Annapolis Pride Parade and Festival moved to October for second year in a row

For the second year in a row, the Annapolis Pride Parade and Festival will happen in October instead of June.

The festivities, scheduled to take place on Oct. 3, come on the heels of an “anomaly” year for the celebration, according to Ray Feldmann, a local pride organizer.

Since its inception in 2019, the Annapolis Pride Parade has been held in June. That was until it suddenly changed last year.

Organizers initially hoped to hold the events in late May to avoid competing with other regional celebrations. They were just about ready to execute when predicted thunderstorms, hail and high winds forced them to postpone their hallmark event until October.

Moving it to the fall allowed the parade and festival to take place in cooler temperatures, and October was previously considered LGBTQ History Month, Feldmann said. But even then, there were snafus, and the city saw fewer people participate than the nearly 10,000 that had attended in previous years.

Feldmann was not entirely sure why attendance was lighter, but said the parade ended up falling on the same day as a No Kings rally, which likely drew away some people, he said.

“There are so many factors. It’s the weather and other events happening that day. You just never know,” he said.

Now, organizers are trying their luck a second time, holding the flagship pride festival in October. Depending on how it goes, organizers will assess whether to revert to having the parade in June in 2027.

There may be conflicting events again this year, given that there are two boat shows and two Naval Academy football games in the city in October.

While the main event is slated for the fall, there will still be plenty of celebrations throughout Annapolis this month.

Feldmann is particularly excited about the debut of the first-ever Annapolis Pride fashion show on June 12 at Groundswell Yoga on Maryland Avenue, which will be followed by a reception with an open bar, music and silent auction at Cupla Boutique.

The silent auction will feature two original dress sketches and an autographed copy of Christian Siriano’s newest book, all of which are being donated by the award-winning fashion designer.

“We are very excited,” Feldmann said. “We just want to see how the community responds to October, and that will help decide what we do in 2027.”