Football fans in Connecticut have barely had time to catch their breath since the state’s high school season wrapped up in mid-December, but the action never really stops. With the Connecticut High School Football Alliance unveiling its largest-ever slate of games for the 2026 season, anticipation is already building across communities and locker rooms statewide. The Alliance’s 2026 schedule, announced last week, features a record-breaking 122 matchups, marking a significant milestone as every conference in the state has agreed to participate for the first time since the Alliance began scheduling out-of-conference games in 2017.
For die-hard football enthusiasts, the offseason is just a technicality. As coaching changes and schedule releases keep the rumor mill spinning, this year’s Alliance schedule is a particularly juicy topic. The move to a fully inclusive schedule is seen by many as a step toward a more unified and competitive landscape. “If you’re like me and have come to the conclusion that the conferences in football mean nothing and a statewide schedule is the future of football, then this appears to be a step in the right direction,” wrote a local columnist in a special edition of the Extra Points column.
Of course, the schedule isn’t set in stone until the CIAC’s September deadline, and playoff divisions—which play a role in some of these matchups—won’t be finalized until later this year. But that hasn’t stopped fans and pundits from poring over the list and debating which games will define the 2026 season. The Alliance’s matchups have been ranked into several tiers, including “Must See” and “Intriguing,” with a few less-anticipated games rounding out the bottom of the list.
At the very top is a clash that’s sure to draw attention: Fairfield Prep at New Canaan in Week 2. These two perennial powerhouses are regular fixtures in the GameTimeCT Top 10 poll, and both have plenty to prove. New Canaan comes into 2026 riding high after four straight state championships, while Fairfield Prep is still chasing its first title since 1988. “A win for either would go a long way to defining their season,” the column noted, highlighting the game’s potential to set the tone for the fall.
Not far behind in the rankings is Killingly at Sheehan in Week 1—a matchup that pits two small-school juggernauts against each other. Both programs have championship pedigrees, with Killingly taking the Class SS title two years ago and Sheehan making deep playoff runs. “These two programs don’t rebuild, they reload and find themselves in championship contention every year,” the writer observed. The intrigue is only heightened by recent playoff history between the teams, and the fact that whenever Killingly ventures outside its conference, fans take notice.
Week 2 also features Windsor at St. Joseph, another heavyweight battle between recent state champions. Windsor captured the Class L crown last year, while St. Joseph won Class M the year before. The two last faced off in 2021, splitting their meetings between the regular season and the Class L semifinals. “You know I will be there,” the columnist quipped, underlining the game’s must-watch status.
Berlin at Wilton in Week 2 promises to be a fascinating matchup as well. The defending Class M champion Redcoats will face a Wilton squad that has been knocking on the door in recent years. Both teams are dealing with significant graduation losses, adding an extra layer of unpredictability to the contest. “Heavy graduation on both sides adds to the intrigue,” the preview noted, suggesting that new stars could emerge under the Friday night lights.
Southington at Newtown rounds out the top five, with the Blue Knights looking to build on a surprise run to last year’s championship game. Newtown, which last claimed a state title in 2019, is always a threat, even if recent postseason success has eluded them. The matchup is expected to be a litmus test for both programs as they seek to establish themselves early in the season.
Other notable games include Killingly at North Haven in Week 11—a battle between two teams known for their ground-and-pound running attacks. North Haven, which has claimed two state titles in four seasons, faces a Killingly squad that has reached the Class SS final in consecutive years. “This game should be over in an hour of real time,” joked the columnist, referencing both teams’ penchant for keeping the clock moving.
The Alliance has also expanded its reach by including out-of-state opponents, such as Bishop Hendricken of Rhode Island, who will face Hand in Week 1. The Hawks have made three trips to Connecticut in the past two seasons but have yet to notch a win. This matchup will serve as an early barometer for Hand, the defending Class SS champs, as they look to reload after graduating a strong senior class.
Several games offer redemption opportunities for teams looking to rebound from disappointing playoff exits or to build on recent success. Greenwich at New Britain in Week 2 is one such example. New Britain, after a frustrating first-round loss as the No. 1 seed in last year’s Class LL tournament, is eager to prove itself against a Greenwich team aiming for a third straight LL title. “New Britain and its fans have been clamoring for respect across the state; the first round loss to NFA did not help,” the article pointed out.
Wilton at Southington in Week 4 and Guilford at Rockville in Week 2 are among the other matchups that pit programs from different playoff classes against each other, providing valuable tests and potential playoff previews. The Alliance’s commitment to creating competitive, cross-conference matchups is evident throughout the schedule, with longtime rivalries, emerging contenders, and intriguing first-time meetings all in the mix.
With 122 games on the docket, the 2026 Connecticut High School Football Alliance schedule offers something for every fan. While there’s still some uncertainty regarding final playoff divisions and possible late changes, one thing is clear: the fall football season promises to be as unpredictable and exciting as ever. As the countdown to kickoff begins, coaches, players, and communities across the state are already circling dates on their calendars and dreaming of championship glory.
The Alliance’s record-setting schedule and full conference participation signal a new era for Connecticut high school football—one where statewide competition and cross-conference rivalries take center stage. Stay tuned, because when September arrives, the action will be nonstop, and every Friday night will bring another story worth telling.