Talbot County is home to some of the most beautiful and historic small towns in America. Explore our culinary treasures, one-of-a-kind boutiques, and elegant inns. Or bike, kayak, and sail the Chesapeake Bay.
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COUNTY
Talbot County: Tradition takes center stage
In the 1960s, Talbot County faced a choice. A series of poor crab and oyster harvests, caused by diseases that infiltrated the Bay, forced packing houses to shutter their doors. The skipjack fleet collecting oysters by sail was widely perceived to be running on borrowed time. Most steamboat routes had been discontinued.
On the brink of economic depression, the Talbot County community needed to decide what was next. The crisis launched a movement to celebrate and preserve the area’s history and traditions.
For a dedicated group of historical society members and community volunteers in St. Michaels, the solution came in the form of the Chesapeake Bay Maritime Museum.
“Part of the vision of the founders here was the sense that the Chesapeake Bay was changing, and it was changing fast,” said Pete Lesher, the museum’s chief historian and a Talbot County Council member.
In ushering in the new era, these volunteers held a paramount principle — the story of Talbot County, and of the Bay more broadly, must be told for generations to come.
Lesher says that principle still guides the museum and the community today. Today, Talbot County is a vibrant tourist destination known for its thriving
^ The Antique and Classic Boat Festival and Coastal Arts Fair is held at the Chesapeake Bay Maritime Museum in June.
culinary, arts and cultural scenes, all of which carry a pride in the region’s tradition.
The county is home to institutions and events where that tradition takes center stage, like Easton’s annual Waterfowl Festival, which began as a humble community effort to raise conservation funds for Bay ecosystems in the 1970s. The event has since evolved into a sprawling showcase of Eastern Shore culture, though it has not lost its conservation mission.
“So everybody loves the Waterfowl Festival,” said Deena Kilmon, the festival’s executive director and a longtime Talbot County resident. “Unless you’ve really — and I mean really — been an insider volunteer, you’ve probably never asked yourself why we’re here… The founders were hunters, so they were closely affiliated with other conservation groups that said, ‘If we don’t save the lands, we can’t hunt them.’
“... The culture of the Eastern Shore is they’ve always needed these open spaces — for commerce, for food, for sustenance and now for recreation as well.”
And along with celebrating local tradition, for many Talbot County residents, the festival has become a tradition in its own right.
“In addition to performing our mission, it has become somewhat a celebration of who we are,” Kilmon said.
Photo
George Sass
A STORIED PAST
Founded around 1661, Talbot County is named for Lady Grace Talbot, sister of Lord Baltimore and the first proprietary governor of Maryland. From its beginning as an English colony, products of the Bay and agriculture have always provided Talbot County’s chief sources of income.
It has been home to many who shaped not only local history, but American history, including names that have surprised even longtime locals.
The first time Harriette Lowery heard that Frederick Douglass had grown up in Talbot County was when she moved back to Easton with her husband in the early 2000s.
Lowery was surprised to hear of Douglass’ local origins. She had grown up in Talbot County, but she had never known it was the famed abolitionist’s birthplace.
< Sean Mann of Sean Mann Outdoors teaches kids the skill of goose & duck calling at the Waterfowl Festival in 2024.
Born in Talbot County in 1818, Frederick Augustus Washington Bailey Douglass was enslaved for 20 years on Talbot County farms and in Baltimore. He fled north in 1838 and changed his name to Frederick Douglass. His brilliance, eloquence and courage brought him to the forefront of the abolitionist movement.
For Lowery and many others, discovering Douglass’s roots in Talbot County inspired action.
“The historical society had put a notice in the paper asking for people to respond to a question: ‘Is anybody interested in honoring Frederick Douglass in some way since he’s our native son.’ And I read that and thought, ‘I knew a lot about Frederick Douglass, but I did not know he was from Talbot County,’” Lowery told The Star Democrat in September. “... I was a little embarrassed by that but more interested in doing something because of that.”
Lowery and her late husband became founding members of the Frederick Douglass Honor Society, the group that spearheaded the process of having a statue of Douglass erected on the Talbot County Court House lawn. The group now hosts an annual celebration in September honoring Douglass’ legacy.
Along with Douglass, Talbot County has been home to famed war heroes, musicians, artists and businesspeople, each contributing to the fabric of a continually evolving community.
The completion of the Bay Bridge in 1951 marked the end of the Eastern Shore’s isolation. The changes that followed brought economic benefits through travel and tourism — but also raised concerns about preserving the past.
The community has taken up the mantle of making sure Talbot County’s history is not lost as the area navigates future changes. “The story
< An oyster tonger welcomes visitors to the Chesapeake Bay Maritime Museum in St. Michaels.
