Mr. Cornelius said. ''You can't stop progress, but I liked it the way it was years ago, when you knew everybody by name, every family.''
     Ronald H. Fithian, the town manager, sees no cause for alarm just yet. With Rock Hall's protected harbors long known to watermen and boaters, virtually all the local marinas are full, he said. And few lots in town are available for improvement. ''We're almost to the point where everything that could be developed has been developed,'' Mr. Fithian said. That is not necessarily the case just beyond the town's northern limits on an undeveloped tract across Swan Creek, where a developer has proposed building a golf course, conference center and vacation villas.
     The developer, Tim Wyman, who is president of the B.A. Charters Corporation, said the project would create the kind of jobs that attract young people to Kent County, the least populated of all Maryland counties since 1960. It would also, he said, provide more permanent stability to an economy that, until the recent boom in tourism, relied mostly on fishing and agriculture. However, even recognizing that some longtime residents might object to the changes along Main Street that she and her husband have initiated, Ms. Douglas wondered, ''How much do we really need?''
     ''More business doesn't mean the quality of life is improved,'' she said. ''If I can go to the grocery store or gas station and say, 'Oh, I forgot my wallet,' and the guy says, 'So pay me tomorrow,' that's where I want to live. That's how it is here now, and I would hope that doesn't change.''