Last Updated on December 9, 2023
Picture a charming small community, exuding the warmth of old-town hospitality with just the right modern flair. Welcome to Easton, the beating heart of Maryland’s Eastern Shore, where the harmonious blend of Federal and Victorian architecture intertwines seamlessly with a thriving world-class arts community.
The roots of Easton trace back to 1710 when the Assembly of the Province of Maryland established a county courthouse to serve the hardworking farmers and sea merchants navigating the waterways of the Chesapeake Bay. This pivotal moment ignited a series of developments, including the birth of the first newspaper, federal offices, banks, and the construction of the inaugural brick hotel in 1786 – collectively giving rise to the vibrant town of Easton.
Fast forward to the present day, and Easton has evolved into a flourishing community of over 16,000 residents on Maryland’s Eastern Shore. Visitors are welcomed with a plethora of options, from indulging in fine dining experiences to immersing themselves in theater, concerts, and festivals. Outdoor enthusiasts can explore a variety of adventures, while those seeking a more laid-back experience can bask in the natural beauty of the tidewater area.
My recent visit to Easton was nothing short of enchanting, and I can’t wait to share the highlights of this growing gem on Maryland’s Eastern Shore, where history meets modern vibrancy in perfect harmony.
Academy Art Museum
The Academy Art Museum is the cultural anchor of Easton. Its mission is to advance the knowledge, practice, and appreciation of the arts and to enhance cultural life on the Eastern Shore. In doing so, the museum boasts an honor granted to only 5% of U.S. museums—accreditation by the American Alliance of Museums.
This distinction brings high-quality exhibits, artists, and musicians to the facility including shows for Andy Warhol and Richard Diebenkorn.
The museum is also a community resource for educational workshops such as pastels and drawing fundamentals. You can participate in dance lessons and lectures.
There is a commitment to youth via after-school activities and home art classes.
The museum also collaborates with other organizations to host events and festivals year-round such as the annual Waterfowl Festival, Plein Air Competition, and Arts Festival, Chesapeake Film Festival, Chesapeake Chamber Music Festival, and many others.
More than a community theater, the art-deco Avalon Theater hosts concerts, theater and symphony orchestras emphasizing local talent and national acts. The venue, run by the non-profit Avalon Foundation, fosters several community events at the theater and around the town, such as Easton’s Farmers Market and the 4th of July Festivities.
The 400-seat theater sits under an 18-foot dome. There is also a 60-seat cabaret-style music listening room for more intimate performances.
The Avalon simulcasts the “Met: Live in HD” from Lincoln Center in New York City, bringing opera to Easton.
In 2020, an outdoor venue, the Stolz Pavilion, opened, showcasing live music.
The Avalon Theater again has found a way to offer a Summer Concert Series to the community by partnering with local hotels. Live music will be paired with three-course prix-fixe meals to enhance the dining experience.
Plein Aire Easton Art Festival
If painting outdoors or en Plein air sounds fun, then a trip to Easton each July is in order. Plein Aire Easton is the largest juried Plein air competition in the United States. Throughout the event week, artists are spotted intensely focusing on their easels around town and the surrounding countryside. It all cumulants in works for sale displayed for everyone to enjoy.
The Quick Draw is also a crowd-pleaser. Artists have two hours on Saturday morning to paint an original piece, then rush at the sound of the bell to Harrison Street for judging.
Those in the hunt for a one-of-a-kind piece also flock to Harrison Street in an artist feeding frenzy to buy one of the 200 plus paintings.
With over 40 species of geese, ducks, and swans, Maryland has a long tradition of waterfowl hunting. The Waterfowl Festival and its organization are dedicated to wildlife conservation, promoting wildlife art, and celebrating life on the Eastern Shore. The event, held each November, is part sportsman’s expo and art show with larger-than-life wildlife carvings, fine art, and crafts.
There are educational raptor demonstrations and bird calling contests. People of all ages gather to see giddy dock dogs compete by jumping for distance or height from a dock into a pool of water.
Then there is always Maryland seafood to enjoy, such as crab soup, crab cakes, and other local treats.
Agriculture and harvesting oysters dominated Maryland’s Eastern Shore in the 1800s. Both people living on the shore and the bounty it produced were transported via the Maryland and Delaware Railroad, which ran through the small towns, including Easton.
Today, the abandoned rail line has been transformed into a 2.5-mile trail that connects with historical downtown. The trail is accessed by walkers, joggers, and cyclists. For a piece of railroad history, visit the original depot now converted into a museum located at the trail’s midpoint.
Idlewild Park is a phenomenal place for the kids to cut loose in a well-designed community-built complex. On any given day, little ones are happily swinging away, exploring the forts, and using the climbing wall.
The Talbot County Garden Club maintains a Children’s Garden featuring a child-size boat, oyster shell-shaped maze, fountains, and other fun activities.
There is plenty of shaded areas to relax and enjoy this tranquil space or have a picnic lunch. Or you can stretch your legs on the 1/4-mile track or play a match on the basketball and tennis courts.
Chesapeake Bay Balloon Festival
The Chesapeake Bay Balloon Festival is a lively family event held late summer at Triple Creek Winery. The annual festival includes tethered balloon rides, live entertainment, crafts, and a kid’s zone.
