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The “Capital of the Eastern Shore,” Easton, Maryland offers a charming blend of history, culture, and outdoor activities, making it a diverse travel destination. Its historic downtown, centered around North Washington Street and the Talbot County Courthouse, features beautifully preserved 18th and 19th-century architecture, art galleries, unique boutiques, and fine dining.

Additionally, Easton enjoys a thriving cultural scene. You can catch a live performance explore a variety of art exhibitions, and attend numerous cultural festivals and events throughout the year, celebrating music, arts, and local culture.

Street scene in downtown Easton, MD

**Disclaimer: This was a hosted stay, however, all opinions are my own. I strive to provide my readers with my most authentic sentiments.

With over 600 miles of tidal shoreline, Talbot County, where Easton is located, offers water-related things to do like sailing, sportfishing, kayaking, and paddleboarding. Visitors should also take time to learn about the region’s maritime history and the connection its people have had with the bay.

Finally, Easton makes the perfect hub for visitors to the Eastern Shore of Maryland who want to explore quaint smaller towns throughout the region. And there are plenty of hamlets and hideaways to explore if you know where to look.

Visit the Historic Talbot County Courthouse

An iconic symbol of Easton and the county, The Talbot County Courthouse was constructed in 1794 and is one of Easton’s oldest buildings. Constructed in a Georgian architectural style, characterized by its symmetrical design, red-brick construction, and white pillars it is set among mature trees in the heart of Easton’s historic district. 

Frederick Douglas statue outside the Talbot County Courthouse in Easton, MD
Image courtesy of the Chesapeake Bay Program, CC License

Easton has a rich African-American heritage. The renowned abolitionist and former slave, Frederick Douglass, was born in Talbot County and was imprisoned in this courthouse after attempting to escape slavery in 1836. Today a statue of Douglass stands in front of the courthouse where he delivered his “Self-Made Men” speech in 1878.

For those interested in the life of Frederick Douglas and his time in Talbot County there are four, one-hour driving tours covering his birth near the Tuckahoe Creek up to and including his 1878 and 1893 returns to Talbot County.

Take a Historic Easton Walking Tour

Immerse yourself in Easton’s legendary history with a tour conducted by the Talbot Historical Society (30 S. Washington Street). These tours, led by knowledgeable guides explore Easton’s historic downtown district, and its well-preserved architectural treasures, as well as provide a glimpse into the town’s storied past.  Our guide regaled us with accounts of the town’s role in regional and national history creating a tour that was both informative and engaging.

Tour guide in Easton MD

But tours are not the Talbot Historical Society’s primary function. The society maintains extensive collections of historical artifacts, historical documents, photographs, and records related to Talbot County’s past. Whether you’re a researcher, historian, or simply someone interested in learning more about local history, the society offers valuable resources and educational opportunities to help you connect with the region’s past.

Garden enthusiasts will want to visit the Talbot Historical Society’s award-winning gardens. Occupying one acre between Hill Research Center and the Neall House Galleries, the gardens are a partnership with Talbot County Garden Club and feature mature boxwood, a terraced shade garden, an herb garden, well-established perennial beds, and flowering trees.

Hydrangeas in a garden outside the Talbot Historical Society in Easton MD

Enjoy the Arts

Patrons of the arts can catch a live performance at the historic Avalon Theatre a popular music venue that hosts performers in a range of genres. The Ebenezer Theater, part of the Prager Family Center for the Arts, offers an intimate setting for audiences to enjoy world-class performances. 

Easton is home to many art museums and galleries including the Troika Gallery (9 S Harrison St), the oldest and largest, fine art gallery on the Eastern Shore. Pay a visit to the Academy Art Museum which features a variety of art exhibitions and offers numerous artist-led workshops.

Brick exterior of the Prager Family Center for the Arts in Easton, MD

Indulge in Easton’s Food Scene

If you are looking for someplace approachable with stellar food in a delightful atmosphere, try Out of the Fire. Situated on the edge of Easton’s historic district, at 111 South Washington Street, this restaurant not only offers inspired farm-to-table meals, including gluten-free and vegetarian options, but also food you can feel good about.

