Congratulations to Ravens fans on last week’s victory over the Cleveland Browns. For this week’s Flashback Photo, an earlier football team takes the field. The 1921 Chestertown High School squad in this image looks like a daunting opponent. With their steely gazes and bulky padding under their jerseys, they surely must have intimidated all their rivals. Image courtesy of the Historical Society of Kent County. 

If you have local team photos from other years that you’d like to share, please send them to [email protected].

Fred Bonnett Image Courtesy of Jan Bonnett Gavin. 

We’re flashing back to the 50s this week. In this January 1957 photograph, Fred Bonnett of Chestertown is celebrating his bar mitzvah, the Jewish ceremony marking a 13 year old’s coming-of-age. Bonnett’s  Department Store, founded by Fred’s grandparents Benjamin L. Bonnett and Yetta Dahne Bonnett, was a mainstay of Chestertown’s business district for much of the 20th century. An ad in the Chestertown Transcript of May 2, 1925 boasts of “a complete line of Ladies Suits and Spring Coats, Men’s and Boys’ Suits and Coats, Men’s and Boys’ under Garments, Ladies’, Men’s and Boys’ Shoes” and “Bed spreads, sheetings and many other useful articles”

Stories from the Bonnett family’s experience in Kent County will be featured along with other families’ stories in the Historical Society’s upcoming exhibit, On New Shores: A History of Jewish Lives in Kent County. An reception celebrating the exhibit opening will be held from 5 -7 p.m. on October 3 at the Bordley History Center, followed by two more events that weekend. At 2 p.m. on Saturday, October 4, Susan Hollins will present a piano concert, Jewish Composers of the Immigration Era, at Emmanuel Episcopal Church, and on Sunday, October 5, a panel discussion about the exhibit and related topics will take place at Kent Cultural Alliance at 2 p.m. All are welcome! Image Courtesy of Jan Bonnett Gavin. 

Image courtesy of Historical Society of Kent County.

This undated photo of downtown Massey, Maryland from the turn of the 20th century reveals a peaceful downtown with early automobiles on a still-unpaved central thoroughfare, towering trees, and classic Eastern Shore woodframe buildings.

Zoom in to find details that are hard to discern, like two white-clad figures standing in front of the post office. Another, in the center of the frame but almost undetectable and even more ghostly, is standing in or perhaps crossing the street. This form, possibly a young boy caught in motion and blurred in the long exposure needed for photographs of the era, manages to bring the image to life more acutely despite being so hard to make out, perhaps because he is so clearly an unposed and unintended subject.

Share your memories of Massey in the comments below or by emailing [email protected].

Chestertown is once again enjoying a fresh injection of youth and enthusiasm as new students at Washington College get settled and explore their new environs. In honor of the scholars who will be spending the next few years with us (at least!), today’s Flashback Photo depicts the Washington College Class of 1895. This group is significant because it includes Miss May Matthews, the first woman to complete the course at Washington College. Her forthright gaze, directly into the camera’s lens is in notable contrast with her classmates’, suggesting a straightforward manner and an admirable confidence that may have stood her in good stead as a Washington College trailblazer. New students in 2025 may feel understandably nervous as they begin their higher educational journey, but no doubt they will soon be boldly blazing trails of their own in various ways. Image courtesy of the Historical Society of Kent County.

 In honor of this weekend’s Legacy Day celebration, today’s Flashback Photo is from Butlertown. In this 1970 image, the pastor and members of the congregation stand in front of Mount Olive Church in Butlertown, Worton, Kent County. Butlertown is just one of the locations featured in this year’s Legacy Day exhibit, now on view at the Bordley History Center. The theme of this year’s festival is Historic Black Communities, the many enclaves of Black family and cultural life that have dotted the Kent County landscape for over 150 years.

All are invited to visit and view the exhibit, co-curated by Bill Leary and Vanessa Ringgold, and featuring photographs, text, and maps. The Bordley History Center at 301 High Street in Chestertown will be open extended hours for Legacy Day weekend, until 4 p.m. on Friday, August 15, and until at least 4 p.m. on Saturday, August 16. Image courtesy of Historical Society of Kent County and Chesapeake Heartland.

As the months with “R” in their names and the unofficially official oyster-eating season inches closer on the calendar, in today’s Flashback Photo, a classic Chesapeake Bay oyster buyboat turning 100 years old this year, the Nellie Crockett. Built in 1925 in Crisfield for “Shad” Crockett of Tangier, Virginia and named for his daughter Nellie, she served as a buyboat until 1990, except during World War II, when she was a fire boat for the US War Shipping Administration from 1942 to 1945. Today, the Nellie Crockett is a National Historic Landmark whose home port is in Kent County, on the Sassafras River. Image courtesy of Historical Society of Kent County.

This week, we share an image from the new Legacy Day exhibit, now on view at the Bordley History Center. In keeping with the theme of Legacy Day 2025, Historic Black Communities of Kent County, this photograph, dated 1963, shows the Somerville family, with mom Kay and three children beautifully dressed and standing in front of a pale blue and white car.

To see more photos and learn about the many significant communities in Kent County that have been a locus of Black life and society throughout the county’s history, visit the Historical Society tonight between 5 and 7 p.m. for First Friday, or any time in August and September. Image courtesy of Historical Society of Kent County.

In honor of the 2025 Kent County Fair currently underway, a Flashback Photo of a much earlier fair. Although the digital image of this photo has been adjusted to make it easier to see, you still have to study it carefully to see the details. Zooming in will help.

In the undated photo, the Kent County Fair looks much different from the 21st century version of the event, but horses, onlookers, and even in an image lacking the clarity and color of the photos we take today, a sense of excitement and occasion comes through.

To all this year’s fairgoers and participants, have fun, good luck, and enjoy the BBQ! Image courtesy of the Historical Society of Kent County.