Food trucks and food vendors are there serving up candied bacon, funnel cakes, burritos, and Maryland crab soup. Wine tasting or sales by the glass and bottle are also available from the winery. Or bring a blanket and have a picnic while waiting for the evening balloon glow where hot air balloons come alive at dusk.
Upscale and funky boutiques fill Easton’s historic downtown. This tiny shopper’s paradise includes colorful home goods at Dwelling & Design and mid-century staples at Easton Antiques & Art Gallery. Find the latest clothing trends at Lizzy Dee, Dragonfly Boutique, Sailor, or stop in at Levity to chat with the owner who is happy to share her favorite things to do here.
Browse the many art galleries such as Troika Gallery or make something new again at Vintage Books and Fine Art. Cracker Jacks contains toys, games, and educational goods guaranteed to stimulate young minds.
There are also fine food markets such a Piazza Italian Market, where pantry staples, meats, and cheeses are hand-selected and imported from Italy.
Talk to anyone in Easton, and they will happily recommend their favorite restaurant. However, one resident describes the food scene best: metropolitan.
While you can find fantastic Maryland-style crab cakes at Hunter’s Tavern or Legal Assets, you will find deluxe dining here too. Sunflower and Greens serve up bright salads in a cheery contemporary space. Alfresco dining flourishes along Washington Street at Doc’s Downtown Grille and Scossa Restaurant and Lounge.
Check out the homestyle meatloaf at Docs and the Mediterranean-style Italian fare at Scossa’s.
For a little smokey BBQ or brisket, stop by Rude BBQ.
If you’re in the mood for fine dining, make a reservation at the elegant Bas Rouge. Top everything with a sweet treat at Bonheur pies and ice cream. They serve the most fantastic root beer float in a gorgeous room with Chinoiserie-style hand-painted wallpaper.
Work off your meal and enjoy the outdoor activities famous in this area. The Eastern Shore is a sailing mecca thanks to the Chesapeake Bay rivers and inlets. Whether exploring by boat or kayak, you’ll be sure to see blue heron, egrets, waterfowl, and, if you’re lucky, an American bald eagle.
Thanks to many flat, quiet country roads, the area is a bicycling destination. One of the most famous routes is the Oxford Loop, a 33.5-mile scenic loop circling Easton, farmland, neighboring towns, and a ferry ride across the Tred Avon River. Bike rentals are available are several shops around town if you feel inspired.
Try your hand at curling at the Talbot County Community Center for something different. The Chesapeake Curling Club teaches throwing stones on ice and sweeping to score points. If that’s not your idea of fun, the community center also has an indoor ice-skating rink with public ice-skating sessions.
Blackwater National Wildlife Refuge
No trip to the Eastern Shore would be complete without an excursion to Blackwater National Wildlife Refuge (NWR). Located about 27 miles from Easton, the refuge was created in 1933 as a migratory bird sanctuary along the Atlantic Flyway. It features forests, brackish tidal marshes, shallow water habitats and is designated as an Internationally Important Bird Area.
The refuge can be seen by bicycle or car via a one-way loop called Wildlife Drive. Open dawn to dusk, the paved road winds past bodies of water and dense forests populated with loblolly pines.
These pines give haven to nesting American bald eagles, which you cannot miss as the nests are four to five feet wide. Blackwater NWR is home to the largest concentrations of bald eagles on the East Coast outside of Florida.
Several trails and observation decks are available along Wildlife Drive.
Drive slowly, or you’ll miss the tiny turtles sunning themselves on a rock in the water or a screech owl hidden amongst the branches. Traffic stops, people gather and crane their necks to spot this cleverly camouflaged little owl.
There are always many wildlife species to see throughout the year, ranging from Delmarva fox squirrels, owls, hawks, osprey, swans, snow geese, turtles, nutria, muskrats, herons, egrets, and ducks.
Oxford and St. Michaels
Oxford is a tiny little waterfront town eight miles from Easton that packs a big punch. Until the American Revolution, the town was a productive international shipping port. In the 19th century, Oxford housed the Maryland Military and Naval Academy. Young officers lived in the Academy House, which still stands today.
With its historical significance as one of Maryland’s earliest towns, Oxford today is a place to slow down and enjoy the Town Park scenery. Grab a pint, hang out with the locals, and watch the sunset on the Tred Avon River at Doc’s Sunset Grille.
For something warmer, Oxford Social serves up the local favorite’s Rise Up Coffee. Or select from a flavor of the day from the creamiest homemade ice cream around at the Scottish Highland Creamery and ride on American’s oldest privately owned ferry, the Oxford-Belle Ferry.
Situated on the Miles River, about 10-miles away, the town of St. Micheals also has a place in Maryland agriculture, shipbuilding, and seafood processing industries. The Chesapeake Bay Maritime Museum is located where these buildings once stood and features Hooper Strait Lighthouse and Maryland’s unique waterman history.
You could spend the day wandering up and down the side streets taking in the beauty of colonial style and Victorian homes that thrived in this community. There are numerous shopping and dining opportunities on Talbot Street.
St. Michaels also is home to local tasting rooms at Eastern Shore Brewing, St. Michael’s Winery, and Windon Distilling featuring Lyon Rum.