Chestertown High Street retail legend Anna E. Scott Cole of Scottie’s Shoe Store and Newsstand fame died on Sunday, June 14, 2020 at Corsica Hills Nursing Home in Centreville after an illness. She was 92-years-old.

Anna Scott Cole (in red at center) is honored in 2013 by members of the Chestertown Mayor & Council for four decades in business on High Street. Photo by Daniel Menefee

Miss Anna was born on April 12, 1928 in Worton, MD. She was the daughter of the late Merritt and Lulu Meekins. On October 4, 1948, she married Earl F. Scott. They made their home in Hanesville, near Worton. The Scotts enjoyed spoiling their nieces and nephews, however, they did not have children of their own. Earl passed away suddenly in 1982.

Anna began 65-year career on High Street at Fox’s Five and Dime. In 1973, she ventured out on her own by purchasing Scottie’s Shore Store. Scottie’s was a place where you could purchase steel toe work boots, custom dyed wedding shoes, baby’s first walking shoes and penny candy.

In 1992, fire transformed the 300 block of High Street when McCrory’s (formerly Fox’s) and the Chestertown Newsstand (formerly Fox’s Family Shoes where Anna got her start), burned down. That cleared the way for the Alexander Building.

As the High Street retail world changed, Scottie’s went through changes as well. Anna expanded to carry newspapers, magazines and came to meet her second husband, Howard M. Cole. Together they sold, delivered, and reserved papers until Howard’s untimely death in 1995. Anna would continue to be the town’s newsstand until her retirement in 2013.

It was noted that Anna never met a stranger and had the privilege of meeting and serving many. She held court every morning before 7 a.m. where her daily visitors drank coffee, read their newspapers, and chatted. Anna was known for dispensing advice, discussing current events and gossiping daily about local happenings. At some point in the day she would be joined by her best friend, Ruth Briscoe. The two are reunited again.

In the video below, Anna is honored in 2013 for her “public service” to Chestertown in a quiet gathering of long-time friends. who chatted and told stories of Anna’s contributions to the town.

Anna closed Scottie’s Shoe Store and Newsstand in May of 2013 — after 39 years in business on High Street.

“You provided a place for people to come and get their papers everyday…a place for people to gather and talk,” Then Chestertown Mayor Margo Bailey told Anna at a quiet party at Scottie’s on May 24, 2013 that began Anna’s retirement.

On that day Bailey presented Anna with a key to the city for her 65 years on High Street, which started with her first job at Fox’s Five and Dime Store — to opening Scottie’s Shoe Store and Newsstand in 1973.

“You went through some trying times,” Bailey told Miss Anna at the time. “But you always prevailed because of your steadiness of character and personality. This town will always be indebted to you for what you’ve given to us.”

In May, 2014, she was honored by the Chestertown Tea Party Festival Committee with the Edna Ross Award for her commitment to downtown business.

Anna is survived by two sisters, Blanche E. Scott of Worton and Edith F. Hurtt of Worton. She is also survived by many cherished nieces and nephews. She was preceded in death by her siblings, Cary Rebecca Gary, William H. Greenwood and George A. Meekins.

Graveside services will be held on Friday, June 19, 2020 at 11:00 in Still Pond Cemetery. Contributions may be made to Still Pond United Methodist Church, P.O. Box 1, Worton, MD 21678.

Arrangements by Fellow, Helfenbein & Newnam Funeral Home.