Restaurateur Amy Haines and her crew live by the motto, “Eat Well, Be Well, Give Back.” This is achieved by partnering with local growers, using sustainable practices, and lending support to the community, especially local artists who display their works on the walls. Much of the artwork you see at Out of the Fire is available for purchase. 

Delicious peach dessert from Out of the Fire in Easton MD

In recent years, the introduction of several downtown establishments from Bluepoint Hospitality Group has elevated Easton’s culinary scene. For a special night out, try Bas Rouge, which serves contemporary adaptations of European classics with time-honored fine dining, or The Wardroom, a distinctive culinary shop, wine shop, and bistro serving Italian classics.

Attend a Festival

Easton hosts numerous festivals and events throughout the year, celebrating music, arts, and local culture, including the Chesapeake Music Festival; First Friday Art Walk; Fire & Ice Festival; Chesapeake Film Festival; Plein Air Easton; Old Tyme Fourth of July, and more.

Duck Decoys
Image by, Chesapeake Bay Program, CC License

Every November visitors flood the streets of downtown Easton for the annual Waterfowl Festival, a three-day celebration of wildlife and nature, local heritage, food, and fun. The festival features wildlife art, retriever demonstrations, Dock Dogs competitions, goose and duck calling contests, and stre­et musicians. It is the perfect place to start your holiday shopping. You will find unique items for everyone on your list from a variety of vendors. Support local organizations while sampling mouth-watering Eastern Shore cuisine.

Easton Amish Market

Dating back to the 1980s, the Easton Amish Market (101 Marlboro Avenue, Easton) offers a delightful blend of Amish delicacies, artisan crafts, handcrafted furniture, home decor, and unique gifts. Local businesses and Amish vendors showcase meats, farm fresh produce, cheeses, salads, soups, pastries, soft pretzels, candies, and ready-made meals. An Easton staple, this market, open three days a week offers locals and visitors a taste of Easton and an authentic Eastern Shore experience. 

No trip to the Easton Amish Market would be complete without a visit to the Old Tyme Candy Shoppe. This throwback to days gone by carries your favorite sweet treats from childhood as well as candy apples, Jelly Belly Jelly Beans, Asher’s Chocolate, fudge, and more. 

Loaves of fresh baked bread in baskests for sale at market
Image by, Chesapeake Bay Program, CC License

The Easton Amish Market should not be confused with the Easton Farmers Market, an outdoor market held in Scott Park, every Saturday from 9 a.m. to 1 p.m. between May and December. From mid-January through the end of April, this market moves to the 300 Block of Northampton Street in front of the Easton Public Market. Winter hours are 10 am to 12 noon.

Bike Maryland’s Eastern Shore

The flat terrain of Maryland’s Eastern Shore makes it a great destination for cycling enthusiasts. Explore the area’s scenic beauty by renting a bike or bringing your own. Bikes can be rented from Easton Cycle and Sport, Shore Pedal & Paddle, and Tilghman Island Marina. In addition to rentals, these local outfitters are also there for you in the event of mechanical issues.

One popular and picturesque loop takes you from Easton to Saint Michael’s, through Royal Oak, and crosses the Tred Avon River on the Oxford-Bellevue Ferry before looping through Oxford and returning to Easton. This 33-mile loop is entirely on flat paved roads. While most of the route is on rural roads, you will encounter some heavily trafficked areas, especially in the towns of Easton and St. Michaels.  

Coastal scene on a gloomy day in St. Michael MD

Not feeling quite that ambitious? Then perhaps a casual ride on Easton’s Rails-to-Trails is more your speed. This quick 2-½ mile out and back, paved path is great for families and recreational riders. 

From south to north, the trail runs from Dutchman’s Lane and terminates at North Easton Park taking riders directly through historic Easton. In addition to being a wonderful recreational path, it is also handy for quick jaunts to the store. Parking is available at Idlewild Park on the southern terminus and North Easton Park on the north end. Public restrooms are available at North Easton Park.