Photo by Konner Metz/Star Democrat
has not stopped, and that’s very much a piece about who we are today,” Lesher said.
EXPERIENCE THE HISTORY
The following is a taste of places and activities you can enjoy as you get to know a county rich in history, tradition and culture.
Easton, hub of the community
Nestled in an agricultural setting, Easton is the vibrant county seat and boasts about 17,000 residents who enjoy a sophisticated arts community, a diverse culture, waterfront dining experiences and so much more.
Easton is home to the busiest airport on the Delmarva Peninsula, golfing and water sports, art galleries, concerts at the historic Avalon Theatre, shops for every taste, hospital and medical centers, a variety of schools, houses of worship and hundreds of nonprofit organizations.
To learn more, visit eastonmd.org or discovereaston.com.
Frederick Douglass Driving Tour
The American patriot was born in 1818 on Tuckahoe Creek in Talbot County. Born to an enslaved mother who named him Frederick Augustus Washington
v A statue of Frederick Douglass stands over a crowd at the Frederick Douglass Day welcome ceremony on the Talbot County Court House lawn in 2024.
Photo by Wendy Weitzel/Star Democrat,
Bailey, he was part of the sixth generation of Baileys in Talbot County — a lineage that continues today. For a wealth of information about Talbot’s native son and maps of a driving tour of significant places, visit frederickdouglassbirthplace.org.
Oxford, a village of quiet elegance
A scenic drive or a short voyage on what is believed to be the country’s oldest privately owned ferry will guide you to the quiet village of Oxford.
Oxford is one of the oldest towns in Maryland and is listed on the National Registry of Historic Places. Collect beach glass along The Strand, have a picnic in the public park on the Tred Avon River or just step back in time strolling the streets and lanes.
Learn more at portofoxford.com.
St. Michaels, thriving then and now
Once a thriving Colonial town that “fooled the British” during the War of 1812, St. Michaels now boasts the world-class Chesapeake Bay Maritime Museum and working shipyard, as well as numerous waterfront eateries and shops. Explore the beautiful waterways and scenic views, and relax at a quaint inn or bed and breakfast. In the old mill district, you’ll find a brewery and distillery that serve awardwinning libations.
Download a brochure at tourtalbot.org or visit stmichaelsmd.org.
The
Hill Community Walking Tour
Easton’s Hill Community has been home to free African Americans since the 1780s, more than 80 years before the Civil War ended in 1865.
In 2020, The Hill Community Project designed wa tour that helps neighbors and newcomers alike to explore the lives of the still-vibrant community that celebrates a rich heritage of courage, community, faith and enterprise.
Download the map at thehillcommunityproject.org.
v Kaitlyn Hay paints the turquoise facade of the Chesapeake Blooms building during the 2024 Plein Air Easton Quick Draw competition.
Queen Annes
COUNTY
Queen Anne’s County: Gateway to Eastern Shore
From its earliest inhabitants to its presentday status as the gateway to the Eastern Shore, Queen Anne’s County has played a vital role in the history of Maryland. Today it stands as a destination for visitors seeking a blend of relaxation, adventure and culture, offering everything from outdoor adventures to waterfront dining and a step back in time through the area's rich heritage.
Queen Anne’s County was established in 1706, named for Queen Anne of Great Britain, who reigned from 1702 to 1714. The county’s formation coincided with a period when Maryland was a royal colony. Historic sites throughout Queen Anne’s County reflect its significant past, from Native American settlements to colonial structures and Revolutionary War-era landmarks. But this county is not just about looking back — it’s about embracing a lifestyle that’s as exciting as it is laid-back. Whether you’re relaxing on the beach, exploring miles of trails or enjoying fresh seafood by the water, Queen Anne’s County offers something for everyone.
HISTORIC CHARM
Begin your journey in the heart of Queen Anne’s County: the town of Centreville. Founded in
1708, Centreville is a charming town that reflects the area’s rich history through its well-preserved architecture and public spaces. Stroll down the streets and you’ll find an array of historic buildings, quaint shops and cozy cafes, each offering a glimpse into the past.
A must-visit is the Queen Anne’s County Courthouse, a building steeped in history and still functioning today. Nearby the Centreville Historic District includes homes and churches dating to the 18th and 19th centuries, each telling a story of the town’s evolution from a colonial port town to the county seat.
For a deeper dive into the area’s history, the Chesapeake Heritage and Visitors Center in Kent Narrows is a great spot to start. The center offers exhibits on the area's Native American history, maritime heritage and the role Kent Island played during the colonial and Revolutionary War periods. Or visit the Wye Mill — the oldest continuously operated grist mill in the United States — it is the earliest industrial site on the Eastern Shore in continuous use, dating to the late 17th century.
