An artist paints at Easton Point during the annual Plein Air Easton Art Festival, the country’s largest plein-air event.
In town, the restored Avalon Theatre, built in 1922, still regales visitors with concerts and shows.
The annual Great Chesapeake Balloon Festival takes place in August. © CURTIS BRANDT
A family takes to the Tred Avon River for paddle boarding.
Strolling on Harrison Street is a shopper's delight.
Stop into Sunflowers & Greens for a healthy lunch.
Furniture at Dwelling & Design.
A collection of home furnishings and accessories at Bountiful.
The Inn at 202 Dover serves breakfast in its glass-enclosed conservatory.
Hydrangeas make a statement in the Talbot Historical Society Garden.
The annual Great Chesapeake Balloon Festival takes place in August. © CURTIS BRANDT
A family takes to the Tred Avon River for paddle boarding.
Strolling on Harrison Street is a shopper's delight.
Stop into Sunflowers & Greens for a healthy lunch.
Furniture at Dwelling & Design.
A collection of home furnishings and accessories at Bountiful.
The Inn at 202 Dover serves breakfast in its glass-enclosed conservatory.
Hydrangeas make a statement in the Talbot Historical Society Garden.

Escapes: Festive & Artsy Easton

This gem on Maryland’s Eastern Shore offers delightful festivals and finds for foodies, art lovers and collectors

Easton has long been a gathering spot for a cornucopia of people—from the Quakers who built a meeting house there in 1682 to the art aficionados who now flock to its annual plein-air painting festival. Standing before its impressive Federal-style Talbot County Courthouse, visitors will see both a monument to the “Talbot Boys” who fought for the Confederacy and a statue honoring Frederick Douglass, who was jailed here for a few years before he escaped slavery in 1838. Both the town’s statues and its well-preserved architectural relics attest to the variety of minds and tastes that have called this spot home.

While Easton has long been a seat of commerce and government, the locals also celebrate leisurely pursuits, particularly in the arts and the sport of hunting. The fingers of the Tred Avon River just touch its borders, so there’s no real waterfront in the main town. Instead, visitors will find strollable brick sidewalks and a preponderance of Federal architecture, mixed with some well-preserved Victorian and Neoclassical structures to entertain the eye. Easton exudes stately charm and respectability, but it has a playful side too.

HISTORIC MEANDERINGS  The Welcome Center on S. Harrison Street offers a detailed map for three self-guided walking tours highlighting the town’s local treasures. The Third Haven Friends Meeting House (1682) is the oldest documented building in the state; Quakers gather in its serene interior, open to the public daily. The county courthouse still occupies the site of the original brick courthouse and jail, built by colonists in 1710. Parts of the current courthouse date back to 1794. Housed nearby in the Mary Jenkins House, an early frame structure, the Talbot Historical Society features an interactive display that reveals how local waters and land have controlled the rhythm and growth of the area.

On your wanderings, pop into the lovely Academy Art Museum, located in an 1820 Schoolhouse (academyartmuseum.org), which showcases regional artists along with a fine permanent collection. Savor a sweet treat at Hill’s Drug Store, which boasts an old-fashioned soda fountain. Overnighters can also catch nationally known comedians and musicians at the charming Art Deco Avalon Theatre (tickets.avalontheatre.com).

FUN FESTIVALS  As the largest juried plein-air painting competition in the country, Plein Air Easton (pleinaireaston.com) puts this city on the map. During the 2016 event, 58 local and far-flung artists will paint outdoors all over Talbot County from July 9 through 17.  A favorite is the “Quick Draw” event, a two-hour paint-off when visitors can watch 200 artists in action and then buy paintings they fancy. With a block-party feel, the event also offers workshops, demonstrations and a bustling artisans market.

For a bird’s eye view of the region’s winding waterways, mark your calendar for the Great Chesapeake Balloon Festival (greatchesapeakeballoonfestival.com). Held this year on August 5 and 6 at the Triple Creek Winery, the event offers tethered balloon rides rising 60 feet up, passenger balloon flights over the county and a stunning balloon “glow” with 15 hot-air balloons illuminated and afloat after dark.