Oystermen getting ready to bring in the days catch at the dock in Bellevue MD

If you enjoy rail trails, then you may also consider the 1.3-mile St. Michaels Nature Trail. Where the Easton trail is an in-town trail, this asphalt path runs along the western edge of St. Michaels through natural areas, past a horse farm, and across a covered bridge offering a scenic ride.

Parking is available on the trails southend off S. Talbot Street. On the northern end, parking is located at the lot for Bradley Park on Railroad Avenue. There are no public restrooms or water fountains on this stretch of trail. 

Stay at a Historic Inn in Downtown Easton

Plan a stay at the Tidewater Inn. This newly updated luxury hotel offers all the modern conveniences while retaining its historic charm making it the perfect fusion of old and new. It is a fantastic place to use as your home base during your Eastern Shore getaway. This beautifully appointed inn located in the center of town gives you easy access to all that Easton and the Eastern Shore have to offer. 

A guest suite at the Historic Tidewater Inn in Easton MD

If you are planning a large family gathering or need accommodations for your wedding party then consider the Tidewater House. This elegant historic mansion built in 1874, located at 202 Dover is part of the Tidewater family of properties. This means you have access to the amenities and services at the inn including Terrasse Spa and Hunters’ Tavern. 

Exterior of the Tidewater House in Easton MD

Explore Historic Saint Michaels

A gem on the Eastern Shore of Maryland, Saint Michaels history is closely tied to the maritime heritage of the region. Located on the Miles River, this waterfront enclave is often regarded as one of the Eastern Shore’s best small towns.

Stroll through the town’s historic district along North and South Talbot Streets, where you’ll find well-preserved 19th-century buildings, unique boutiques, and gift shops offering local art, crafts, and Chesapeake Bay-themed items.

Storefronts in Saint Michaels MD

Savor seafood and other delicious cuisines at one of the town’s delightful waterfront restaurants, some of which offer outdoor seating with picturesque views. A visit to Saint Michaels wouldn’t be complete without a meal on the water at the Crab Claw. Make yourself comfy and get ready to feast on Maryland Blue Crabs offered steamed and seasoned by the dozen. Not up for the work involved in cleaning these delicacies, then perhaps you would prefer a lump crab cake or a soft shell crab sandwich. 

If you haven’t gotten enough of the view, take a stroll along the scenic Miles River. Enjoy views of the town’s harbor filled with boats and sailboats.

Marina and buildings along the Chesapeake Bay in St. Michaels MD

Spend a day on the water. Rent a kayak or paddleboard and explore the tributaries of the Chesapeake Bay or go sailing on a traditional skipjack. Visitors can also enjoy the water by taking a guided tour or a boat cruise to learn more about the town’s history and the Chesapeake Bay’s ecosystem.

Learn about Maritime History and the Chesapeake Bay

There is no better place to learn and experience the maritime tradition of the region than the Chesapeake Bay Maritime Museum (CBMM). For 50 years, CBMM has been telling the story of the Chesapeake Bay and those who have worked and lived along the Bay, from watermen to boat builders. Recognizing that the European settlers were not the first to have thrived here, the museum also delves into the relationship the Native Americans had with the bay.

This year (2023) the museum will open its new State of the Art Visitor Center. The new center will include interactive exhibits and is meant to be inclusive of all.  So even if you’ve visited in the past, it is time to return and see what’s new. We were lucky enough to get a sneak peek at what’s to come. It will be worth the wait.

The new Chesapeake Bay Maritime Museum in Saint Michaels MD

But you can still enjoy your favorite CBMM exhibits. The campus includes numerous historic buildings that hold an extensive collection of artifacts, vessels, and displays highlighting the various aspects of life on the Chesapeake Bay. Visitors can explore historic boats and vessels including traditional workboats, sailing vessels, and recreational boats.

The museum’s waterfront campus also includes a working boatyard, where visitors can see traditional boat-building techniques in action. And be sure to say “hello” to Edna, the shipyard kitty.

The boatshop at the Chesapeake Bay Maritime Museum in Saint Michaels MD

Learn about the region’s seafood industry, including harvesting oysters and crabbing. While you may know that blue crabs are critical to the region’s economy, you may not be aware that oysters are a foundational commodity as well. Your visit to the CBMM will leave you with a better understanding of both industries.

