Kent County, Maryland Tourism

11/03/2026

🚂🌾✈️ TOURISM TUESDAY: Discovering Massey, Maryland! 🌾🚂✈️

📍 Kent County, Maryland — Where Small Towns Have BIG Stories!

Did you know that the quiet little community of Massey, Maryland, was once a bustling railroad hub filled with hotels, stores, travelers, and farmers shipping their crops to market? 🚂

Today, Massey may be known for its peaceful countryside, but its history tells a fascinating story of growth, transportation, and Eastern Shore agriculture!

🏡 FROM MASSEY'S CROSSROADS TO A RAILROAD TOWN

Originally known as "Massey's Crossroads", this small community in northeastern Kent County, near the Delaware state line, was named for the Massey family, whose roots in the area date back to the late 1600s.

Located at the intersection of roads connecting Millington, Sassafras, Galena, and Delaware, Massey became a natural gathering place for farmers, merchants, and travelers.

🚂 WHEN THE RAILROAD PUT MASSEY ON THE MAP!

The 1870s brought big changes to this little village!

In April 1870, the Kent County Railroad began operating between Massey and Kennedyville. By February 1872, the railroad had reached Chestertown!

Massey became an important railroad junction, connecting communities throughout Kent County with Delaware and larger markets.

🍑 Here's a fun fact! Massey was once part of a thriving peach-growing region! Farmers relied on the railroad to transport fresh peaches and other agricultural products to markets far beyond Kent County.

And just how busy was Massey?

An account from April 1872 described the village as having:

🏨 TWO large hotels!
🏪 THREE stores!
🏡 Several newly constructed homes!

Not bad for a little country crossroads!

By 1895, Massey had an estimated population of only 120 people, but it still maintained a railroad station, post office, express office, and businesses supporting the surrounding farming community.

🌾 MASSEY TODAY — COUNTRY CHARM & EASTERN SHORE ROOTS

Fast-forward more than 150 years, and Massey looks quite different!

The bustling railroad activity has faded, but the community has held on to what makes Kent County so special — beautiful farmland, quiet country roads, historic buildings, and a strong agricultural heritage.

You won't find a bustling downtown filled with shops and restaurants, but you WILL find some wonderful hidden treasures!

✈️ MASSEY AERODROME & AIR MUSEUM

One of Massey's most unique attractions is the Massey Aerodrome, located at 33541 Maryland Line Road!

This fascinating aviation museum features vintage airplanes, historic aircraft engines, restoration projects, and aviation memorabilia.

Visitors can experience a piece of aviation history at an operating grass airfield! The museum also hosts special aviation events and fly-ins.

⛪ ST. CLEMENT'S EPISCOPAL CHURCH

With roots dating back to 1855, this historic church is another reminder of the generations of families who helped shape the Massey community.

❤️ SMALL TOWN, BIG HISTORY!

It's amazing to think that a place so peaceful today was once alive with steam locomotives, railroad passengers, busy merchants, and farmers loading peaches and grain for shipment!

Massey is a perfect example of how Kent County's smallest communities played important roles in shaping the history of Maryland's Eastern Shore.

And while the trains may no longer bring the same hustle and bustle, Massey's beautiful countryside and rich heritage continue to tell a story worth sharing.

10/31/2026

🎃👻 HAPPY HALLOWEEN FROM KENT COUNTY, MARYLAND! 🧡🖤

There’s something a little spooktacular about Halloween on Maryland’s Eastern Shore! 🍂

From the historic streets of Chestertown to the waterfront charm of Rock Hall, and all our wonderful small towns in between, Kent County is full of fall beauty, Halloween spirit, and maybe even a ghost story or two! 👻🏚️

🍁 Colorful leaves and crisp autumn air
🎃 Pumpkins, costumes, and spooky decorations
🍬 Trick-or-treating and family traditions
🦇 Historic towns with centuries of stories to tell

Whether you're heading out with the little ghosts and goblins, enjoying a Halloween party, or staying home to hand out candy, we hope your Halloween is filled with laughter, sweet treats, and just the right amount of fright!

🧡 **From our little corner of the Eastern Shore, we wish everyone a safe, fun, and

10/30/2026

🏡📜 FUN FACT FRIDAY! 📜🏡

🌊 Did You Know? Turner’s Creek Has Over 350 Years of History!

Travel back to 1675, when Edward Blay was granted 200 acres of land along Turner’s Creek, near present-day Kennedyville in Kent County, Maryland! The property was known as “Blay’s Range.”

⚓ Back in colonial times, waterways were the highways of the Eastern Shore! Turner’s Creek provided access to the Sassafras River and Chesapeake Bay, making it an ideal location for shipping to***co, grain, timber, and other goods.

Over the years, Turner’s Creek developed into a bustling waterfront trading area, complete with a wharf, shipyard, tannery, and granary!

🌽 During the Revolutionary War era, the landing became an important part of the region’s agricultural shipping history. Local tradition even connects grain shipped from Turner’s Creek with supplies for American troops!

⛪ Edward Blay also left his mark on the community. In 1709, he donated two acres of land for Shrewsbury Church, helping establish a landmark that remains part of Kent County’s history today.

🪶 But here's something even more fascinating! Long before European settlers arrived, the Tockwogh Native Americans inhabited the Sassafras River region. Captain John Smith encountered their community during his explorations in 1608!

📍 Today, Turner’s Creek Landing remains a beautiful reminder of Kent County’s colonial past and its deep connection to the Chesapeake Bay.

❤️ Next time you're exploring the Kennedyville area, remember that these quiet country roads and waterways were once part of a thriving colonial landscape!