Located on the migratory bird flyway, Easton becomes a mecca for the hunting community each autumn during the Waterfowl Festival (waterfowlfestival.org), taking place this year from November 11 to 13. This celebration of Eastern Shore traditions includes everything from retriever demonstrations to superb wildlife art to wine tasting. Over the last four decades, the festival has also raised millions for Chesapeake watershed habitat restoration, education and research.

ABUNDANT ARTS  With art galleries at nearly every turn—there are eight official galleries and lots of other shops featuring art work—you’re sure to find a piece that suits your palate. Owned by two artists, Troika Gallery (troikagallery.com) offers year-round events and a chance to see the owners at the easel or chat them up about the 30-plus artists whose work they show.

“Easton is an incredibly creative town,” says local artist David Grafton, whose landscapes are collected by National Gallery of Art curator Earl Powell, III. Grafton owns a working and teaching gallery, Grafton Art (graftonart.com), featuring his soul-soothing paintings of rivers, coasts, and dunes, as well as works by his students.

Nestled in a Victorian home, South Street Art Gallery (southstreetartgallery.com) displays a gorgeous collection of local landscapes that will make you pine for more time in natural settings. It’s open Saturdays or by appointment. And don’t miss the lovely Trippe-Hilderbrandt Gallery (trippehilderbrandtgallery.com) with its exceptional photography collection. Taking a monthly First Friday Gallery Walk when the shops are open late and serve refreshments is an ideal way to kick off a weekend.

CULINARY DELIGHTS  Easton’s reputation for creativity includes the culinary arts with a locavore emphasis. With its motto of “dirt to the table in one day,” the Bartlett Pear Inn’s restaurant (bartlettpearinn.com) is touted as one of the best around. Try the chef’s tasting menu with wine pairings. The Inn also recently opened a cozy bakery across the street that sells sweet and savory breakfasts and the best baguettes in miles.

Open for lunch only, the bright Sunflowers & Greens (sunflowersandgreens.com) lets you compose your own salad from such treats as roasted corn and blackened ahi tuna. Drink your fill of antioxidants at nearby Bumble Bee Juices (bbjuices.com) and assume a calming pose between meals at Blue Mat Yoga Studio (bluematyogastudio.com). Thirsty? Hit happy hour at the newly renovated Hunters’ Tavern in The Tidewater Inn (tidewaterinn.com) for two-for-one drinks and half-priced appetizers.

On the way in or out of town, swing by Rising Up (riseupcoffee.com),  a local coffee roaster known for its smooth grounds and scrumptious baked goods. The Peacock Restaurant and Lounge in the Inn at 202 Dover (innat202dover.com) specializes in classic cocktails and fine dining in a Colonial Revival mansion. For al fresco dining and a range of American gustatory options, head to Mason’s (410-822-3204).

ECLECTIC SHOPPING  When it comes to shopping, Easton has something for everyone. For furniture, antiques, lighting, and accessories, don’t miss Bountiful Interiors (bountifuldecor.com), where the name rings true through an eclectic variety of design styles on display, from the classic hunt-country look to a bright and beachy vibe. For unique light fixtures that will add an exclamation point to any room or accessories with that colorful (especially blue) touch that can tie a whole room together, visit the fabulous Dwelling & Design (dwellinganddesign.com). Both shops proffer design services, along with tile, floor and fabric samples.

Bargain seekers will thrive at Tharpe House Antiques & Decorative Arts (410-820-7525), a consignment store run by the Talbot County Historical Society featuring new and antique furniture, crystal, china and books. The eclectic Lanham Hall Design (lanhamhalldesign.com) will have you salivating over select pieces. At Trumpeter Swan (trumpeterswanantiques.com), you may unearth some classic accent pieces and that vintage decoy you can’t live without.

NOTABLE LODGINGS  The Tidewater Inn, a Federal gem at the center of town, recently upgraded many of its rooms to “premier” status. It also offers a spiffy bar and meeting rooms of all sizes. The magnificent Inn at 202 Dover (innat202dover.com) treats guests to internationally themed rooms and a full breakfast, Victorian gardens and high tea on Thursday afternoons. The highly reviewed Bartlett Pear Inn features bright, minimalist rooms and includes a full breakfast at its bakery across the street.

Amy Brecount White explores and writes about the world from her base in Arlington, Virginia.