But it’s not all about the water. While visiting the museum be sure to stop by the Heirloom Garden near the Log House. The garden features historically accurate plants from the 17th, 18th, and 19th centuries. All the plants within the plots represent crops that would have been cultivated by indigenous people, enslaved and free Africans, and white Europeans during the time period. 

CBMM offers a range of educational programs, workshops, and events for visitors of all ages. These programs often focus on traditional maritime skills, like tonging for oysters (yes, that’s what it’s called and, like me, you can give it a try during your visit), environmental stewardship, and the preservation of the Chesapeake Bay’s unique ecosystem. Research and conservation are central to the work of CBMM.

Heirloom garden near the Log House at the Chesapeake Bay Maritime Museum

The museum’s mission is to preserve and explore the history, culture, and environment of the Chesapeake Bay and its surrounding communities. It aims to inspire an appreciation and understanding of the Bay’s rich heritage. A cultural institution, CBMM is a popular attraction for both locals and tourists alike. 

Take the Oxford-Bellevue Ferry 

Move away from the hustle and bustle of Easton and St. Michaels (If that’s even a thing on the Eastern Shore) and head to the historic town of Oxford. But rather than driving to this lovely little town, hop on the Oxford-Bellevue Ferry, the nation’s oldest privately owned ferry service!  

If you’ve read my article, The 26 Best Things to Do in Salisbury Maryland, you might be thinking that I told you the Whitehaven Ferry was the oldest. But you’d be mistaken. That is the “oldest continually operating ferry.” 

So, while the Oxford-Bellevue Ferry, established in 1683 is older, there have been some breaks in its service over the past 300+ years. 

Loading area for the Oxford-Bellevue ferry in Bellevue MD
By Famartin – Own work, CC BY-SA 4.0, https://commons.wikimedia.org/w/index.php?curid=119562018

The ferry is a delightful way to get across the river, even on a cloudy and dreary day like the one when we made our crossing. 

This 9-passenger car ferry crosses the Tred Avon River in approximately 10 minutes and runs daily from April to October beginning at 9 a.m. with its last run before sunset (For exact times call (410) 745-9023.). Ferry crossings continue through November but only on Saturdays and Sundays.

Unwind in Idyllic Oxford

One of the oldest towns in Maryland, this idyllic waterfront enclave is listed on the National Registry of Historic Places. This tiny town which covers less than one square mile in total, was once an international seaport.

Today the town is mostly residential consisting of historic homes and inns, such as the colonial Robert Morris Inn. Throughout town, you will find a cafe, an ice cream joint, vintage shops, a post office, a few churches, marinas, and waterfront eateries. Highlights include the Oxford Museum, dedicated to the town’s 340-year history, and the Oxford Market, an award-winning deli. Oxford is the perfect place to unwind and enjoy the bay breezes. 

Marina and boathouses on the water in Oxford, MD

As you stroll around this tiny hamlet, watch for picket fence sections painted with Eastern Shore-themed images. These are part of an annual auction that supports local causes. Each year participating organizations contribute an artistically painted section of picket fence.  They are displayed throughout Oxford all summer and then auctioned in the fall. The organization that furnished the art piece, keeps the proceeds. 

Oxford Maryland Picket fence Auction item

Spend a Day at Denton’s Artsway

Located less than 30 minutes from Easton, this state-designated Arts & Entertainment (A&E) District, encompasses 90 acres of shopping, dining, art galleries, public art, and performance space downtown.

As you stroll Denton’s quaint downtown keep an eye out for the various public art installations including painted quilt blocks that are part of the Harriet Tubman Underground Railroad Byway, mosaics, and the lifesize baling wire sculpture titled The Musician and the Muse.

The arts and entertainment district in Denton, MD

Visit the Fiber Arts Center of the Eastern Shore (FACES) (7 North 4th Street), a destination for fiber artists and fiber art enthusiasts. You will find one of those quilt blocks here.

