Easton – the Hamptons of the Chesapeake Bay

Affluent meets working-man in Easton and they make it work. Cabelas folks and Orvis peeps live in the same town for the same reason: the outdoor life – boating, hunting, fishing and biking (both motor and cycling).

Easton is close to, but not on, the Chesapeake Bay. The inland town is on the edge of a maze of tributaries that flow into the bay with more than 600 miles of shoreline. That makes rich farmland, major marshland hunting and an unusually large number of waterfront mansions.

The town was founded in 1710 and became a tobacco growing area. Colonial merchants and Victorian businessmen built large homes over the years encircling the downtown area with a range architectural styles.

Because of the unusual combination of wealth and rural, Easton is known for wildlife and nature art, fine dining, shopping, and its music scene. Nationally-know performers often stop by Easton.

In 2020, Kiplinger magazine ranked Easton #8 in the number of millionaires as a percentage of the total population.

Forbes Magazine declared Easton one of “America’s Top 5 Coolest Towns to Buy a Vacation Home” in 2021. They said it has a level of celebrity discretion on part with the Hamptons, as well as year-round culture and “a farm-to-table foodie scene that gets better every year.”

Easton’s Historic Business District

Downtown Easton

The business district is rectangle of streets in front of — instead of surrounding — the Talbot (pronounced “TALL-butt”) County Courthouse (11 North Washington Street).  Each street is lined with historic buildings.

North Washington Street runs in front of the courthouse and features offices and businesses related to the local government, including some eateries.

Goldsborough Street is the home to several art galleries, artistic crafts, home furnishings and interior design.

Harrison Street goes in front of the historic Tidewater Inn (101 East Dover Street), worth a walk-through if you’re strolling about.

Historic Tidewater Inn

Boutiques and consignment shops have gathered across the street from the inn.

Easton Boutiques

The shops typically offer both high-end and modest priced items.

Dover Street is an antique row with a gunsmith shop tucked among the antique stores.

On the first Saturday of each month, art galleries stay open extended hours for what’s called First Saturday Gallery Walk. Be aware that many of the businesses are closed on Sunday.

The Easton Welcome Center (11 South Harrison Street) is also closed on Sunday, but they’ll leave brochures and tour maps in a basket hanging on the door.

The historic district has a number of handy kiosks with maps showing where you are and listing where you might want to go. The Welcome Center also has a public parking lot.

Walking tour information can also be downloaded.

Historical Society of Talbot County (25 South Washington Street) is behind the Welcome Center. The Society is in a 1805 Federal-style Quaker townhouse in what they call a campus.

It includes several historic houses and a beautiful English-style garden maintained by the Talbot County Garden Club. The Society offers tours of historic Easton, as well as it’s small “campus” which includes a cabinet-maker’s shop, a Federal-era home and gardens.

On the corner of Harrison & Dover is the Avalon Theatre (40 East Dover Street), a former 1920s movie house, now a performing arts center. It shows New York’s Metropolitan Opera live on screen as well as notable national musicians, film screenings and dramatic theater.

Avalon Theatre

The historic residential area starts a block in any direction away from the business district with a wide range of beautifully maintained homes ranging from Colonial and Federal to Victorians and American Craftsman, with some Antebellum mixed in. Well worth a walk-about on a nice day.

Easton’s Incredible Art Museum

Easton Museum
Academy Art Museum

The Academy Art Museum (106 South Street) is in the residential area. It’s a strange combination of building styles, started in 1820 as a school and added onto as the type of school changed over the years. It was the county’s first public high school and became a museum in 1960.

The first floor contains rotating exhibits, which often include major works from national and regional museums. Check the website for the current exhibit. The rest of the museum contains classes and lecture/concert halls. There is a small fee to visit the exhibits.

“The Hill,” Historic Neighborhood of Freed Slaves

The Hill, an Easton neighborhood started by freed slaves

Two blocks from the museum is an area worth visiting called The Hill, believed to be formed in 1790 by former slaves freed by Quakers and abolitionists.

An estimated 400 freed blacks lived in the Easton area during that time. Walk to Aurora Street to find wonderfully maintained historic brick and wood-frame homes, many with unique short, but wide, front porches.

Archeologists from the University of Maryland and Morgan State University have been digging in the neighborhood and some believe, that based on what they’ve found so far, The Hill may give New Orleans’s Treme neighborhood competition as the oldest African-American community in the U.S.

Easton, Religious Haven for Quakers

In Colonial days, Maryland was known for being a religious haven for Quakers and Catholics. Third Haven Friends Meeting House (405 South Washington Street), outside the historic district on South Washington Street, is the oldest surviving meeting house of the Religious Society of Friends, known as Quakers. It was built in 1684 is still used for worship on Sunday mornings and Wednesday evenings.

Inside the original meeting house in Easton. The panels in the back wall can be raised or lowered to separate the two ends of the church.

The original meeting house is open to visitors. You can see the original Colonial wooden construction that has never been updated (repaired, but not updated).

Nearby is a brick meeting house, built in 1880. It’s used in winter months since the original is not insulated. That building is not open to visitors outside of meeting times. A walk through the cemetery is a walk through time.

Cycling in Easton

Easton Railroad station, now a bike route
Pennsylvania Railroad station in Easton

Easton has a bike trail that runs through the historic district. The Easton Rails-to-Trails runs about 2.5 miles from Dutchmans Lane (in southern Easton) to North Easton Park. Some of the neighborhoods it goes through might seem a bit sketchy, but it’s a nice, short ride.

Along the trail at the Goldsborough Street crossing, there’s the Pennsylvania Railroad Station, built in 1904. It’s now a visitors center and museum run by the Easton Historical Society, specializing in the history of all things local.

Easton is actually a central starting point for many Talbot County cycling routes on the wide shoulders of the state’s highways. The country tourism bureau has put together maps showing the different routes near the Chesapeake Bay, through farmland, along historic routes and even one highlighting Maryland’s “state sport” of jousting.

Easton is Home of Frederick Douglass

Former slave, author and politician Frederick Douglass was raised outside of Easton. His statue stands on the courthouse lawn in Easton. And, there are signs to historical points marking his life, but there’s controversy over the accuracy of those locations. Also, the signs are hard to follow. 

The Historical Society of Talbot County has created a driving tour map that shows the areas where the civic leader once lived.

Festivals in Easton

Easton Waterfowl Festival

On summer weekends, live music can be heard on the streets in various locations. And throughout the year, the town hosts at least one festival a month.

Easton is best known for its Waterfowl Festival. Schools shut down to make room for the three-day event over the second weekend in November.

Every available public space is used for wildlife art shows, hunting and fishing competitions, and duck decoys. Duck decoys can range from $20 to $10,000, depending on the art quality.

People come from across the country for the goose and duck calling competitions. These are sanctioned events and winners in Easton are considered national champions.

The festival is big; shuttles take you around town. You can’t see the entire festival in one day. 

Here’s a list of other festivals. 

Easton Farmers’ Market

Easton Farmers Market
Easton Farmers Market

Easton Farmers’ Market (325 Northampton Street) is open year round with about 40 vendors.  It claims to be the oldest continuous open-air farmers’ market in the U.S., selling local produce and crafts since 1752. The market is open only on Saturdays. The hours vary depending on the season.

The town also has a large Amish market, called The Amish Country Farmers Market (101 Marlboro Avenue). It’s open Thursday through Saturday.

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