It is especially apparent in the summer time why the Eastern Shore is often called “the Land of Pleasant Living.” Summer brings festivals and other special events throughout the nine counties of the Shore. It’s a time when people of all ages can have fun together. In this article. I will focus on the period from Memorial Day weekend through June 30.
The Chestertown Tea Party takes place from Friday, May 24 through Sunday, May 26. It celebrates the tradition of Chestertown’s expression of solidarity with fellow patriots in Boston. The festivities begin on Friday evening 5pm-9pm with an old-fashioned block party at Wilmer Park on the waterfront. On Saturday morning at 10 am, there is a colonial parade on High St. in downtown Chestertown and at 2 pm a reenactment of the original event. Throughout the day there are food and craft vendors, music and activities for children.
On Sunday, May 26 the Festival continues with a Beer Fest, live music, food and craft vendors in Wilmer Park. At 2:30 visitors will enjoy the annual Raft Race, a race of rafts made of non-nautical materials. Come and have a laugh!
A Memorial Day Parade takes place on Flower St. in Berlin, Worcester County on May 27 from 11 am until noon.
Also on May 26 from 12-4 pm in nearby Rock Hall there is “Porch Fest”, designed to bring local musicians and neighborhoods together. The music is all free! Then on Monday, May 27 at 10 am you may end your Memorial Day celebration with Chestertown’s annual Memorial Day Parade on High St, downtown.
The Heart of Crisfield Festival in Somerset County is scheduled for May 25 in the Crisfield Arts and Entertainment District. There will be music, art, food and drinks at multiple locations throughout the day. On May 26 from noon until 4 pm at the Crisfield City Dock, attend the 32nd Annual Softshell Festival and Waterman’s Hall of Fame. The event features soft-shell crabs and crab cakes, music by the Going Coastal Band as well as local artisans and vendors.
Other Kent County events in early June are the Antique Airplane Fly-In at Massey Aerodrome on Saturday, June 1, 10 am – 2 pm, Maryland Line Rd., Massey. On the same day at the Rock Hall Marina at 8 am there is the Rock Hall Triathlon beginning at 8 am. On June 7 – 9 fishermen may want to enjoy the Guardian of the Pearl Rock Fish Tournament at the Rock Hall Bulkhead.
June 1 marks the second annual Janes Island Paddlefest at the Janes Island State Park in Crisfield. The event begins at 7:30 am. Events include guided paddles, a poker run paddle, a campfire on the water, food, music, pontoon boat rides, a coastal clean-up, as well as children’s activities and nature crafts.
Chestertown’s National Music Festival begins on June 2 and continues through June 15. The concerts take place at various venues and times. Tickets are required for many events, but visitors may attend rehearsals free of charge. For a schedule, go to https://nationalmusic.us/
Thursday evening June 6 and June 13 at 7 pm from the Queen Anne’s County Dept. of Parks and Recreation sponsors “Thursdays in the Park.” On June 6th, Kiti Gartner & the Drifting Valentines (Western Swing, Rockabilly) perform at the Matapeake Beach Clubhouse. On June 13th the band is Philip Dutton & the Alligators / (Louisiana music from Satchmo to Chenier) at the Cascia Winery.
For more classical music consider Easton’s Chesapeake Chamber Music Festival which runs from June 7 through June 15 at the historic Ebenezer Theatre on South Washington St. For a schedule of concerts and other information go to chesapeakemusic.org
June 15 is also the date of Salisbury’s Eastern Shore Juneteenth celebration of the African American experience. Events are in downtown Salisbury, but no schedule available at the time of publication.
Celebrate Father’s Day by attending the 36th Antique & Classic Boat Festival and Coastal Arts Fair at the Chesapeake Bay Maritime Museum in St. Michaels, Talbot County on June 14-16. The theme this year is “It’s all about fishing.” The event is sponsored by the Chesapeake Bay Chapter of the Antique & Classic Boat Society. There will be a wide-range of vessels on display. For more information and purchase of tickets go to https://cbmm.org/event/antique-classic-boat-festival-the-arts-at-navy-point/2023-06-16/.
On Saturday, June 29 Salisbury celebrates Salisbury Pride Parade and Festival, a celebration of diversity and unity. The event includes music, vendor booths, exhibits and food. For more information, go to https://www.salisburyprideparade.com/
This is by no means an exhaustive list of June events, but it does represent an exhaustive online search carried out in early May and covers the major festivals. See Common Sense in June for a listing of events covering July 1 through September 21.
A native of Wicomico County, George Shivers holds a doctorate from the University of Maryland and taught in the Foreign Language Dept. of Washington College for 38 years before retiring in 2007. He is also very interested in the history and culture of the Eastern Shore, African American history in particular.
Title image: Pond at Pickering Creek Audubon Center, Talbot Co. Photo: Jan Plotczyk