As you make your way along the Artsway, stop and enjoy the Denton Community Garden, a lovely garden space that is not just beautiful but also acts as an outdoor classroom.

Mosaic on a brick wall in Denton MD

A visit to The Foundry (401 Market Street) is a must. This gallery, with community classroom space, features artwork from over 40 local artists in a variety of media. It’s the perfect spot to find a unique gift or souvenir that captures the essence of the Eastern Shore.

Stop in at Craft Bakery and Cafe (12 S. 3rd Street) for a delicious treat and a cup of coffee made by Night Kitchen Coffee which is located on the premises.

Wire sculpure of a guitarist in Denton MD

Get in Touch with Nature at Adkins Arboretum

The perfect companion to your visit to Denton is a side jaunt to Adkin Arboretum, a 400-acre, one-of-a-kind nature reserve dedicated entirely to plants indigenous to the Mid-Atlantic coastal plain. Surrounded by the nearly 4000-acre Tuckahoe State Park visitors will find diverse natural habitats, including woodlands, meadows, wetlands, and streams. Those curious about horticulture and natural landscapes will find a collection of native trees, shrubs, wildflowers, and grasses.

Start your visit at the Visitors Center which holds educational displays, art exhibits, and more. Here you can find out what’s in bloom, pick up a map, and one of two audio tours. Choose between an educational and entertaining tour with 35 stops, each providing a short lesson about the plants and ecology, or the tour exploring the relationship between nature and the Underground Railroad.

Sign at the entrance to Adkins Arboretum near Denton

Visitors can meander along the arboretum’s 5 miles of trails that wind through a wetlands boardwalk, meadows, and forested areas imparting a tranquil environment to enjoy. As you wander you may encounter some amphibians such as frogs and turtles, a variety of avian friends, deer, and other woodland creatures. 

Bring a book to read and grab one of the big red chairs scattered throughout. Or forget the book and enjoy listening to the rustling leaves, the babbling stream, birdsong, tree frogs, and cicadas. 

Red Chairs invite guests to stay awhile at the entrance into the visitor center at Adkins Arboretum

Kids will love visiting with the goats at their winter barn,  learning through play in Emily’s Garden, and the First Light Village a play area made from natural materials featuring wigwams, a turtle-shaped tree stump ring, and a snake balance beam all tucked within an upland forest. 

Supporting an extensive collection of native trees, shrubs, wildflowers, and grasses, the arboretum provides a valuable resource for those curious about horticulture and natural landscapes. Additionally, Adkin hosts a variety of seasonal events, including plant sales, art exhibitions, and nature-inspired festivals. These events add to the cultural and educational appeal of the arboretum and are great opportunities to engage with the local community.

Visit Old Wye Grist Mill

Once a common site, grist mills have given way to industrial milling apparatus. Therefore,  the opportunity to see the oldest continually operating mill in the country is a rare treat. The Wye Grist Mill is a water-powered grinding facility dating back more than 300 years. Situated on the upper Wye East River, this wood-framed mill is listed on the National Register of Historic Places. 

In addition to its 3-centuries of history, in the early 1800s, the mill began using what is known as the Oliver Evans Process, making it one of the first fully automated mills. That technology is still in use at the mill today and visitors can observe the process on Grinding Days.

Wye Mill
Image by Preservation Maryland, Wye Mill, side, CC BY-SA 2.0

The mill’s preservation and operation are the work of the Friends of Wye Mill, a fully volunteer organization. If you wish to support their continuing efforts, you can purchase fresh ground flour, cornmeal, jam, honey, maple syrup, and Old Wye Mill memorabilia from the Mill Shop or leave a donation. 

The Mill is open to the public from May through October, Wednesday to Saturday 10 am to 3 pm, and Sunday 1 pm to 3 pm.  Grinding Days are the first and third Saturdays of every month.

Learn about the Quakers at Third Haven Friends Meetinghouse

The oldest frame worship place in the United States, Third Haven Friends Meeting has occupied this property since 1682 when a 3-acre parcel of land was purchased from from John Edmondson. Two years later the first Meeting House was completed and remains in use to this day.

