Chestertown's five generations of barbers By MAEGAN CLEARWOOD Student intern | Posted: Thursday, June 7, 2012 1:00 am CHESTERTOWN More than 50 years after its construction, the College Heights Barbershop no longer boasts a laundromat or coinoperated televisions. It does, however, offer one amenity most customers can't find anywhere else: A family legacy. Drew Thompson, 20, marks the fifth generation of barbers in the Thompson line, following the footsteps of his father, grandfather, greatuncle, great grandfather and greatgreatgrandfather. There are now three Thompsons seating customers in the family owned and operated Chestertown barbershop: Drew, his father John, 43, and his grandfather, Carroll, 66. "When John and Drew were growing up, I knew they had the skills and the mannerisms if they wanted to be barbers," Carroll said. With curtains drawn and registers closed, grandfather, dad and son settled down in their three barber chairs to recount the Thompson family history during an interview last week. They didn't look like they were closing shop after a long day at work – they looked like they were at home.
Barbers of Chestertown Three generations of the Thompson family are working together at the College Heights Barber Shop in Chestertown. From left are John Thompson, Carroll Thompson and Drew Thompson.
All three generations grew up in and around barbershops, starting with Carroll, who spent many of his afterschool hours in his family's business in Rock Hall. He learned to cut hair from his grandfather, Jewell Thompson, and earned his apprenticeship license at 15. Although barbering was in his blood, Carroll decided "I'd better know what I'm doing," headed to Wilmington, Del., and became the first in his family to attend barbering school. "I knew I wanted to be a barber from being around the shops. I was raised in them," he said. "I always wanted to do that." Carroll's uncle, Paul Thompson, built College Heights Barbershop in 1959, and as soon as Carroll was ready, he joined him in the front room. "My uncle told me, 'I have a chair for you,'" Carroll said. John's calling wasn't as instinctive as it was for his father. His first vocational goal was masonry, but after attending school, he had second thoughts and attended barbering school in Baltimore. "I saw what Dad was doing. It was an instant job, and a possible business down the road," he said. Carroll never pressured John to continue in the family business, but was happy to teach his son all the tricks of the trade. "I knew that he could do it," he said. ""There's a lot of other things out there, but he has the opportunity for advancement here." Drew's call to barbering also took some trial and error. He attended college for a semester after graduating from high school, but quickly realized that it wasn't for him. He transferred to his father's alma mater in Baltimore, and despite the long hours and exhausting commute, Drew learned to love