Pirates and Wenches Weekend
August 8 – 10, 2025
Rock Hall, Maryland
www.rockhallpirates.com

Come by land, or come by sea, and enjoy a two-and-a-half-day town-wide theme party you will not soon forget! This is a wonderful opportunity to bring your boat and anchor out on the Chesapeake Bay or raft up with your mates. There is plenty of anchorages, dockage, and raft-up space available – as well as plenty of parking for those arriving by land. This exciting event, which offers activities for all ages, is less than a tank of gas from Philadelphia, Baltimore, Washington D.C, and Northern Virginia. Costumes “Arrrr” encouraged!

Rock Hall’s Pirates and Wenches Weekend is a town-wide theme party. The weekend-long event features live entertainment and Pirate performers, costume contests, treasure hunts, kids’ activities, merchants, and more fun for the whole family.

The 29th Annual Chestertown Jazz Festival, “Jazz by the River,” is scheduled for Saturday, September 6, 2025, at Wilmer Park in Chestertown, Maryland. The festival is held from 12 pm to 6 pm.

The Festival, a division of OuterArts Maryland, Inc., combines world-class mentor musicians and gifted pre-professional apprentice musicians for an intense Festival experience the first two weeks of each June. All apprentices receive full scholarships and housing, mostly with host families in private homes. The two groups rehearse and perform side by side in orchestral, chamber, solo recital, choral, and chamber opera repertoire. In two weeks, these musicians present over 30 concerts and over dozens of free open rehearsals for music lovers from around the world.

Each year the Festival serves approximately 110 apprentices and employs approximately 30 mentors (including the Artistic and Executive Directors, who also teach). Musicians come to the Festival each year from more than 15 countries and 30 U.S. states. The average age of apprentices is 22, although some are older and have already completed their advanced degrees and begun their careers.

Concerts and free open rehearsals take place in a variety [...]

The Rock Hall Volunteer Fire Company (RHVFC) is proud and excited to host The Pearl of the Chesapeake Rockfish Tournament, a three-day event that features a two-day tournament (June 7-8) and a Captain’s Meeting (June 6). Situated on the eastern shore of the Chesapeake Bay, Rock Hall is a charming village known as The Pearl of the Chesapeake. The tournament promotes heritage, tourism, and fishing for the town while raising funds for the RHVFC which serves it and surrounding communities.

In response to the British Parliament’s closing of the port of Boston, the citizens of Chestertown, Maryland met in May of 1774 and set forth “Resolves” forbidding importing, selling, or consuming tea in Chestertown. According to local legend, residents then gathered at the town center, marched down High Street to the brigantine Geddes, which was anchored in the Chester River, and tossed her cargo of tea overboard. The annual reenactment of that event is the centerpiece of the Chestertown Tea Party Festival. The re-enactment is scheduled for Saturday at 2:00 p.m. All Festival events take place along the Chester River and in the historic district of 18th-century Chestertown, Maryland. There is no admission charge to the Festival.

Start training now for this year’s Classic Distance 10 Mile Run and 5k Run/Walk. Or join the festival-goers that line High Street each year to cheer the passing of colonial militia, marching bands, costume-garbed children, and more in [...]

Escape to Cecil County, Maryland with vibrant small towns, 200 miles of waterfront, foodie destinations, and scenic countryside providing the perfect backdrop for adventures and making memories.

Experience fabulous dishes with a Chesapeake Bay flair at award winning local restaurants along the waterfront, in the country, and on walkable main streets with shops.  Try local beer and wine, baked goods, homemade ice cream, coffee shops, farm stands, and old-fashioned candy stores.

Hike or bike 100 miles of scenic trails at State and Town parks, great for nature lovers and bird watchers.  Book a boat ride, cast a fishing line, rent a boat, or paddle Cecil County’s waterways.  Make furry friends at Plumpton Park Zoo, enjoy fun at the orchard, camp under the stars, and take a horse-back trail ride.  Watch as ships from around the globe and pleasure vessels cruise through the C&D Canal along the [...]