CHESTERTOWN — The Chestertown Jazz Festival celebrates its 25th anniversary this year with a weekend jazz lovers will remember.

To mark the anniversary, “we have one of the most incredible performers — Christian McBride,” Leslie Prince Raimond said in an interview Tuesday, Sept. 7.

The first jazz festival, which occurred in 1996, was Dr. Melvin Rapelyea’s idea.

According to Raimond, Rapelyea thought that there was no reason Chestertown couldn’t have a festival that was equal to the famed Newport Jazz Festival. Raimond said Rapelyea approached her when she was director of the Kent County Arts Council, about the first festival, and they have been collaborating on each one since.

“His devotion is what makes it happen,” Raimond said of Rapelyea.

The first Chestertown Jazz Festival was held on Friday, Aug. 30 and Saturday, Aug. 31, 1996, and included musicians like Dick Durham, Sue Matthews, the Ashley Harding Quartet, the Tom Lagana Trio and more.

Over the years, portions of the festival have taken place at the White Swan Tavern, under a small tent in Wilmer Park, at Washington College’s Tawes Theater, the Imperial Hotel, Black Eyed Susan Restaurant, the Garfield Theater, the Mainstay and more.

“It’s had various iterations,” Raimond said.

Kicking off this year’s festival, Chuck Redd will perform “A Dedication to Charlie Byrd” at The Mainstay in Rock Hall at 7 p.m. on Thursday, Sept. 9. Tickets for Redd’s performance are $25 online and in advance and $30 at the door.

Information and ticket sales are available on the Mainstay’s website at and, or call 410-639-9133.

The festivities move into Chestertown at 6 p.m. Friday, Sept. 10 with performances by the Bratcher Project and the Sholbertshire Quintet in Wilmer Park. The Friday night event will include cocktails, hors d’oeuvres and have “a festive feeling,” Raimond said. Tickets are $40.

Jazz in the Park starts at noon Saturday, Sept. 11 with a performance by the Burke Family singers, who have been performing together for over 50 years.

“We always start with a gospel group,” Raimond said. “To celebrate the roots aspect of jazz and American music in general — it’s always been very important to what we do.”

Raimond said that she’s expecting 17 members of the Burke Family singers to perform on Saturday.

“Anybody who is interested in that should be there at least five minutes before noon,” she said. “We have a schedule and we’re sticking to it.”

At 12:24 p.m., The Euphriam and Ebben Dorsey Quintet will perform in the park.

“They are high school students that are considered just amazing,” Raimond said of the quintet.

Aside from the high-profile headliner in McBride, the festival will celebrate 25 years by having a “Chestertown Revue,” where eight previous performers will come back and perform a 12 -minute set.

“It’s going to be almost like this choreographed thing of this amazing group,” Raimond said. “That’s much different than what we’ve done before.”

The eight performers include Durham, Matthews, Stef Scaggiari, Marlon Saunders, Lena Seikaly, Sherry Winston, Giacomo Gates and the Uptown Vocal Jazz Quartet. The revue will start at 2 p.m.

At 4:30 p.m., headliner McBride — a seven-time Grammy winner — and the New Jawn will take the stage.

“All of it is going to be exciting and it’s going to move quickly,” Raimond said of Saturday’s events.

Raimond sang praises for each of the festival’s performers and talked about her excitement to see everything being held.

Vendors will be present at Saturday’s events, selling food and beverages.

Tickets are $40 in advance or $50 at the door. Student tickets are $15 and those under 12 are free.

For more information, go to or call 410-810-2060.

The jazz festival will adhere to CDC guidelines for masks and social distancing.

Raimond said she is “delighted” to have things opened up enough to enjoy an in-person festival.

The jazz festival anchors a weekend of events in Kent County.

More than 40 local non-profit service groups will be on hand for the Kent County Volunteer Fair, according to a news release. The fair will be held from 9 a.m. to noon Saturday, Sept. 11 on High Street near the Garfield center for the Arts in downtown Chestertown.

The Galena Volunteer Fire Company will be hosting the third annual Charlie Joiner Memorial Decoy Show from 9 a.m. to 3 p.m. Sept. 11, with an auction at 1 p.m. Admission is $5.

The Chestertown Arts and Entertainment District is hosting a Fall Art Walk from 10 a.m. to 2 p.m. Sept. 11, with artists and artisans selling their works in galleries, storefronts, restaurants and pop-up venues at the Bank at 211 High St. and the Garfield Center.

The Animal Care Shelter for Kent County is inviting swimmers and their dogs to take a dip at the Kent County Community Center pool in Worton from noon to 2 p.m. Sept. 11 for a Doggie Poolooza fundraiser.

The Town of Galena will hold its annual 9/11 remembrance ceremony at 7 p.m. Sept. 11 at the firehouse.

On Sunday, Sept. 12, Kent Goes Purple, a monthlong campaign to raise awareness of opioids and substance use disorders, will hold its two featured events: a color fun run/walk and the Purple Jamboree, both in Chestertown’s Wilmer Park.

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