About the Trailbreaker
The Trailbreaker runs through Waukesha each spring, with distance options stretching from a short road run up to a full marathon. The course moves through city streets and park corridors, and the whole event exists as a fundraiser for local parks, trails, and the urban forest. Volunteers staff the whole operation, which gives the morning a noticeably unpretentious feel.
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Finish-Time Stats
Going by the 2026 results, this is a small, friendly field, with a competitive front end and a big recreational middle.
13.1 Miles · 2026 results
111finishers
1:26:53winner
2:10:22median
3:50:52cutoff
Top 3: eric crutchfield (1:26:53) · Gerald Cameron (1:33:20) · Jim Cordingley-Power (1:33:53)
3.1 Miles · 2026 results
91finishers
19:17winner
34:24median
1:02:15cutoff
Top 3: Keagan Foerch (19:17) · Benjamin Hoegh (20:36) · Bennett Warp (22:44)
26.2 Miles · 2026 results
89finishers
2:47:09winner
4:17:17median
6:49:35cutoff
Top 3: Kyle Martinelli (2:47:09) · Connor Cook (2:51:13) · Carl Greene (2:54:18)
6.2 Miles · 2026 results
89finishers
41:29winner
1:02:47median
1:54:27cutoff
Top 3: Tim Donahugh (41:29) · David Hart (43:40) · Pate Lantz (44:42)
20 Miles · 2026 results
9finishers
2:28:54winner
2:58:19median
4:26:19cutoff
Top 3: Lisa Kirt (2:28:54) · Stephen Matthews (2:30:16) · Michael Ryan (2:45:12)
1.85 Miles · 2026 results
2finishers
34:05winner
45:00median
55:54cutoff
Top 3: Chery Partridge (34:05) · Therese Hansen (55:54)
The Trailbreaker has been held every year since at least 2019. That is as far back as RunSignup's records for this race go, so it may well be older.
How we calculate these stats: RunSesh calculates these figures from the most recent published results of past editions, sourced from RunSignup. We show aggregates only: field size, winning and median times, and the cutoff. We never publish individual finisher tables. Last updated Jul 27, 2026.
Distances & Start Times
26.2 Miles4/4/2027 08:00$70
20 Miles4/4/2027 08:00$70
13.1 Miles4/4/2027 08:00$50
13.1 Miles4/4/2027 08:00$50
6.2 Miles4/4/2027 08:15$33
3.1 Miles4/4/2027 08:15$33
6.2 Miles4/4/2027 08:15$33
3.1 Miles4/4/2027 08:15$33
1.85 Miles4/4/2027 08:15$33
Kiddos 1K4/4/2027 07:45Free
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