#20 Winchester
Coming at #20 on our list is a team that was not in our rankings last year. The Winchester Red and Black return their entire top seven from the 2025 season in which they finished fourth at the competitive Middlesex League Championships. Their top seven all ran 17:30 or faster, and their top four ran 16:34 or faster at that meet. While that course at the Woburn Country Club is notoriously fast (and short), there is still plenty reason for excitement this fall.
Senior Noah Damaske was their top runner all last season, finishing 11th at ML-12s. While he’ll look to lead and set the standard for the deep group of returning runners, he should have plenty of company at the front of the pack. Returning Sophomores Tyler Bernstein and Noah Mannelli backed up strong Cross-Country seasons with fast times on the track. Mannelli ran 9:46 for Two Miles and Bernstein ran 9:50.
We know Winchester will be well represented up front, but like most teams, their success will be defined by their depth. Athletes like Nate Bickford, Adel Halaseh (17:10), and Callum Knowles (17:31) can make big leaps this fall. If they can duplicate their times on more challenging courses like Wrentham or even Fort Devins, they’ll have Winchester in a great position. Nikola Dimitrov may be their wild care this season. The senior skipped indoors last season and then focused on shorter distance outdoors. What will he bring to the table this fall? Keep an eye on the Red and Black this season. They debut against Melrose on 9/10.
Projected Top 5 (Times Via Athletic.net)
Noah Damaske 15:51
Tyler Bernstein 16:02
Noah Manneli 16:28
Nikola Dimitrov 16:34
Nate Bickford 17:01
