According to Harwich Police, tree work was being done on Round Cove Road when the accident occurred just before 2:30 p.m.
Harwich Fire and Rescue crews rushed the man to Barnstable Municipal Airport in Hyannis where they met a Medflight crew.
The Medflight helicopter flew the victim to Beth Israel Deaconess Medical Center in Boston.
Fire officials would not comment on the extent of the injuries suffered.
The incident is still under investigation.