It was a hot day in Chestertown last Saturday, but by evening the shade had cooled down High Street a bit as Chestertown turned out for live music and entertainment. It was a fitting final event for Kay MacIntosh, who steps down as executive director of Main Street Chestertown at the end of the month, bringing her six-year tenure as Chestertown’s unofficial economic development director to an end.

All afternoon MacIntosh, Main Street board members and volunteers worked to ready the newly arrived Stageline 75 mobile stage purchased by Main Street Chestertown with grants from a matching grant from the Maryland Heritage Area Authority/Stories of the Chesapeake and contributions from the Robert F. Schumann Foundation, the Town of Chestertown, and Main Street Chestertown.

The total cost was approximately $100,000 and included training for town streets department staff to move and operate the stage. Main Street Chestertown has gifted the stage to the town for use by non-profits. This has been a long-term goal for MacIntosh and a fitting closing accomplishment.

As the dinner hour approached, volunteers were helping to arrange the street barricades and placement of MacIntosh’s now famous mobile planters. MacIntosh was even out there with her watering can as the staff of the Kitchen at the Imperial set tables on High Street as al fresco dining returned for 2021, another successful Main Street Chestertown effort.

By 5:00 p.m., the jazz trio Love that Jazz had tuned up and turned up their American Song Book repertoire with Al Martinez on keyboard, Tom Anthony on electric bass, and Ray Antony on drums. The trio played through the early evening, serenading street-level diners from the second-floor hotel balcony.

At 7:00 p.m., action turned to the new portable stage up High Street. Mayor Dave Foster and Main Street Chestertown board president Paul Heckles did the ribbon-cutting honors at the stage’s debut.

The ribbon cutting was followed by well-deserved public recognition for MacIntosh. Ward 2 Councilman Tom Herz, whose district includes the A&E District, read a proclamation from the Mayor & Council naming June 5, 2021 “Kay MacIntosh Day” and recognized MacIntosh’s achievements. Herz also presented her with a key to the town. Main Street Chestertown president Heckles presented a designer necklace from Create. Downtown Chestertown Association treasurer Bob Ramsey presented her a panoramic photograph of the Chestertown waterfront.

Main Street Chestertown is part of the Main Street America program, a subsidiary of the National Trust for Historic Preservation organized to promote thriving downtowns. The Main Street Chestertown program is led by a volunteer board of local business and community leaders. Over the past six years, MacIntosh and the Main Street Chestertown board have led an effort to revitalize downtown.

MacIntosh spearheaded the effort to certify Chestertown’s Arts & Entertainment District. That was successfully achieved in 2015. The A&E District encompasses much of the historic downtown district from the Chester River to Mill Street. The A&E District provides state tax incentives to promote art created and sold in the district, as well as property tax credits for property renovations for arts-related purposes.

MacIntosh developed the popular “Dickens of a Christmas” that debuted in December 2017, transforming an otherwise quiet High Street into 19th century holiday London. MacIntosh was well into planning Dickens 2020 when COVID-19 brought that to a halt.

MacIntosh also helped to promote Main Street’s Facade Improvement Program that offers matching grants for façade improvements made to commercial buildings and storefronts in the historic downtown district.

During the COVID-19 pandemic, MacIntosh became a consistent voice of encouragement for downtown businesses trying to stay afloat, starting regular zoom calls, connecting businesses and resources, and even continuing an effort to connect local retailers with a business consultant.

When asked about her favorite Main Street accomplishments, MacIntosh reflected, “For the Town, I think my favorite was the Dickens weekend — working with co-chairs Kathleen King and Ellen Hurst and many key volunteers and seeing the community embrace it. That first Friday night with the fire-dancers, seeing the looks on the faces of children was so priceless.”

“Second would be those rolling planters and the street dinners they helped define,” MacIntosh continued. “Those projects really brought people together during the early days of the pandemic. So many volunteers helped build and fill the planters, and then showed up to roll them up and back from the marina as needed.”

“And third, was watching Jon and Barbara Slocum create Cars on High and the first Chestertown Car Show (2019). Who knew there were so many ‘car people?’,” MacIntosh said.

Missing from the event, but not forgotten, was MacIntosh’s husband and chief volunteer Bill MacIntosh, who has clocked thousands of volunteer hours supporting his wife’s work.

After the accolades came entertainment from Best Kept Soul with its mix of Soul, Motown and R&B hits. The music brought out the public onto the dance floor. Fun was definitely had by all who attended.
Many thanks, Kay!