Middletown
Bears • Class AA • Division 1
Program Overview
Middletown enters 2026 after reaching the 2025 Section IX Class AA championship game and earning an at-large berth in the NYSPHSAA tournament. The Bears remain one half of the historic Erie Bell rivalry with Port Jervis.
Program Information
Program
Middletown
Division
Division 1
County
Orange County
Enrollment
2,085
Home Field
Middletown High School
Playing Format
11-Man
Head Coach
Tim Strenfel
2026 Schedule
| Week | Date | Site | Opponent | Time | Venue | Status |
|---|---|---|---|---|---|---|
| Week 0 | Fri, Sep 4 | Home | Arlington | TBD | Middletown High School | Scheduled |
| Week 1 | Thu, Sep 10 | Away | Cornwall | 7:00 PM | Cornwall Central High School | Scheduled |
| Week 2 | Sat, Sep 19 | Away | Minisink Valley | 7:00 PM | Minisink Valley High School | Scheduled |
| Week 3 | Sat, Sep 26 | Home | Port Jervis | 1:00 PM | Middletown High School | Scheduled |
| Week 4 | Fri, Oct 2 | Away | Pine Bush | 6:00 PM | Pine Bush High School | Scheduled |
| Week 5 | Fri, Oct 9 | Home | Valley Central | 6:00 PM | Middletown High School | Scheduled |
| Week 6 | Fri, Oct 16 | Home | Newburgh Free Academy | 6:00 PM | Middletown High School | Scheduled |
| Week 7 | Fri, Oct 23 | Home | Monroe-Woodbury | 6:00 PM | Middletown High School | Scheduled |
| Week 8 | Fri, Oct 30 | Away | Kingston | 7:00 PM | Dietz Stadium | Scheduled |
Program History
Section IX Championships
1993 Section IX Class A Champion 1994 Section IX Class A Champion Spring 2021 Section IX Class AA Champion 2023 Section IX Class AA Champion
Rivalries and Key Opponents
Port Jervis — Erie Bell rivalry
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