Chestertown, MD — The Kent County Chapter of the Delmarva Pride Center is proud to announce the return of the Chestertown Pride Festival, a two-day celebration of LGBTQIA+ pride, community, and allyship, taking place Friday, May 1 and Saturday, May 2, 2026 at Wilmer Park.
The festival marks the return of Pride to Chestertown, building on the legacy of the region’s first celebration in 2019 and continuing a growing tradition of inclusion and visibility across Maryland’s Eastern Shore.
A Weekend of Celebration
Festivities kick off on Friday, May 1 from 5–8 p.m. with a high-energy Dance Party, followed by the main Festival on Saturday, May 2 from 1–5 p.m.
The weekend will bring together residents, families, visitors, and allies for a vibrant, welcoming celebration featuring:
- Live entertainment and performances
- Local vendors and artisans
- Community organizations and resource tables
- Family-friendly activities
- Food and refreshments
Organizers emphasize that the event is designed as an inclusive space where all are welcome, fostering connection, understanding, and joy across the community.
Pre-Festival Fundraiser at Zelda’s – April 25
In advance of the festival, the organizing committee will host a fundraising event at Zelda’s Speakeasy on April 25, 2026. The evening will feature live entertainment by Kiara Vos, silent auction and hors d’oeuvres provided by Occasions Catering, offering a lively opportunity for the community to gather in support of Pride.
Proceeds from the event will help fund festival programming, entertainment, and accessibility efforts to ensure the celebration remains free and welcoming to all.
Community Support and Sponsors
The Chestertown Pride Festival is made possible through the generous support of local businesses and organizations, including:
- Garfield Center for the Arts
- Kent Cultural Alliance
- MassoniArt
- The Chestertown Spy
- Zelda’s Speakeasy
- Trax Advantage Driving Academy
- Cross Street Realtors
- The Bookplate
- Eastern Shore Tents and Events
Their support reflects a strong and growing commitment across the region to inclusivity, community engagement, and the celebration of diversity.
Building on Community Momentum
The festival is organized by the Kent County Chapter of the Delmarva Pride Center, a nonprofit dedicated to supporting and advocating for LGBTQIA+ individuals across the region. Since its founding, the chapter has focused on building community, expanding outreach, and creating safe, affirming spaces in rural communities.
Bringing Pride back to Chestertown in 2026 represents a major milestone and reflects the continued growth of LGBTQIA+ visibility and support on Maryland’s Eastern Shore.
Join the Celebration
Community members are encouraged to attend, volunteer, sponsor, or participate as vendors. The Chestertown Pride Festival is not only a celebration, but also a reflection of a shared commitment to equality, belonging, and community connection.
Special Thanks
The Chestertown Pride Festival would like to thank the Town of Chestertown, Chief Dixon and the Chestertown Police Department, and the Chestertown Recreation Commission for their support.
For more information, visit: https://chestertownpride.com/
About the Delmarva Pride Center
The Delmarva Pride Center is a 501(c)(3) nonprofit organization serving the LGBTQIA+ community across the Delmarva Peninsula through advocacy, education, outreach, and community-building initiatives.
One Response
It’s great to see Pride returning to Chestertown! The LGBTQ+ community needs us now more than ever.