OUTDOOR ADVENTURES
Queen Anne’s County is a haven for outdoor
^ Kent Narrows, Kent Island
enthusiasts, offering a wide array of activities for visitors looking to experience nature. From hiking and biking to fishing and kayaking, the county’s landscapes are perfect for those who enjoy exploring the outdoors.
The Cross Island Trail, which stretches across Kent Island, is a popular destination for walkers, joggers and cyclists. This 5½-mile trail provides scenic views of the bay, marshes and woodlands, making it a perfect spot to soak in the natural beauty of the area.
Along the trail, you’ll find several parks and picnic areas, perfect for a family outing or a relaxing afternoon in nature.
If you prefer to explore the area by water, there are several kayak and stand-up paddleboard rental
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businesses on Kent Island. These rentals offer guided tours and group experiences, making it easy to experience the beauty of the Chesapeake Bay up
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^ The Queen Anne statue holds court with event festivities in the background.
close. Whether you’re interested in a peaceful paddle or a more adventurous tour, the waters around Queen Anne’s County provide the perfect backdrop.
For a more leisurely activity, consider visiting one of the county’s picturesque beaches. Ferry Point Park, located near the Kent Narrows, is a great place to relax and enjoy the views. The park features 41 acres of tidal and non-tidal wetlands as well as uplands. A variety of wildlife can be observed while taking in the scenery along the one-mile unpaved trail that ends at a sandy shoreline. Surrounded by three bodies of water (Chester River, Kent Narrows and Piney Creek) the scenic views are magnificent.
FESTIVALS AND EVENTS
Queen Anne’s County knows how to celebrate, with a variety of events throughout the year that showcase the region’s culture, arts and local flavors. One of the most anticipated events is the Independence Day celebration, set to return on July 2 at the Chesapeake Heritage and Visitors Center in Kent Narrows. This beloved event features free family activities, food trucks and a stunning fireworks display over the water, making it the perfect way to kick off the summer.
For those visiting during the spring and summer, there are numerous festivals celebrating local crafts, music and food. The Kent Island Farmers Market at Cult Classic offers fresh produce, local goods and a taste of the community. At the Centreville Farmers’ Market shop your favorite local farmers on Lawyers Row and the Courthouse Green and find artisans,
musicians and food vendors, highlighting the best of what the Eastern Shore has to offer.
ARTS AND ENTERTAINMENT
Queen Anne’s County is home to a vibrant arts scene with local galleries and performance spaces offering a rich variety of cultural experiences.
The Kent Island Federation of Arts in Stevensville showcases works by local artists, including paintings, photography and pottery, while the Kent Island Heritage Society hosts regular events celebrating the area’s rich cultural history.
Once a historic movie theater, Church Hill Theatre, located in the charming town of the same name, is a cornerstone of the local arts community. This vibrant performing arts center is dedicated to producing and presenting high-quality theatrical performances and educational programs for people of all ages. The theater is housed in a beautifully restored art deco building.
DINING BY THE WATER
No trip to Queen Anne’s County would be complete without indulging in some of the best local seafood. The county’s location on the Chesapeake Bay means that fresh seafood is always on the menu. Many restaurants along the waterfront offer “boatto-table” experiences, where you can enjoy a meal while taking in stunning views of the Bay.
The Narrows in Grasonville is a favorite among locals and visitors alike, known for its fresh oysters, crab cakes and stunning water views. Another
^ Ferry Point Park
popular spot is The Fisherman’s Inn, located on Kent Narrows, which serves up classic Eastern Shore dishes like steamed crabs and clam chowder or try nearby Bridge's for lunch or a romantic dinner.
For casual dining and live music check out Red Eye's Dock Bar, The Jetty or Harris Crab House. Next door to Harris' is a great spot of coffee with a view and undeniably sweet treats at Dessert First. Still need something sweet, Sugar Doodles is right across the water.
15 GREAT OUTDOOR ACTIVITIES
1. Kayaking and stand-up paddleboarding on the Chesapeake Bay.
2. Biking along the Cross Island Trail.
3. Hiking at Wye Island Natural Resources Management Area. Fun fact: Wye Island houses a Holly Tree that is more than 290 years old.
