In 2019, the first LGBTQIA+ pride celebration on the Eastern Shore was held in Chestertown, Maryland. Members of PFLAG of Mid-Shore Maryland organized the event including Linda Dutton, Jim Bogden, Lynn Brennan and Claire Hanson brought the festival to life. With the support of the community and notable participants like former Chestertown Mayor Chris Cerino, Heather Mizeur, and Kennedyville native and New York City drag queen Marti Gould Cummings the festival drew visitors from all over the Eastern Shore.
In 2022, the Delmarva Pride Center organized the Delmarva Pride Festival in Easton. The festival has grown each year and added more vendors, more performers and more activities. Likewise, the Delmarva Pride Center has expanded to include chapters…like the Kent County Chapter formed in 2025.
One of the goals of the Kent County Chapter of the Delmarva Pride Center was to bring back the Pride Festival to Chestertown. We are excited to announce that we are making that happen in 2026!
Thank you to all who have come before us to make a safe community for LGBTQIA+ and allies on the Eastern Shore. We are standing on your shoulders!
Grace Anderson-Schultz
Sasha Bank, Sponsors
Rashad Brown, Volunteers
Henry Draper, Fundraiser
Alyssa Jacobson, Sponsors
Tina Jones, Programming
Charlotte Kavina, Branding & Tech
Elle Kavina, Branding
Kelly Lindsay, Programming
Nicolle Moaney
Kyle O’Donnell, Vendors
Clara Rankin
Danni Sharkey, Fundraiser & Vendors
Francoise Sullivan, Chair
Alex Yates, Safety & Inclusion
Please use the form below to submit your vendor application or sponsorship payment. Thank you!
Trish Cleary
Clara & Brian Rankin
Animal Care Shelter for Kent County
Trudy Brown – Fiber Artist
Chestertown Recreation Commission
Chestertown Wellness Collective
Abigail & Heather Collins – Art
Democratic Club
of Kent County, MD*
Holly Heinefield
Heriz House
April Hill – Psychic
Kent County Chapter of Delmarva Pride Center
Emily Merenda Jewelry
NAMI Kent & Queen Anne’s County
Presbyterian Church of Chestertown
Rebuilding Together Eastern Shore
*The Delmarva Pride Center does not endorse any candidates. We want to encourage our community to stay informed and engaged in politics on the local and national level. To that end, local political organizations were invited to have a booth at the festival.
At Chestertown Pride, we celebrate love without limits. Together with our allies, we create a space of belonging, understanding, and action—working toward a safer and more accepting world for everyone.
Handicap parking is available in the Wilmer Park lot.
Lost and found will be located at the Welcome table.
Friday will be a party in Wilmer Park. Noise will be that of people talking and voices carrying through the park. Car noise may be heard as they pass Wilmer Park. On Saturday, there will be live performances from a central stage throughout the afternoon.
There is a parking lot next to Wilmer Park as well as additional parking across the street at Stepne Station. If you park at Stepne Station please follow these rules:
1) Only use spots that are NOT reserved by Stepne Station businesses
2) Do NOT park on the grass
3) Please pick up trash before exiting
Free street parking is available throughout the downtown area.
Dogs must be on a leash while in public spaces, including town parks, unless in a designated, fenced off-leash area. Owners are required to immediately remove any waste deposited by their dog in public areas.
Park benches are located around the perimter of the park. Visitors are encouraged to bring their own chairs and picnic blankets.
Chestertown Police will be attending pride events as a required security presence. A plain clothes officer will be at the police table. If pride patrons need to report a safety concern or crime, they can speak directly to an officer or contact a pride volunteer who will speak to officers on the patron’s behalf.
The park is grass with a paved walkway on the perimeter. The area is flat. If there is rain before the event, the park will be muddy creating potential for slippery surfaces.
Visitors, especially those with children, need to be mindful of their surroundings. Please do not let young children roam the waterfront unattended.
