Queen Anne’s County

For a fun family day, head over to Sudlersville Middle School at 600 Charles Street on Friday, April 17, 2026. They are hosting a Community Resource Fair from 4:00 PM to 7:00 PM. It’s a great way to connect with local organizations, and there are usually activities and info booths for all ages.

The Kent Island Farmer’s Market continues its year-round schedule every Thursday from 3:30 PM to 6:00 PM. It takes place at 4300 Main Street in Stevensville. It’s a wonderful outdoor community gathering where you can buy local produce, eggs, and handmade goods directly from the farmers.

Housing Authority Board Meeting On Monday, May 11, 2026, from 4:00 PM to 6:00 PM, the Housing Authority of Queen Anne’s County holds its regular board meeting. While it’s a formal administrative gathering, it is open to the public and provides a clear look at local housing initiatives and community development plans for the year.

• Address: Liberty Building, 107 N Liberty Street, Centreville, MD 21617

  Contact: 410-758-8631

Foxxtown and Terrapin Grove Tenant Council Meetings Throughout May and June (specifically May 13, May 20, June 10, and June 17), these community councils meet to discuss neighborhood improvements and local resident concerns. The Foxxtown meetings usually start at 7:00 PM, while the Terrapin Grove sessions begin at 6:00 PM. These are grassroots, community-focused opportunities to hear what’s happening in local neighborhoods.

• Address: Locations vary by neighborhood in Stevensville and Centreville, MD

• Contact: 410-758-8631 (QAC Housing Authority)

Kent County

Wings of Spring, a brand-new nature-inspired festival, makes its debut in the waterfront town of Rock Hall this April. Nestled along the scenic Chesapeake Bay, the event celebrates the annual return of ospreys and the vibrant renewal of spring.

The celebration begins with a ticketed Kick-Off Reception on Friday, April 24 from 6:00–8:30 PM at Osprey Point Inn (reservations required, followed by a fun filled day of family-friendly programming on Saturday, April 25 from 9:30 AM–4:00 PM throughout town.

Visitors will have the rare opportunity to observe ospreys in their natural habitat as they return to nest throughout Rock Hall Harbor. The festival blends wildlife education, outdoor recreation, and small-town charm, offering something for all ages.

Highlights include:

Osprey Symposium & Nature Talk

Hosted at The Mainstay in partnership with Friends of Eastern Neck National Wildlife Refuge, the day begins at 9:30 AM with “Osprey Population Trends in Northern Chesapeake Bay.” A native plants presentation follows from 2:00–3:00 PM.

Scenic Boat Tours ($35 pp)

One-hour guided tours of Rock Hall Harbor and Swan Creek depart throughout the day, offering a unique vantage point to view nesting ospreys and local wildlife. Sign up in advance encouraged. Walk-ups are welcome based on availability.

Galena Dogwood Festival In early to mid-May 2026, the town of Galena hosts its annual family-friendly festival. The Main Street area fills up with craft and food vendors, live music, and activities for children. One of the highlights is the local dog contest, followed by “Dogwood After Dark,” which features more music and evening vendors.

• Address: Main Street, Galena, MD 21635

  Contact: 410-648-5151 (Town Hall)

Eastern Neck Island Waterfowl Walk

Explore one of the region’s most treasured natural areas with a guided walk at Eastern Neck National Wildlife Refuge from 2:00–4:00 PM. Reservations required.

Wings of Spring Festival

Rock Hall, Maryland

o Kick-Off: Friday, April 24 (6:00–8:30 PM)

o Main Event: Saturday, April 25 (9:30 AM–4:00 PM)

Open to the public; activities for all ages

One of the biggest events of the year is the Chestertown Tea Party Festival, which takes place from Friday, May 22, to Sunday, May 24, 2026. The main festivities occur on Saturday in the Historic District and at the foot of High Street, including a colonial parade and the famous tea toss reenactment at 2:00 PM. On Sunday, the party moves to Wilmer Park for the Raft Race. It is entirely free to the public, and you can reach organizers at 443-924-6411.

Nature lovers should check out the Experience the Bay with Chesapeake Scenes event on Friday, May 15, 2026, at 7:00 PM. This takes place at the Lawrence Wetlands Preserve at 121 S Commerce Street in Chestertown. It’s an educational and visual presentation about the local environment.

Northern Caroline County

In Greensboro, there is a Family Fun & Resources Day on Saturday, April 18, 2026, from 10:00 AM to 1:00 PM. This is held at the Greater Impact Church at 13699 Greensboro Road. It’s a completely free event with a bouncy house, games, and free lunch for the first 100 kids. You can reach out to the Caroline Health Department at 410-479-8030 for more details.

In Denton, the Friday Night Cruise-In Car Show is back on Friday, May 10, 2026, from 6:00 PM to 8:00 PM. The 200 and 300 blocks of Market Street will be closed off to showcase classic cars and hot rods. It’s a very relaxed, walk-around event hosted by the Denton Police Department.

Denton Memorial Day Parade On Friday, May 22, 2026, at 6:00 PM, the American Legion hosts the annual Memorial Day Parade in downtown Denton. The route usually runs along Market Street from 1st to 5th Street. It is a classic small-town tribute featuring local marching bands, veterans’ groups, and community floats.

• Address: Market Street, Denton, MD 21629

• Contact: 410-479-2050

The Memorial Day Parade will take place on Saturday, May 23, 2026, starting at 6:00 PM. The parade route runs down Market Street from 1st to 5th Street. It’s a traditional small-town parade that is very popular with residents. You can call the Town of Denton at 410-479-2050 for more info.

Talbot County

In May, the Easton Farmers Market shifts into its full spring/summer gear. It’s held every Saturday from 8:00 AM to 1:00 PM in the public lot at 100 West Dover Street. Beyond just vegetables, they often have live acoustic music and local crafters, making it a nice weekend morning destination.