4. Fishing from the Kent Island fishing pier.
5. Boating on the Kent Narrows.
6. Exploring historic Stevensville.
7. Walking through downtown Centreville.
8. Birdwatching at Chesapeake Bay Environmental Center.
9. Fishing with one of the many charter boat captains.
10. Picnicking at Terrapin Nature Park.
11. Taking a scenic drive through rural Queen Anne’s County.
12. Visiting local wineries for tastings and tours.
13. Playing golf at one of the county’s golf courses.
14. Enjoying a sunset cruise on the Chesapeake Bay.
15. Attending live music at one of the Island's Tiki bars.
Whether you’re exploring the great outdoors, savoring local cuisine or immersing yourself in the history of this charming county, Queen Anne’s County offers something for everyone. Make sure to plan your next getaway to this unforgettable destination.
This article was compiled from Queen Anne's County Tourism information and the Bay Times Record Observer archives with the assistance of ChatGPT. The story was subsequently edited and fact-checked by Hannah Combs.
^ Freshly steamed blue crabs and Old Bay are a staple of any visit to Queen Anne’s County.
> “Uncle Sam” waves at the parade audience during the annual Kent Island Day parade through historic Stevensville.
v Runners cross the Chesapeake Bay Bridge
Caroline
Caroline
COUNTY
Caroline County: Tapestry of history, beauty, culture
Nestled on Maryland’s Eastern Shore, Caroline County offers a rich tapestry of history, natural beauty and cultural experiences. From the serene trails of Adkins Arboretum to the poignant stories of the Underground Railroad, this county invites visitors to explore its unique charm.
Caroline County's economy has long been anchored in agriculture, with numerous farms producing a variety of crops and hosting seasonal events. The county's diverse ecosystems provide habitats for a wide range of wildlife, making it a prime location for nature enthusiasts.
From historic churches to preserved schoolhouses, Caroline County offers a rich tapestry of cultural landmarks reflecting its multifaceted history.
ADKINS ARBORETUM: A SANCTUARY OF NATIVE FLORA
Spanning 400 acres, Adkins Arboretum in Ridgely is a haven for native plant enthusiasts and nature lovers. As a model for land management, the arboretum engages visitors in conservation and appreciation of the Chesapeake Bay region's native landscapes. Visitors can explore diverse habitats, including meadows, forests, and wetlands, through five miles of
walking paths. The arboretum also hosts art exhibits, educational programs, and seasonal events, making it a year-round destination for all ages.
TRAILS AND OUTDOOR ADVENTURES
Caroline County boasts an array of trails catering to hikers, bikers, and equestrians. Tuckahoe State Park offers over 20 miles of scenic trails winding through hardwood forests and along the Tuckahoe Creek. Martinak State Park provides additional trails with picturesque views of the Choptank River. These trails offer opportunities to observe local wildlife and enjoy the tranquility of the Eastern Shore's natural landscapes.
ECHOES OF THE PAST
Colonel Richardson's Tomb: Located two miles north of Harmony on Route 16, Col. Richardson's tomb commemorates Colonel William Richardson, a Revolutionary War hero who led the 5th Maryland Regiment. Richardson (1735-1825) lived and is buried at Gilpin Point, Caroline County. He was a local political leader and a Revolutionary War soldier. A member of the Maryland Assembly from 1773-1776, he introduced the bill that created Caroline County
^ Martinak State Park, Denton
in 1774 and he was one of the first commissioners. In 1776, he became colonel of the "flying camp" of the Eastern Shore and fought at Harlem Heights. He was a first colonel in the 5th Maryland Regiment and helped suppress Tory activities in the lower Eastern Shore. After independence was gained, he remained an influential figure in Eastern Shore and Caroline County life.
Harriet Tubman and the Underground Railroad: Caroline County is deeply connected to the legacy of Harriet Tubman. The Harriet Tubman Underground Railroad Byway is a self-guided driving tour that spans over 125 miles through Maryland's Eastern Shore, including significant sites in Caroline County. Visitors can explore locations where Tubman lived and worked, gaining insight into her courageous efforts to lead enslaved people to freedom.
Civil War Trail: The Maryland Civil War Trail features six sites within Caroline County, highlighting the region's role during the Civil War. In Greensboro, for instance, pro-Union residents sought assistance from President Lincoln, reflecting the county's complex historical landscape during this tumultuous period.
Historic Black Schools: Caroline County is home to eight historic Black schools dating back to the post-Civil War era. These institutions, established as early as 1870, served as vital centers for education and community for African Americans during segregation. Preserving these schools offers a window into the resilience and determination of Black communities in the face of adversity.
> Artists capture the landscapes at Adkins Arboretum and then frame their works and exhibit them on their easels during Plein Air Adkins, which is held in November.
< A sign commemorating the historic election of Federalsburg’s first Black town council members was unveiled in 2024 as part of a settlement between the town and several civil rights organizations.
