There’s a lot happening on the Eastern Shore in 2023! Come see what all the excitement is about!

39th Annual Oxford Fine Arts Fair May 19th – A prestigious juried exhibit that draws a wide selection of regional collectors as well as from major cities along the Eastern Seaboard. The much-anticipated annual show is well known throughout the area and celebrated as the season’s “kick-off” for art lovers. Tickets available here:

Cambridge Classic Powerboat Races May 20th, 10:30 – 5:00. Where: The races happen on Hambrooks Bay, off the Choptank River in Cambridge, Maryland. The Country’s longest-running powerboat races happen right here in Dorchester County! This will be the 111th Cambridge Classic Powerboat Regatta on the Choptank River.

2nd Saturdays in Downtown Cambridge: This monthly celebration in downtown Cambridge features free art gallery receptions, as well as specials in the independently owned shops and great dining. Shops and galleries are open all day and into the evening. As always on Second Saturday, downtown’s restaurants will be busy, so call ahead with your dining reservations.

The Eastern Shore Sea Glass and Coastal Arts Festival: April 22 – 23 2023: More than 90 artisans attend the campus of the Chesapeake Bay Maritime Museum in St. Michaels, many from the local Delmarva area, and others traveling from as far away as California who will exhibit and sell coastal and sea-glass related jewelry, home décor, art, and more. Admission to the festival includes all CBMM exhibits, live music and much more. Visit website for tickets, list of participating artisans and schedule of events.  

Chestertown Tea Party Festival: May 26 – 28 2023: On Saturday – Tea Toss Reenactment, Colonial Parade, Street Party, Raft Race, Street Performances, Colonial Crafts, Strolling Musicians, Local Fare, 5k & 10 mile run – entertainment, education and fun for the whole family. On Sunday the Festival moves to  Wilmer Park from noon to 4 p.m. Beer Fest featuring local craft brews, live music, artisan craft vendors, plenty of children’s activities and the infamous Raft Race!

Plein Air Easton Art Festival: July 15 to 24, 2023: The Plein Air Easton is the largest and most prestigious juried plein air painting competition in the United States.  Artists from all over the United States venture from their studios to paint by the river, along roadsides, in town, and still life in their natural setting. Besides watching the artists at work, there is a dynamic competition, galleries, and festival feel which is fascinating to see!

Ironman Triathlon in September: Be part of one of the world’s most grueling endurance events which takes place  in neighboring Dorchester County. This triathlon challenges participants from all over the world by making it through 140.6 miles all in one day: A 2.4 mile swim in the Choptank River, a 112-mile bike ride around Dorchester County, and a 26.2-mile run which all takes place in Cambridge. The half marathon Eagleman takes place in June. We are proud to host athletes from around the world for both events.

Easton Waterfowl Festival: November 10 – 12, 2023: For three days every November, between 18,000 and 20,000 visitors discover the best of local wildlife, nature, art, heritage, food, and fun at the Waterfowl Festival.

Skipjack Nathan Sails
Skipjack Nathan of Dorchester offers public sails on the Choptank River aboard an authentic oystering vessel (Maryland’s state boat!) most Saturdays, starting May 13
Riverboat Cruises
Choptank Riverboats offers lunch or dinner, crab feast, murder mystery, and sightseeing cruises from May 14 through mid-October.
plein air