WHY GO: Some of the most inspiring things to do in Easton MD in Talbot County revolve around Frederick Douglass, who was born and enslaved here – later returning a hero in his older age.
Situated on Eastern Shore of Chesapeake Bay, Easton and the surrounding area has been a farming region ever since Europeans first settled here. Plantation owners became wealthy on the backs of enslaved people – like Douglass, who was six years old when first “rented out” to one such landowner.
Yes, follow in the footsteps of Frederick Douglass. But, also join a ghost tour, stop into an art museum and art galleries, visit an historic grist mill, sip wines at a vineyard, and eat at great restaurants in a surging downtown.
Recent high-end downtown growth, in fact, can be attributed to one person: New York energy mogul, Paul Prager, who has turned Easton MD into a foodie destination. Prager, a graduate and board member of the US Naval Academy in Annapolis, has obvious long-term ties to the Chesapeake region.
So, if African American History, and swanky new Eastern Shore shops and eateries make the two of you weak in the knees, Easton is the romantic getaway for you.
Herewith, we recommend the most intriguing and effecting things to do in Easton Maryland for a two or three day escape.
Easton MD is on our list of 17 Best Romantic Getaways in Maryland. Check it out for more adventures with your loved one.
Things to Do in Easton MD and Surrounding Area
TOURS: Trace the Footsteps of Frederick Douglas on Four Driving/Walking Tours
Black abolitionist and celebrity speaker, Frederick Douglass was born into the Bailey Family (he changed his name to F. Douglass after escaping bondage to avoid capture) and spent his childhood years enslaved in Talbot County MD.
Four driving and walking tours were created to follow his whereabouts during this time. Click link for online tour – or go to the Talbot County Visitor’s Center in Easton to pick up a hard-copy brochure.
Tour #1 From Easton – F.D. From Baby To Teenager
You’ll drive 12 miles from the Talbot County Courthouse in Easton (photo op of the statue of Douglass that stands outside the front door) to Covey’s Landing. It’s a lovely ride past farmland and river – a landscape that really hasn’t changed much since 1818 when Frederick was born on the banks of the Tuckahoe River.
A transportation artery, the Tuckahoe was also where the Baileys and other enslaved people got information about the wider world. The tour guide directs you to look across the field at Tapper’s Corner to where Douglass was born (no buildings remain).
Be sure to stop at the new 107-acre Frederick Douglass Park – which has interpretive signs and a walkway that overlooks the river. Virtually unchanged for hundreds of years, this was the landscape Douglass grew up in.
The final stop, Hillsboro Landing (in Caroline County) coincides with the Maryland Civil War Trail. Frederick’s grandmother sold fish from the river in town. You can launch a canoe or kayak from a boat ramp here, and, while floating along, imagine Douglass as a young child fishing and learning about the world here.
Tour #2 From Easton: Enslaved Teen Bailey (Douglass) Lent To Lloyd Plantation
Drive the 13 miles from Easton to Wye Town Farm, and imagine a six year old Frederick walking with his grandmother for hours past these dense woods and farms. He was summoned by and stayed with Aaron Anthony, the “Overseer of Overseers” at the 20-farm strong Lloyd Plantation.
A conglomerate of the day, the Lloyds enslaved thousands of souls to work their twenty farms. Douglass lived on Edward Lloyd V’s land from 1824-1826. You’ll pass by much of this property on this driving tour – plus get a peak at still private plantation homes (just don’t turn in to gated driveways). The tour also takes you to cemeteries – one where both free Blacks and Black Union Soldiers are buried.
Tour #4 – Easton Walking Tour
This walking tour intersects with The Hill Community (see below) and begins at the Public Landing at Easton Point. Between 1819 and 1847, Baltimore slave traders sold enslaved people south from here. However – it was also where a free Frederick Douglas returned from Baltimore as a US Marshal in 1878.
Next, stop at 100 Port Street, where the Easton Colored School stood. This is where, in 1893, Douglass addressed the assembled children recounting the story of “a boy who lost his parents, was once a slave forced to sleep on a cold floor, but who taught himself how to read and speak, hold high public offices, and accumulate some wealth. That boy was Frederick Douglass, and what is possible for me is possible for you.”
Other stops in Easton include the site of the jail where 18 year old Douglass was held for a week for “the offense of intending to run away from slavery.”
There are further stops at the Asbury United Methodist Church (still standing), which Douglass dedicated on his 1878 return tour; the Bethel A.M.E. Church – the oldest AME congregation on the Eastern Shore, established in 1818; and the Tidewater Inn, where Douglass stayed over in 1893, when it was the Hotel Avon.
TOUR: The Hill – New Rosato Mural
Home to free African Americans since the 1790’s, the Hill neighborhood in Easton MD was diverse decades before the Civil War (although, oddly it became segregated afterwards). There were more free African Americans living in Easton, working as merchants, midwifes, sailors, craftsmen, and preachers, than anywhere between Florida and New York.