FEDERALSBURG RECONCILING WITH PAST
In a landmark 2024 settlement, the town of Federalsburg acknowledged a history of discriminatory voting practices that disenfranchised Black residents for over two centuries. The agreement, resulting from a federal lawsuit, includes restorative measures such as public apologies and initiatives to promote inclusivity and equity. This pivotal moment marks a step toward healing and recognition of the town's diverse heritage.
The results of the settlement can be seen throughout the town:
• An official, signed apology framed and permanently displayed at Town Hall.
• A commemorative plaque affixed to the building at Town Hall, “From Protest to Progress: Events that Changed the Face of Federalsburg”, celebrating Black voters’ historic voting rights victory.
• A photo display at Town Hall featuring Black community contributions to the Town.
• Restoring the name Brooklyn Avenue to the portion of the avenue in the Black district.
• A historical marker in the Black community of Brooklyn celebrating the contributions of the neighborhood's residents and their ancestors.
• Sept. 26 each year is Voting Rights Day in recognition of Black voters' historic win on that day in 2023, the town's bicentennial year.
• An annual multicultural celebration.
Courtesy of Adkins Arboretum
MUST-SEE ATTRACTIONS
Wharves of Choptank: Explore the historic riverfront in Denton, once a bustling hub for trade and transportation.
1. Castle Hall: Visit this historic estate near Goldsboro, showcasing 18th-century architecture and agricultural history.
2. Schrader’s Bridgetown Manor: Experience outdoor adventures, including hunting and shooting sports, at this family-friendly venue.
3. Museum of Rural Life: Discover exhibits highlighting the agricultural heritage and daily life of Caroline County's past.
4. Preston Historical Society: Engage with local history through artifacts, photographs, and stories preserved by dedicated volunteers.
5. Greensboro Museum: Learn about the town's evolution and notable figures who shaped its development.
6. Federalsburg Area Heritage Museum: Delve into the rich cultural tapestry of Federalsburg through diverse exhibits and programs.
7. Birding and Boating Byway: Embark on a scenic route ideal for birdwatching and exploring Caroline County's waterways.
8. River City Cruise Co.: Enjoy leisurely boat tours along the Choptank River, offering unique perspectives of the county's landscapes.
9. Chesapeake Ghosts: Experience guided tours that delve into local legends and haunted sites across the county.
10. Delmarva Balloon Rides: Soar above the Eastern Shore for breathtaking views of the countryside.
11. Williston Community Church: Visit this historic church, reflecting the spiritual heritage of the community.
12. St. Paul's Episcopal Church: Admire the architectural beauty and historical significance of this longstanding place of worship.
13. Camp Mardela: Participate in retreats and camps that offer spiritual growth and outdoor activities.
14. Denton Mercantile: Shop for unique gifts, antiques and local crafts in this charming store.
TWO FAVORITE FESTIVALS
Rock the Barn Music Festival: This event is held at the Cow Barn and will be held July 1 from 3-10 p.m. It features three local band talents and gives the community a place to come together, enjoy good music, shop vendors, have dinner and lots of fun.
Mactoberfest: This event features local chefs in a mac and cheese competition. Each attendee will sample a variety of cultivated dishes and vote for their personal favorite. There are vendors to shop, a DJ on site and a grand finale to announce the current year winner, the "Big Cheese." The event sells a limited number of VIP tickets, which have access to an indoor dining area with servers, a bar area, a massage room with complimentary massages and their own gift bag. This event is held at the Culinary School in Denton on Oct. 25 from 11 a.m. to 3 p.m.
HIDDEN GEM
Caroline County invites visitors to explore its scenic landscapes, delve into its rich history and engage with its vibrant communities. Whether you're hiking through lush trails, uncovering stories of the past or enjoying local festivals, there's something for everyone in this hidden gem of Maryland's Eastern Shore.
This article was compiled from Caroline County tourism information and Star Democrat archives with the assistance of ChatGPT. The story was subsequently edited and fact-checked by Jim Johnson.
v You can see the white tag on a Monarch butterfly’s wing in Jim Wilson’s hands. They fly from Canada to Mexico. The tag helps naturalists keep track of them. Wilson leads birding walks at Adkins Arboretum.
