Kent County

Fourth of July in Chestertown & Rock Hall

Independence Day brings a full slate of traditional, family-friendly festivities across Kent County. Things kick off with active public celebrations, a hometown parade, and local food vendors in downtown Chestertown. The evening concludes down at the waterfront in Rock Hall, where families can set up lawn chairs for a massive public fireworks display echoing out over the Rock Hall Harbor.

• Date: Friday, July 3, 2026

   
  Time: All day events, with fireworks scheduled at dusk.

• Location: Downtown Chestertown and the Rock Hall Harbor Waterfront, Rock Hall, MD 21661

   
  Contact: You can reach out to the Rock Hall Town Office at 410-639-7611.

Pirates and Wenches Fantasy Weekend

The lakeside town of Rock Hall gets completely taken over by swashbuckling family adventure for its popular town-wide theme weekend. The public event includes maritime history showcases, pirate costume parades for all ages, sea shanty sing-alongs, local artisans, and decorated boats packing out the harbor. It is an entirely public, town-wide festival designed to bring a little lighthearted fantasy to the dog days of summer.

• Date: Friday, August 14 through Sunday, August 16, 2026

• Time: Events start Friday afternoon and run all day Saturday and Sunday.

• Location: Main Street and the Public Harbor Waterfront, Rock Hall, MD 21661

• Contact: Get a schedule of events from the Rock Hall Town Office at 410-639-7611.

Queen Anne’s County

Thursdays in the Park Summer Concert Series

The Queen Anne’s County Arts Council hosts its continuing outdoor musical series featuring regional talent in a beautiful setting along the water. In July, the park welcomes the Blues Keepers followed a week later by the band Shredded Cheddar. In August, the public can come out to see the Ricky Wise Trio and the band Honey Sol. It is a perfect, relaxed evening for locals to bring a blanket, pack a picnic, and enjoy music outdoors.

• Date: July 9, July 16, August 13, and August 20, 2026

  Queen Anne’s County Arts Council

• Time: Every concert runs from 7:00 PM to 9:00 PM.

• Location: Cascia Vineyards and Winery Lawn, 1200 Thompson Creek Road, Stevensville, MD 21666

• Contact: Contact the Queen Anne’s County Arts Council office at 410-758-2520.

Queen Anne’s County Annual Members Fine Art Show

The local arts council opens its gallery doors to the general public for the official launch of the Annual Members Show. This community exhibition highlights a stunning collection of paintings, photographs, sculptures, and mixed media created entirely by local and regional artists living on the Shore. It provides an excellent, air-conditioned public space to view local culture and support regional creators.

• Date: Running throughout the entire month of August 2026

• Time: Open daily during standard gallery hours.

• Location: Queen Anne’s County Arts Council Center, 206 South Commerce Street, Centreville, MD 21617

• Contact: You can verify current weekday gallery hours by calling 410-758-2520.

Talbot County

Summer Cinema on the Linden Lawn

The historic Oxford Community Center sets up a giant projector screen on their pristine lawn for a series of classic, family-friendly outdoor movie nights under the stars. The public is highly encouraged to bring their own lawn chairs, stadium seats, or beach blankets. Freshly popped popcorn, candy, and light refreshments are made available to attendees to create a true vintage drive-in style experience.

• Date: Scheduled select Tuesday nights, including July 14 and August 11, 2026

  Chestertown MD

• Time: Films begin rolling right at dusk, typically around 8:30 PM.

• Location: Oxford Community Center Lawn, 200 Oxford Road, Oxford, MD 21654

• Contact: Reach the front desk of the community center at 410-226-5904.

Northern Caroline County

The 37th Annual Caroline Summerfest

This massive, completely free end-of-summer street festival takes over the heart of Caroline County for two full days of family entertainment. The event features two stages of regional and local musical acts, strolling street performers, a classic car show on Friday night, a spectacular fireworks display on Saturday night, and tons of local food vendors raising money for county non-profits. Free public parking and continuous shuttle bus transportation are provided to ensure easy access.

• Date: Friday, August 21 and Saturday, August 22, 2026

  Downtown Denton Main Street

• Time: The festival is open from 4:45 PM to 9:30 PM both days.

• Location: The 200 Block of Market Street, Downtown Denton, MD 21629

  Downtown Denton Main Street

• Contact: You can reach the Denton Main Street and festival coordinator line at 410-479-2050.

  Downtown Denton Main Street

Historical Society Semiquincentennial Art Challenge Show

In honor of the upcoming 250th birthday of our nation, the Caroline County Historical Society is holding an open public art gallery and showcase. Eastern Shore artists, makers, and students will have their historical themed creations on full display. It is a unique community gathering that blends the deep history of Caroline County with contemporary regional art, running right alongside the town’s Summerfest weekend.

• Date: Friday, August 21 and Saturday, August 22, 2026

  Downtown Denton Main Street

• Time: Open to the public from 5:00 PM to 9:00 PM in conjunction with the street festival.

• Location: Caroline County Historical Society Museum, 102 Market Street, Denton, MD 21629

• Contact: Reach out to the Caroline County Historical Society team at 410-479-2730.