See art in motion and ‘en plein air’ along Maryland’s Chesapeake Country All-American Road

The scenic byway plays host to an outdoor painting festival every July along Maryland’s Eastern Shore

Paintings on display. | Photo: Julie Suman

In artistic terms, the French phrase “en plein air” describes painting outdoors and is often associated with 19th-century impressionists. Today, this style allows for an in-the-moment expression of the landscape—and it’s exciting to watch a plein air artist interpret their vision onto canvas in real-time. Easels, watercolors, and artists in floppy hats line the fields and sidewalks each July on Maryland’s Eastern Shore. Prestigious painters from across the U.S. gather to create outdoors at Plein Air Easton, the largest annual juried competition of its kind in the country. 

The Quick Draw competition brings artists downtown for 2 hours, during which spectators will find easels tucked into courtyards and flowing into the street. When the bell rings, artists must gather on Harrison Street to exhibit their freshly-painted projects and those searching for a unique souvenir flock to bid on one of the pieces. The week culminates in a display of the award-winning paintings at the Academy Art Museum. In addition to festival art, the museum also houses a permanent collection featuring modern American and European masters.

the exterior of the academy art museum featuring several small buildings
Academy Art Museum. | Photo: Julie Suman

The festival is a good excuse to further explore the enchanting Eastern Shore towns in addition to Easton, including Oxford, St. Michael’s, and Tilghman Island. These small towns dot portions of the Chesapeake Country All-American Road, and Plein Air Easton spans a portion of the 400-mile-long road, weaving through Talbot County and its 600 miles of shoreline. Summertime brings verdant fields, roadside farmer’s markets bustling with produce, delightful scenery, and fresh seafood.

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Over 10 days, spectators can do more than peruse artist galleries. Education is focused on panel discussions, painting demonstrations, and live podcast recordings. Or you may strike up a conversation with the artist as al fresco painters diligently capture coastal scenes by the roadside. The festival is the ideal catalyst for a road trip—exhibits, demonstrations, and art sales from across the region inspire travel along scenic highways and nostalgic towns. Here’s where to stop along the way.

1. Easton

Easton is the hive for plein air events. Although Easton’s population hovers around 16,000 people, the small town still packs a big punch. You’ll find an active art community along with fine dining, live music, boutique shopping, and devotion to waterfowl: Plein Air Easton’s headquarters is located at the historic Waterfowl Building and a Waterfowl Festival takes place here each November. Competition paintings coalesce in Easton for viewing and sales; new pieces are added as the artists create them, so each day brings something new.  

The festival starts with a Friday night art gallery and shop walk through downtown. The town’s Federal and Victorian-style architecture glows at night and is the perfect backdrop for getting to know Easton. You can also paint alongside the artists during the Nocturne Paint Out, and overnight at the circa-1700s Tidewater Inn. And you can’t visit without a Maryland-style crab cake at Hunter’s Tavern or local rockfish at Legal Assets.

a three-story yellow inn by the water
The Robert Morris Inn. | Photo: Julie Suman

2. Oxford

On Sunday, festival activities shift to Oxford, located 8 miles from Easton. Artists spend the day out and about in town, capturing its beauty and exhibiting their day’s work at the Oxford Community Center.

A colonial town with tree-lined streets and picket fences, Oxford traces its roots back to the late 1600s. The Robert Morris Inn, established in 1710, is the oldest full-service inn in the U.S. with ties to the Revolutionary War. Sweeping water views from the Tred Avon River invite you to watch the sun go down at Doc’s Sunset Grille. Or you can continue your road trip via the country’s oldest privately-owned ferry route on the Oxford-Bellevue Ferry. Before you go, grab a scoop of homemade ice cream at the Scottish Highland Creamery.

a rocky coastline under a dramatic sky of clouds
Tilghman Island. | Photo: Julie Suman

3. Tilghman Island

You’ll find a true waterman’s village on Tilghman Island. Crabbing and oyster fishing are still a way of life on this island located 23 miles from Easton, where competition artists gather to capture images, showing the day’s paintings at the Tilghman Waterman’s Museum.

Tilghman Island juts into the Chesapeake Bay, providing extensive water views. It’s a perfect destination for sailing and fishing, and guests at the Wylder Hotel can grab a bicycle and explore the island’s nooks and crannies.

a large inn at sunset with chairs and lights surrounding water
Inn at Perry Cabin. | Photo: Julie Suman

4. St. Michaels

The Chesapeake Country All-American Road also passes through the charming town of St. Michaels. While there are no official festival events here, you may see painters capturing views of the harbor and working boats at the Chesapeake Bay Maritime Museum.

Romantic inns and fantastic dining offer additional reasons to spend time in St. Michaels. Ava’s Pizzeria and Wine Bar, with a coal-fired oven, is a perennial favorite and shoppers will also fall in love with the wide variety of goods offered in local shops, from nautical accessories to Limoncello.