Team MEET the
DAVID ANTHONY
Multimedia Account Executive danthony@chespub.com 410-829-0561
Talbot County
CINDY TRIBBETT
Clint Solutions Specialist
Recruitment/Print/Digital ctribbett@chespub.com 410-770-4172
DONNA BAEZ Account Executive dbaez@chespub.com 954-914-9673
Queen Anne’s County
TORI PACK Inside Multi Media Account Executive
Recruitment/Print/Digital tpack@chespub.com 410-770-4173
SHANIA GARCIA-HERRERA Multimedia Account Executive sgarcia@chespub.com 410-829-3460
Kent, Caroline & Dorchester Counties
WENDY WEITZEL Managing Editor wweitzel@chespub.com
Talbot, Dorchester & Caroline Counties HANNAH
Managing Editor hcombs@chespub.com
Kent & Queen
Anne’s Counties
Dorchester COUNTY
Dorchester
Dorchester County: History, beauty and heritage
Dorchester County offers a blend of rich history, natural beauty and cultural heritage. From the legacy of Harriet Tubman to the pristine landscapes of the Blackwater National Wildlife Refuge, it's a destination that tells America's story through its people, places and traditions. The county even has its own song, "Dorchester Dreams."
Dorchester isn't about rushing from attraction to attraction. It's about watching an osprey dive for fish, savoring a crab cake on a breezy dock, talking to a local about where to find the best soft-shell crabs and learning stories that shaped the nation in a place that still feels timeless.
For anyone seeking authenticity, connection and natural beauty, it's not just a vacation — it's a discovery.
MUST-SEE ATTRACTIONS
Dorchester County offers several compelling destinations for visitors seeking history and natural beauty.
The Harriet Tubman Underground Railroad Visitor Center in Church Creek features interactive exhibits detailing Harriet Tubman's life and the Underground Railroad, providing insight into the life of a pivotal figure in American history.
^ An eagle soars over the Blackwater National Wildlife Refuge.
The Blackwater National Wildlife Refuge near Cambridge encompasses over 28,000 acres of wetlands and serves as home to diverse wildlife and migratory birds, making it ideal for birdwatching, hiking and photography enthusiasts.
The Dorchester County Historical Society in Cambridge houses the historic Meredith House, Neild Museum and Robbins Heritage Center, showcasing local history and allowing visitors to explore Dorchester's rich cultural and agricultural heritage.
^ The sunrises over the lighthouse on the Choptank River in Cambridge.
Photo by Jill Jasuta
Courtesy of Blackwater National Wildlife Refuge
ANNUAL EVENTS
The county hosts numerous events throughout the year that celebrate its diverse culture and heritage.
The Groove City Culture Fest takes place on the third Saturday in August (Aug. 16, 2025) on Pine Street in downtown Cambridge. This vibrant street festival celebrates African American heritage with live music, dance performances, art exhibits, health and wellness education and diverse food vendors, offering visitors an opportunity to experience the heart and soul of the Cambridge community through cultural expressions and family-friendly activities. The event is organized by the Groove City Black Heritage and Culture Organization, with Veronica Taylor available at 443-521-1016 for information.
Water sports enthusiasts can enjoy the Cambridge Classic Powerboat Regatta in May at Great Marsh Park in Cambridge. As one of the oldest powerboat races in the U.S., this
event features high-speed hydroplane racing on the Choptank River, providing thrilling races in a family-friendly atmosphere with a tradition dating back over a century. The Dorchester Chamber of Commerce organizes this event.
Thunder on the Choptank occurs on July 1920 at Estuary Park in Cambridge. This annual powerboat racing event features various classes of hydroplanes and speedboats and is organized by the Kent Narrows Racing Association, bringing together racing enthusiasts for two days of competitive racing on the Choptank River. Details can be found on the Cambridge Power Boat Racing Association website.
The arts community is celebrated through the Dorchester Center for the Arts Showcase, with the 2025 date to be announced. Located in the downtown Cambridge Arts and Entertainment District, this art walk and street festival features local artists, live music, dance performances and food vendors, celebrating the creative community of Dorchester County in a vibrant downtown setting. The event is organized by the Dorchester Center for the Arts.
For music lovers, the Music on the Nanticoke free summer concert series runs during the summer months at Waterfront Park in
< Food was a huge factor in the fun of Groove City Culture Fest. These folks were running a lemonade trailer.
^ A mural depicting famous women in Dorchester County history adorns a wall in downtown Cambridge.
Courtesy of Dorchester County Tourism and Heritage
Vienna. This series of free outdoor concerts features various musical genres and offers live music by the river in a relaxed, family-friendly environment. The Town of Vienna organizes these concerts.
History enthusiasts can attend Spocott Windmill Day, held twice annually in May and October near Cambridge. This event features demonstrations of Maryland's only operational post windmill along with tours of historic buildings, allowing visitors to witness a unique piece of Maryland's milling history in action. The Spocott Windmill Foundation sponsors the event and can be reached at (410) 228-7090 for more information.
