Pride · Chestertown, Maryland
Chestertown Pride Festival
2027 dates not announced yet · usually May
About Chestertown Pride Festival
The Chestertown Pride Festival in Kent County on Maryland's Eastern Shore was revived in 2026 by the Kent County Chapter of the Delmarva Pride Center, after a first celebration organized by PFLAG members in 2019. The 2026 festival at Wilmer Park opened with a Friday evening dance party on May 1 and a Saturday afternoon festival on May 2 with live performances, food trucks and local vendors.
The 2019 festival in Chestertown was the first LGBTQIA+ Pride celebration held on the Eastern Shore. It was organized by members of PFLAG of Mid-Shore Maryland and drew visitors from across the Shore, with participants including former Chestertown Mayor Chris Cerino, Heather Mizeur and Kennedyville native Marti Gould Cummings. In 2022 the Delmarva Pride Center began organizing the Delmarva Pride Festival in Easton, and it formed its Kent County Chapter in 2025 with the goal of bringing the festival back to Chestertown.
Wilmer Park is a flat, grassy space with a paved walkway around its edge, and it can get muddy after rain. Accessible parking is in the Wilmer Park lot, with more parking across the street at Stepne Station and free street parking downtown. Benches line the park, and visitors are encouraged to bring chairs and blankets. Dogs must be leashed, and families are asked to keep young children away from the waterfront.
Chestertown Police attend as the required security presence, with a plainclothes officer at a police table, and volunteers can relay safety concerns to officers. Lost and found is at the welcome table. Local political organizations were invited to have booths, though the Delmarva Pride Center does not endorse candidates.
Summarized from the organizer's own website.
What to expect
Pride events celebrate LGBTQ+ people and mark the Stonewall uprising of June 1969. Most combine a parade or march with a festival of performers, community groups, vendors and food.
Chestertown Pride Festival has included dance party, festival, live performances, food trucks and vendors.
The organizer has not announced dates for 2027 yet. In 2026 it was held May 1-2, 2026. It usually falls early May.
- Dance party
- Festival
- Live performances
- Food trucks
- Vendors
Where it happens
Chestertown Pride Festival is held at Wilmer Park in Chestertown, Maryland. It is one of 24 Prides in Maryland on this calendar.
Other nearby Pride festivals
- Oct32026Upper Chesapeake Bay Pride FestivalHavre de Grace, MD23 miles away
- Oct32026Annapolis Pride Parade and FestivalAnnapolis, MD29 miles away
- Oct9-122026Baltimore BLAQ PrideBaltimore, MD29 miles away
- JunTBA2027Baltimore PrideBaltimore, MD29 miles away
- JunTBA2027Baltimore Trans PrideBaltimore, MD29 miles away
Questions about Chestertown Pride Festival
- When is Chestertown Pride Festival 2027?
- The organizer has not announced 2027 dates yet. In 2026 it was held May 1-2, 2026. It is usually held early May.
- Where is Chestertown Pride Festival held?
- Chestertown Pride Festival takes place at Wilmer Park in Chestertown, Maryland.
- What happens at Chestertown Pride Festival?
- Events have included: dance party, festival, live performances, food trucks, vendors.
- Who organizes Chestertown Pride Festival?
- Chestertown Pride Festival is organized by Kent County Chapter of the Delmarva Pride Center. Their official site is chestertownpride.com.
- What other Prides are near Chestertown?
- The closest others on this calendar are Upper Chesapeake Bay Pride Festival in Havre de Grace, MD (about 23 miles); Annapolis Pride Parade and Festival in Annapolis, MD (about 29 miles); Baltimore BLAQ Pride in Baltimore, MD (about 29 miles).
LGBTQ-owned businesses in Maryland
See allNone are listed in Chestertown yet, so these are elsewhere in Maryland. Eat, stay and shop with LGBTQ-owned businesses while you are in town. Ownership on every listing is sourced, never guessed.
