New England's 2026 high school football schedule features traditional rivalries, championship contenders, nationally recruited prospects and several intriguing interstate matchups.From Massachusetts powers meeting in marquee showdowns to top prep programs crossing state lines, the schedule offers plenty of games with regional significance. Here are 25 of the most compelling matchups across New England in 2026, listed in chronological order.Sept. 5: Tewksbury vs LeominsterTewksbury and Leominster will face off for the first time on opening night for Tewksbury. Both teams have had recent success over the years, and this will be a very underrated matchup to begin the season.Sept. 10: Dexter Southfield vs Buckingham Browne & NicholsDexter and BB&N will face off on opening night. Southfield captured the NEPSAC championship in both 2018 and 2021, but BB&N has 2024 New England Coach of the Year Mike Willey on their side, who was an ISL champion in 2016, 2018, and 2023.Sept. 11: Pinkerton Academy vs BedfordPinkerton and Bedford show up as the first New Hampshire matchup on the list as two Division I powerhouses. Last season, Pinkerton was 6-0 in their league while Bedford went 5-0 in league play and finished a perfect 12-0 overall.Sept. 11: Springfield Central vs St. Johns PrepSpringfield Central won two straight Division III championships in 2018 and 2019, but has since been moved up to Division I, where they captured a championship in 2021.Sept. 11: Milton Academy vs St. Sebastian'sMilton Academy has been undefeated ISL champions twice in the past seven years, with a New England Championship in 2025. St. Sebastian's captured the ISL championship in 2022, 2018, 2012, and six more times before that. Sept. 12: Brunswick vs Loomis ChaffeeAnother heavyweight clash in Connecticut as these division rivals face off against each other yet again early in the season.Sept. 12: Avon Old Farms vs Tabor AcademyTabor Academy makes another appearance on this list because of how much natural talent they have. This time they face off against Avon, who reside in Connecticut. This cross-state matchup will determine who the best of the best in New England truly are.Sept. 18: St. Johns Prep vs Central CatholicCentral Catholic will get another opportunity to test itself against one of Massachusetts' perennial powers.Sept. 19: Tabor Academy vs Williston NorthamptonThis matchup will feature plenty of Division I talent and will be a masterclass of elite high school football. From Peter Bourque to Nate Ellis, this will be a matchup that brings in a large crowd due to the sheer amount of talent on both teams.Sept: 19: Nashua vs Bishop GuertinThird-ranked Nashua takes on second-ranked Bishop Guertin in this New Hampshire rivalry early in the season. Both teams feature multiple D1 all-state members.Sept. 26: Phillips Exeter vs Cheshire AcademyExeter and Cheshire Academy will cross state borders to face off in a game loaded with Division I talent in late September. Oct. 2: King Philip vs Oliver AmesKing Philip is a four-time state champion and most recently secured a state title in 2025. The Hockomock League matchup gives defending state champion King Philip an early test against Oliver Ames.Oct. 2: Middlebury vs Hartford (VT)Hartford enters 2026 after a 9-1 season and faces a Middlebury program looking to improve on last year's 5-4 finish.Oct. 3: Phillips Exeter vs Williston NorthamptonAfter last season, Exeter showed it could compete with some of New England's top prep programs. Dexter Southfield and highly recruited Jeremiah Figaro face one of their biggest tests of the season against Avon Old Farms.Oct. 10: Avon Old Farms vs Choate Rosemary HallLast season, Choate finished their season with an 8-2 record, playing against some of the top teams in the area. They lost to Avon 14-13 last season and will look to reverse the result in 2026.Oct. 16:. Catholic Memorial vs Xaverian BrothersCatholic Memorial and Xaverian are no strangers to each other. The longtime Massachusetts rivals meet again in one of the state's most anticipated regular-season matchups.Oct. 17: Brunswick vs Cheshire AcademyCheshire Academy has enjoyed considerable NEPSAC success, winning championships in 2016, 2023 and 2025. However, Brunswick has had equal success, with championships in 2022, 2019, and 2015.Oct. 17: St. Thomas More vs IMG AcademyAlthough IMG Academy is from Florida, we couldn't help but mention this game between St. Thomas More of Connecticut and the nationally ranked powerhouse IMG. The matchup gives St. Thomas More a rare opportunity to measure itself against IMG Academy, one of the nation's most prominent high school football programs.Oct. 24: Thornton Academy vs Bonny EagleTwo of Maine's most accomplished football programs meet in late October. Thornton is a 38-time state champion, while Bonny Eagle has captured seven Class A Maine State championships since 2000, with multiple undefeated seasons. Oct. 30: St. Johns Prep vs Catholic MemorialWith Halloween on the horizon, this is a scary matchup. Five-star quarterback Christopher Vargas takes on one of the nation's best in a must-see matchup. Prep is a 9-time Division I state champion taking on a known rival.Oct. 30: Dexter Southfield vs Avon Old FarmsDexter Southfield and Jeremiah Figaro will face their toughest test in late October. Figaro holds over 30 Division I offers and will see if his impact is enough to take down Avon. Nov. 7: Loomis Chaffee vs Avon Old FarmsThis matchup is intriguing Connecticut prep matchup, with both teams constantly fighting for bragging rights. Although Loomis only went 3-6 last season, they look better than ever heading into next season.Nov. 14: Tabor Academy vs Buckingham Browne & NicholsBoth teams yet again feature so much talent that we couldn't resist putting this game on here.Nov. 14: Exeter vs AndoverThis is the 145th renewal of this matchup, a sheer tradition that forces its way onto the list like no other in New England. Nov. 26: St. Johns Prep vs Xaverian BrothersAnother classic Thanksgiving matchup here in New England. St. John's Prep has gotten the better of Xaverian in recent meetings, but Xaverian still has four more state championshipsAdd us as a preferred source on GoogleFollow