IRONMAN MARYLAND
Dorchester County serves as the host for Ironman Maryland on Saturday, Sept. 20, in Cambridge. The full-distance triathlon includes a 2.4-mile swim in the Choptank River, a 112mile bike course through Dorchester County and the Blackwater National Wildlife Refuge and a 26.2-mile run through Cambridge and surrounding areas.
The event is known for its flat and scenic course, ideal for personal bests and offers 30 qualifying slots for the Ironman World Championship in Kona, Hawaii. The swim course consists of two loops in the Choptank River, starting and ending at Great Marsh Park.
The bike course is a two-loop route through Dorchester County, including the Blackwater National Wildlife Refuge. The run course comprises three loops through Cambridge, culminating at the historic Long Wharf. Registration and information are available through the Ironman Maryland website.
> Matt Tatum celebrates after winning the 2024 Ironman Maryland triathlon
^ A statue commemorating the life of Harriet Tubman is outside the Dorchester County Courthouse in Cambridge.
Photo by Jill Jasuta
Photo by Jim Johnson/Star Democrat
IRONMAN 70.3 EAGLEMAN
The county also hosts Ironman 70.3 Eagleman on Sunday, June 8, in Cambridge.
This half-distance triathlon features a 1.2-mile swim in the Choptank River, a 56-mile bike course through the Blackwater National Wildlife Refuge and a 13.1mile run through Cambridge.
The event is ideal for both first-time triathletes and seasoned competitors with a flat course conducive to fast times and personal records. The swim takes place in the Choptank River, offering a calm and scenic setting.
The bike course is a singleloop route through the Blackwater National Wildlife Refuge, known for its natural beauty. The run course is a flat, scenic route through Cambridge, finishing at Gerry Boyle Park. Registration and information are available through the Ironman 70.3 Eagleman website.
Kent
COUNTY
Kent County: Exploring Eastern Shore hidden gems
From rolling hills to tiny tucked-away beaches, Kent County might be one of the Shore’s best-kept secrets. Nestled along the Chesapeake Bay, this charming county offers a rich blend of history, small-town charm, vibrant arts, and natural beauty that can be explored year-round.
As Capt. John Smith once wrote, “Heaven and earth never agreed better to frame a place for man’s habitation,” when he explored the Bay and its inlets, which he described as “fit for harbor and habitation.”
In 1608, Smith explored the Sassafras River, landing at a Tockwogh village near present-day Rock Hall. This area, so blessed by nature, would later become part of the land envisioned by Cecilius Calvert, the second Lord Baltimore, when he sent the ships Ark and Dove in 1634 to establish the colony of Maryland.
COLONIAL ROOTS
Kent County’s history stretches back to 1706 when the Maryland General Assembly pressed for the establishment of a “New Town” along the Chester River. This town, later known as Chestertown, became an epicenter for trade, with warehouses
and customs being established along the riverfront. As the first Maryland county to diversify its economy, Kent County transitioned from tobacco farming to grain cultivation, becoming a hub for merchants, shipbuilders and craftsmen.
Throughout the 18th century, Chestertown flourished as a colonial port town. Locally built ships were known for their sleekness and speed, ideal for sailing up and down the coast from New England to the Caribbean.
The town’s economy boomed, and its streets were lined with grand brick homes, many of which were owned by wealthy planters. The town was also a
it to Har est
^ Brampton Inn
center of culture, offering balls, horse races and theater performances for the social elite.
One of the county’s lasting legacies is Washington College, founded in 1782. The 10th oldest college in America, Washington College continues to play a vital role in the community today, with its historic campus serving as a landmark of education and culture.
THINGS YOU CAN’T MISS
Historic Chestertown: Stroll down its charming streets lined with historic buildings and enjoy local shops, cafés and museums.
Chestertown Tea Party: A local festival held every spring celebrating the town’s colonial roots with reenactments, parades and historical tours.
Rock Hall: Relax at the tranquil beaches of Rock Hall. The tiny town is called the Pearl of the Chesapeake for good reason. Known locally as Ferry Park, the small beach offers outstanding views of the Chesapeake Bay, the Bay Bridge and the western shore.
Mainstay Rock Hall: A cozy venue for live music and art, offering performances throughout the year.
BECOME AMEMBERTODAY &JOIN US FOR:
• Year ‘round social event s
• Highly qualified golf,sailing &swimming instruc tion
• Private boat launch and slips
• Best 18-hole golfcourseonthe EasternShore
• Driving range, pu tting green ¬ee times
• Bocce cour ts forcasual gatherings
• Reasonablypriced membership options Plus Your friends arealready here!
^ The popular Pirates & Wenches Weekend festival returns to Rock Hall in August.
