The following 2021 Regular Season and Playoff Tournament awards were either achieved and/or voted on by league managers:

Frank McCoy Award, Most Valuable Player – Jack Rich, OF, Record-Journal Expos

Mike Liappes Award, Most Valuable Pitcher – Matt Curtis, P, Vernon Orioles

Hal Lewis Award, Most Versatile Player – Evan Chamberlain, P/3B, Rainbow Graphics &

AJ Hendrickson, P/C, Record-Journal Expos

Gene Johnson Award, Regular Season Batting Champion – Jack Rich, OF, Record-Journal Expos

James Gallagher Award, Rookie of the Year – Matt Curtis, P, Vernon Orioles

Jack Repass Award, Golden Glove – Corey Plasky, IF, East Hartford Jets

Bill Chapulis Award, Home Run Title – Mike Munson, OF, Malloves Jewelers

Mark and Jane Foss Award, RBI Leader – Jack Rich, OF, Record-Journal Expos

Ralph Giansanti Sr. Award, Stolen Base Title – Christian Boudreau, IF, Hartford Colts

Rev. Thomas Campion Award, Outstanding Playoff Hitter – Chris Bogan, 1B, East Hartford Jets

Mike Abbruzzese Award, Outstanding Playoff Pitcher – Bryan Albee, P, East Hartford Jets

Jake Banks Trophy, Regular Season Champion – Jack Ceppetelli, Manager, Vernon Orioles

Jack Rose Trophy, Playoff Champion – Taylor Kosakowski, Manager, East Hartford Jets