The focal point of the property is the Old Meeting House but the property also includes the brick meeting house built in 1880, the Common Room, located behind the brick meeting house, “Annie’s Cottage,” used as a workshop and storage, the two-bedroom caretaker’s cottage, and an open storage shed. While here, visit the burial grounds which have been in use since the late 17th- century. 

Interior of the Third Haven Meeting House in
Image by, Preservation Maryland – Third Haven Meeting House, interior, CC BY-SA 2.0

Quakers value simplicity which is reflected in their place of worship. Sit on one of the plain wood benches, take in the quiet, and get a sense of how they have worshipped for hundreds of years.

If you have never attended a Meeting for Worship (Quaker worship service), I encourage you to attend. It will likely be different from any other religious service you’ve experienced in the past. There are no sermons or rituals, and rarely readings. It is about contemplation and community.

Services are held at 10 a.m. on Sundays and 5:30 p.m. on Wednesdays.

Ag-Tourism at Tuckahoe Steam and Gas Association

Maryland’s Eastern Shore is as connected to its agricultural heritage as it is to its maritime culture. Out of a desire to preserve those rural roots grew the Tuckahoe Steam and Gas Association

This all-volunteer organization collects, restores, exhibits, and operates antique agricultural equipment. The group’s massive collection housed in 12 buildings on 60 acres includes steam engines, gas and oil engines, farm equipment, and more. 

Tractors at the Tuckahoe Steam and Gas Association
Photo by, Alex Handy, CC license

Additionally, visitors can visit the Rural Life Museum which showcases artifacts related to farm life, the Sawmill, and the Machine Shop. Open the 1st Saturday of the Month from May through October from 10:00 AM – 4:00 PM. Additionally, the group hosts an annual show held on the grounds during the July 4th weekend. You can also catch them at several events such as tractor pulls and rodeos throughout the year.

Pickering Creek Audubon Center

The Pickering Creek Audubon Center, located near Easton, Maryland, is a remarkable environmental education and conservation center situated on a pristine 450-acre property not far from Easton. The center features a network of well-maintained trails that wind through a diverse range of habitats, including woodlands, wetlands, meadows, and creeks. These trails are suitable for hiking, birdwatching, and wildlife observation. 

Canadian Geese flying
Image Credit: Chesapeake Bay Program, CC License

A renowned birding destination, the center’s varied habitats provide critical stopover and nesting areas for a wide range of bird species, including migratory waterfowl, songbirds, raptors, and shorebirds. While here, visitors can observe the capture, banding, and release of birds. This research contributes valuable data to our understanding of bird migration patterns and population dynamics.

Mural at the Pickering Creek Audubon Society
Photo credit: Chesapeake Bay Program, CC License

Pickering Creek Audubon Center actively engages in conservation efforts to protect and restore critical habitats in the Chesapeake Bay region.

Get Outdoors at Blackwater National Wildlife Refuge

Another wonderful stop for outdoor enthusiasts is the Blackwater National Wildlife Refuge. Often referred to as Blackwater NWR, this nature preserve covers approximately 28,000 acres and contains one-third of Maryland’s tidal wetlands, making it ecologically significant. It is known for its diverse wildlife, including birds, mammals, reptiles, and plant species making it a popular destination for nature photography.

Shorebirds at sunset at Blackwater National Wildlife Refuge
Photo Credit: Chesapeake Bay Program, CC License

Bring your binoculars because Blackwater NWR is renowned for its exceptional birdwatching opportunities, particularly for migratory species including eagles, ospreys, herons, and waterfowl. It is a critical stopover point along the Atlantic Flyway, making it a prime spot for bird watching.

Grey Heron fishing in the marsh
Photo Credit: Chesapeake Bay Program, CC License

Wildlife fanciers can drive, walk, or bike along Wildlife Drive, a 4-mile paved road along the Blackwater River offering views of the refuge. Those seeking a more immersive experience will find miles of nature trails, waterways for kayaking, as well as, 20 and 25-mile bicycling routes.  

With so much to do in the Easton area, you will find reason to return again and again.

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