Dickens of a Christmas: A festive holiday celebration in Chestertown that brings Victorian-era charm with a parade, horse-drawn carriage rides and shopping.
The Garfield Center for the Arts: Rife with history, the Prince Theater has been home to movie dreams from the advent of moving pictures to “talkies” before transforming to the intimate playhouse it is today with live performances by marvelous actors and actresses.
Kent County Farmers Market: Visit this year-round market in downtown Chestertown to enjoy fresh produce, local crafts and artisan products.
v The spirit of Christmas abounds in Chestertown. During the annual festival residents embody a Dickensian scene
ARTS, ENTERTAINMENT AND FESTIVALS
Kent County is rich in arts and culture, with a vibrant scene of galleries, theaters and music venues. Mainstay Rock Hall is a top spot for music lovers, offering performances by local and national artists throughout the year. This intimate venue features an art gallery that showcases local talent, offering a perfect evening out for art lovers.
Kent County’s festivals are a major draw for visitors. The Chestertown Tea Party Festival, held each May, commemorates the region’s colonial history with reenactments of the 1774 Tea Party, complete with period costumes, music and traditional foods. The event is a fun way to immerse yourself in Kent County’s historical atmosphere.
Another popular event is the Pirates and Wenches Fantasy Weekend in Rock Hall. This raucous event brings pirates, wenches and revelers from all over to partake in themed parades, costume contests and live entertainment. Whether you’re a fan of pirates or simply enjoy a good festival, it’s a can’tmiss event in Kent County.
Sultana Downrigging Festival is a premier event celebrating the region’s maritime history. Held each fall, it showcases majestic tall ships, offers educational programs and provides a stunning opportunity for photography and exploration. Visitors can tour these historic ships and learn about Kent County’s shipbuilding legacy.
The National Music Festival (June 1-14) is another must-see cultural event. Hosted at various venues throughout Kent County, this festival brings together world-class mentor musicians and gifted pre-professional apprentice musicians for two weeks of intense collaboration. Additionally, the festival records and broadcasts performances on National Public Radio, offering global access to Kent County’s vibrant arts scene.
NATURAL BEAUTY
Kent County is home to some of Maryland’s most pristine and tranquil outdoor spaces. Whether you’re into hiking, birdwatching or simply enjoying the beauty of the Bay, Kent County’s parks, beaches and nature preserves provide plenty of opportunities to get outdoors.
Eastern Neck National Wildlife Refuge is one of the county’s crown jewels, offering visitors a chance to explore a diverse ecosystem of tidal marshes, forests and wetlands. This refuge is ideal for birdwatching, with over 230 species of birds spotted throughout the year, including migratory waterfowl, songbirds and raptors. Visitors can explore the refuge through miles of trails, making it a perfect spot for nature enthusiasts looking to immerse themselves in Kent County’s wildlife.
Betterton Beach, for example, offers a peaceful escape with its clear waters and scenic views of the Chesapeake Bay. It’s an excellent spot for swimming, picnicking or simply taking in the sunset. Rock Hall’s Beach provides another great opportunity to enjoy the Bay, with quiet stretches of sand perfect for a peaceful day by the water.
Kent County is a treasure trove of history, culture and natural beauty. From its colonial roots and maritime heritage to its thriving arts scene and outdoor adventures, this hidden gem on the Eastern Shore offers something for everyone. Whether you’re visiting for the weekend or planning a longer stay, Kent County is sure to leave you with lasting memories.
For more information on events and activities in Kent County, visit Kent County Tourism or the Kent Chamber of Commerce.
This article was compiled from Kent County Tourism information and the Kent County News archives with the assistance of ChatGPT. The story was subsequently edited and fact-checked by Hannah Combs.
Talbot County Chamber of Commerce with the
Alpine Lakes & Scenic Trains
Trip Dates: May 3-13, 2026
Explore the stunning landscapes of Switzerland and Northern Italy aboard legendary Alpine trains Glacier Express and Bernina Pass Train.
Visit resort towns Zermatt, St. Moritz, and Lake Maggiore, and ascend Mount Pilatus for breathtaking views.
Chamber membership not required to take advantage of our exclusive group pricing.
Scan QR code to learn more and reserve your spot.
SHOOT SHOOT FOR FOR SUCCESS SUCCESS
Event Date: October 3, 2025 | Pintail Point
Join us for a day of fun and friendly competition at our annual Shoot for Success Sporting Clays Tournament! Proceeds benefit the Chamber’s Small Business Resource Center, helping local entrepreneurs grow and thrive. Perfect for any experience level.
Sponsorships and team registration now open scan the QR code to learn more and reserve your spot.
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