Queen Anne’s County

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)

Maryland Commodity Classic 2026

Agriculture takes center stage on Thursday, July 23, 2026, at the Queen Anne’s County 4-H Park, situated at 10140 Old Skipton Road, Centreville, MD 21617. Starting early at 8:00 AM, this event is a cornerstone for the local farming community, featuring equipment displays, educational sessions, and networking for those involved in Maryland’s grain and commodity sectors.

Kent County

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.

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 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.

Navigating Medicare Workshop

For a more informative session, the Caroline County Library’s Denton branch is hosting a workshop on Wednesday, June 10, 2026, at 12:30 PM. The library is located at 100 Market St, Denton, MD 21629. This public session is designed to help residents understand the complexities of Medicare coverage. You can contact the library at (410) 479-1343 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.