A new Frederick Douglass Mural, by Michael Rosato, depicts the charismatic and scholarly abolitionist and his wife – set against a backdrop of African Americans as teachers, soldiers, politicians, historians, and in other professions.
You’ll also stand before a couple of churches of historical significance. One, the Bethel A.M.E Church, founded in 1818 – the year Frederick Douglass was born. The other the Asbury United Methodist Church, dedicated by Douglass on his 1878 tour of Easton.
VISIT: Academy Art Museum, Easton
Though small, the Academy Art Museum is a vital community institution, with exhibits ranging from Art Academy member’s work to world-renowned artists’ shows. Considered a Regional Art Museum, the Academy is “dedicated to bringing great art to the Eastern Shore.”
It also brings a lecture series, dance classes, concerts, workshops demonstrations and special events to its sunlit galleries and grounds.
GO: Avalon Theater, Easton
The small town art deco Avalon Theatre showcases some mighty big performing acts, from Second City Improv to top musicians and bands. The theater also sponsors Plein Air Easton, the largest and most prestigious outdoor painting competition in the United States.
GHOST TOUR: Easton Ghost Tour with Chesapeake Ghost Tours, Easton
From the Chesapeake Ghost Tours webpage: “Enjoy a guided night walk through the Town of Easton, historically the “Eastern” capital of Maryland. Hear about the spirit of Marguerite, the murdered actress found in the elevator of the Avalon Theater.
Learn about Mr. Grymes who is still demanding fine service of the staff at the Tidewater Inn. Meet “The Colonel” who haunts the courthouse and the phantom man in a blue suit who rides the elevator in the old jail.
Hear how the spirit in the old Odd Fellows hall has “touched” the staff at the Clay Bakers. Visit the Home of the Friendless, the Eastern Shore’s oldest orphanage and listen for sound of Solomon Barrett playing his fife and drum in the old cemetery that also has two “healing trees.”
The scariest stop of all will be at Foxley Hall, the most haunted house in Easton where mist and fog frequently appear inside the kitchen and living area, and where the screams of a woman are sometimes heard from a 3rd floor room. You’ll learn much about Easton’s history and more about the spirits that still hang around.” Check website for times.
VISIT: Wye Grist Mill, Wye Mills
Originally built in 1682, the modest, still working Wye Grist Mill supplied ground wheat to George Washington’s troops at Valley Forge. It’s considered the oldest water-powered gristmill in the U.S.A.
The lower level is a “Museum of Wheat” depicting history of the grain in the area (now mostly planted with Soy and Corn, used as feed for the poultry industry), and upper level where you can watch a milling demonstration and purchase bags of flour, buckwheat, cornmeal and other ground products, right from the source. Open Mid May to Mid Nov.
VISIT/TOUR/FUN: Councell Farms, Cordova
With the threat of being crowded out by Big Agri-Business, family farms must innovate to stay solvent. Some have turned into wineries or breweries, others to growing specific “artisan” produce. Councell Farms did something else entirely. It’s got the most engaging, exuberant human-powered playground you’ll ever see in a fallow field.
For a modest fee, your kids (and/or your “inner child”) can climb up to sit in the cab of a decommissioned combine then slide back down through a plastic tube, pedal tricycle go-carts, pump water the old fashioned way, jump on a massive bounce-ball, shoot scarecrows with slingshots, race plastic ducks, wind your way through a straw or corn maze, and plenty more.
When exhausted, have an ice-cream cone from the on-site creamery and then buy some just-picked produce or autumnal decorations to take home.
VISIT: Triple Creek Winery, Cordova
Three brothers, Paul, Alex and Corey Spies, opened Triple Creek Winery on their farm because “our family is very social.” Twenty five years ago the Spies planted vines on their property for other winemakers in the area, with more added six years ago.
As many visitors who drop in are “new to wine,” Triple Creek focuses on the type of vintages that suit them; Blackberry Rose being the biggest seller.
To increase sales, the Spies also started growing English Cucumbers in hothouses on the farm. They now ship 1,600 cases of the plastic-wrapped tea-sandwich veggie to Whole Foods in Baltimore and DC per week. Check website for concerts and events.
Restaurants In Easton MD
EAT: The Ivy
The Ivy is everyone’s favorite pick-up spot for soups, salads, and sandwiches. I can vouch for their delectable freshness.
EAT: Locals Recommend
Out of the Fire for wine and casual bites in a elegant café setting, Legal Assets for Asian Fusion, Headwaters Seafood & Grille for fresh bayfood, Bas Rouge for refined modern European, and Doc’s Downtown for traditional Eastern Shore fare.
Hotels in Easton MD
STAY: Tidewater Inn, Easton
The Tidewater Inn is the granddaddy of inns in Easton – smack in the center of town. A curved staircase was all that was left of the place when the original burned to the ground in 1944. The graceful stairway has been incorporated in the lobby of this distinguished brick hotel, rebuilt and reopened in 1949.
Rooms and suites were updated in 2016, with clean-lined traditional décor (lots of grey – no floral chintz), new stunning bathrooms and modern amenities. .