| Milford Fire & Ice Festival | Downtown Milford Green | | 2027-01-23 |
| Milford Winter Wonder Flagship 5K/10K | Milford Yacht Club | | 2027-02-07 |
| Movie: And Then There Were None (1945) w/ John DiLeo | Milford Theater | | 2026-10-17 |
| Play: Murder on the Orient Express | Milford Theater | | 2026-10-30 |
| Play: Murder on the Orient Express | Milford Theater | | 2026-10-31 |
| Play: Murder on the Orient Express | Milford Theater | | 2026-11-01 |
| Play: Murder on the Orient Express | Milford Theater | | 2026-11-06 |
| Play: Murder on the Orient Express | Milford Theater | | 2026-11-07 |
| Play: Murder on the Orient Express | Milford Theater | | 2026-11-08 |
| Musical: Irving Berlin's White Christmas | Milford Theater | | 2026-11-28 |
| Musical: Irving Berlin's White Christmas | Milford Theater | | 2026-11-29 |
| Musical: Irving Berlin's White Christmas | Milford Theater | | 2026-12-05 |
| Musical: Irving Berlin's White Christmas | Milford Theater | | 2026-12-06 |
| Musical: Irving Berlin's White Christmas | Milford Theater | | 2026-12-12 |
| Musical: Irving Berlin's White Christmas | Milford Theater | | 2026-12-13 |
| Musical: Irving Berlin's White Christmas | Milford Theater | | 2026-12-19 |
| Musical: Irving Berlin's White Christmas | Milford Theater | | 2026-12-20 |