💬 Have you ever visited Turner’s Creek Landing or heard stories about its history? Share them below!

To view land records from 1658-1867: https://www.georgesbasement.com/LangfordOnMassey/MasseyDataBank/MasseyLandRecordsKentCountyMaryland.htm

10/28/2026

🔔🎄MARK YOUR HOLIDAY CALENDARS🎄🔔

Main Street Chestertown's signature holiday event, Dickens Of A Christmas - Chestertown, MD , returns Friday, Dec. 4, and Saturday, Dec. 5, 2026, transforming historic downtown Chestertown into a holiday scene straight out of 1840s Victorian England. Visitors can expect live music, street performers, local and visiting artisans, bonfires, brews, an outdoor Victorian living room, carriage rides, and the annual seasonal cheer that will make even the stodgiest Scrooge merry.

Expect the fan favorite holiday home tour, downtown streets filled with locals donning their best Victorian outfits, and two shows from North America’s favorite Celtic band, The Devil’s Brigade. Main Street Chestertown is putting local merchants front and center with Dickens Destinations, a new initiative bringing curated Victorian experiences directly to downtown storefronts. Visitors can sip Victorian hot chocolate outside Bespoke Chocolate, enjoy Dickensian cocktails at Modern Stone Age, browse an open-air book market at The Bookplate, snap a portrait in Yarrow & Wren’s porch, or sit for a palm reading in Bee Crafty Collectibles’ window. Additional features include Fezziwig’s Fortune Wheel spins, tarot readings by Rissa Miller, and a Chestertown RiverArts craft station inside the Heritage Village in The Bank.

For more details, please visit: www.mainstreetchestertown.org/dickens-festival/.

10/28/2026

Congratulations to The Little Lemon Leaf Diner !

10/27/2026

Visit Chestertown this holiday season and step into a Victorian Christmas! 🎩🌟 Dickens Of A Christmas - Chestertown, MD brings history, charm, and holiday spirit to life. See you there!

10/27/2026

🌾 TOURISM TUESDAY: CHESTERVILLE, MARYLAND 🌾

You may have driven through Chesterville a hundred times…but did you know how much history is hiding at this little Kent County crossroads? 👀

📍 Located around the intersection of Routes 290 and 447, Chesterville has roots stretching back to the 1700s. The area was once known as New Market and grew into a busy little rural village serving the surrounding farms.

By the late 1800s, Chesterville had general stores, churches, schools, a hotel, post office, physician, blacksmiths, wheelwrights, carpenters and even a shoemaker! 🐴🔨📬

🏠 One of the area's historic treasures is the Chesterville Brick House, believed to date to shortly after 1773 and now listed on the National Register of Historic Places.

Chesterville is also part of Kent County's important African American history. Following the Civil War, African American families established homes and a community along Chesterville Forest Road. Asbury United Methodist Church at Chesterville Forest became an important center for worship and community life, and Chesterville was also among the Kent County communities where schools for African American children were established during the years following emancipation.

🌳 CHESTERVILLE TODAY

Today, Chesterville is much quieter than the bustling little crossroads village it once was—and that's part of its charm.

You'll find beautiful farmland, country roads, historic homes, open spaces and that peaceful Eastern Shore way of life. It's a place where Kent County's agricultural roots are still very much visible.

Chesterville may be small, but its history tells a BIG story about how the rural communities of Kent County grew and changed over the last 250+ years. ❤️

Sometimes the places we drive through every day have the best stories!

10/23/2026

🦟🏛️ FUN FACT FRIDAY: WHEN CHESTERTOWN CLOSED ITS DOORS — 1793

Did you know Chestertown may have been one of the first towns in America to take official action against the deadly Philadelphia Yellow Fever Epidemic of 1793?

In the summer of 1793, yellow fever swept through Philadelphia, then the nation's capital. Nearly 5,000 people died, and thousands fled the city.

That created a frightening situation for Chestertown. A regular stage route connected Philadelphia to Maryland's Eastern Shore, bringing travelers directly toward town.

🚨 On September 10, 1793, Chestertown took action.

Residents held a meeting, formed a Committee of Health and Inspection, restricted stagecoach traffic through town, and established a place outside Chestertown where sick or suspected travelers could be isolated and cared for by a physician.

Contemporary writer Mathew Carey later wrote:

“The first public act that took place on the subject, as far as I can learn, was at Chestertown, in Maryland.”

Even more interesting—Chestertown acted before similar measures were announced in New York.

⚔️ You may have heard that Chestertown was placed under “martial law” during the epidemic. While the town clearly took drastic steps to restrict travelers, contemporary records I've found describe a public-health quarantine rather than an official declaration of martial law.

And here's the irony: people in 1793 didn't yet know that yellow fever was spread by infected mosquitoes, not simply by being near a sick traveler.

More than 230 years ago, Chestertown residents were already organizing to protect their community during a public-health crisis.

📍 Chestertown, Maryland | September 1793

Just another incredible chapter of history right here in Kent County. ❤️

10/22/2026

Your perfect escape begins in Kent County!

Where historic inns whisper stories of the past, bed & breakfasts welcome you with comfort, and marina stays offer front‑row views of the Chesapeake Bay. Come for the charm, stay for the moments you'll never forget.

Start your journey at: www.kentcounty.com/visitors/places_to_stay.

Kent County's waterfront towns of Chestertown, Rock Hall, Galena, Betterton, and Millington offer outdoor recreation, local seafood, and Maryland’s second largest collection of 18th century structures and so much more. Visit www.kentcounty.com