James M. Bennett High School is currently in the funding stages for a replacement building. Construction is slated to start in 2008, with a goal completion date of 2011. The new building will include state of the art technology, including geothermal heating control, and up-to-date educational tools such as LCD projectors, digital white boards, and document cameras replacing the current overhead projectors and chalkboards.
JMB's Destination ImagiNation creative problem-solving teams have success in recent years. Two teams qualified for travel to Global Finals in 2003 (one state-champion, one runner-up) In 2007, a team of freshmen won the state championship and traveled to the University of Tennessee in Knoxville for the Global Finals tournament.
The school's Academic Challenge team has also fared well in recent years, placing in the top three in the Comcast Academic Challenge for four straight years, and appearing on WJZ-TV's high school quiz show It's Academic.
Current Advanced Placement offerings at James M. Bennett include Biology, Chemistry, Environmental Science, English Language and Composition, English Literature, U.S. Government and Politics, United States History, European History, Calculus, Spanish, and Latin.
The school's faculty and staff have won numerous awards in recent years. In 2004, Patricia Adkins was named the Maryland's Vice-Principal of the Year. Brian Raygor was the 2004-05 Wicomico County Teacher of the Year, and recipient of the National Association of Biology Teacher's Outstanding Biology Teacher Award. Biology teacher Jeff Royer was recognized as being Technology Educator of the Year in 2004. Raygor, Cheryl Doughty (Family and Consumer Science), Don Abbatiello (Social Studies) and Lisa Santore (English Language Learners) have earned National Teacher Certification from the National Board for Professional Teaching Standards (NBPTS). Doughty was also recognized as a "Service Learning Fellow" for her innovative student service learning projects and webpage. Wal-Mart Teacher of the Year recipients include social studies teacher Josh McKelvy and English teacher Mary Lou Coffin.
James Bennett High School's enrollment has been steadily increasing over the past 12 years. The enrollment peaked in 2005 at 1,388.