Gardiner’s Owen Chadwick, left, celebrates with teammates Asher Nagy (12) and Trevor Baron after scoring touchdown against Messalonskee in September 2024. (Anna Chadwick/Staff Photographer)

Cony at Messalonskee, Friday: The Pine Tree Conference season begins with a matchup of two teams that expect to be playing deep into November. In Cony’s Parker Morin and Messalonskee’s Tatum Doucette, both seniors and three-year starters, this game will feature two of the best quarterbacks in the state.

Oak Hill at Winthrop, Friday: The Ramblers’ Class D South semifinal win over the Raiders in 2023 came on a last-second field goal. In last year’s regular-season rematch, all that separated the two in Winthrop’s 22-21 victory was a missed extra point. With both teams among the best in D South again this fall, another tight battle is likely.

Freeport at Winslow, Sept. 20: Hot September Saturdays mean home-field advantage for Winslow, the favorite in Class D North. Freeport, meanwhile, is a team other D South coaches see as a top contender. Winslow’s Hassan Hobbi and Freeport’s Liam Emmons are also among the state’s best kickers, which could be a factor in a tight game.

Lawrence at Fryeburg Academy, Oct. 10: Although Lawrence must replace its key players at the skill positions, the Bulldogs return most of their contributors in the trenches. It will be interesting to see John Hersom’s crew fares against a Raiders team that’s new to Class B South after winning the Class C state championship last year.

Gardiner at Cony, Oct. 24: No list of football games to watch in central Maine could possibly be complete without the Tigers vs. the Rams. Even as Gardiner has gone from Class B North to the statewide Class C in 2025, the two rivals will still meet in the regular season this year as they face off for the boot for the 147th time at Fuller Field.