Sun, Apr 4, 2027

Trailbreaker

Waukesha, WI

Registration openAnnual since at least 2019
Marathon20 MilesHalf Marathon10K5K1.85 Miles

Entry is $32.50 now and rises to $35 after Dec 7, 2026, so registering before then saves $2.50.

Register

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.

Free race emails

Get the Weekly RunSesh

In for this one or still deciding, keep race season near Waukesha on your radar: a Monday look ahead and a Thursday rundown of the weekend's races.

Two helpful emails per week. No spam. Unsubscribe anytime.

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.

Where Would You Finish?

Enter a finish time to see where it lands against the most recent 13.1 Miles results.

Median

See how your time stacks up nationally →

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

Going for a Time?

Set a goal and get a pace band: every mile split on a card sized for your phone lock screen, so race morning needs no math.

Plan Your Trip

Where to Stay

Traveling for this race? The map shows hotels and rentals in and around Waukesha — pan or zoom to compare what's nearby.

The map is provided by Stay22. If you book through it, RunSesh may earn a commission at no extra cost to you — it never affects the races we list.

Common Questions About the Trailbreaker

Will I finish last at the Trailbreaker?

Almost certainly not. Half the 13.1 Miles field finished slower than 2:10:22, and the last recorded finisher came in around 3:50:52, so there is a long tail of runners behind the middle of the pack. Most fields are far slower than people expect.

Is the Trailbreaker a good first 13.1 Miles?

It is a small race (111 finishers), which is friendlier and less intimidating than a big-city event, though the field thins out. There is no qualifying time, and the finish-time spread above shows how varied the field really is. If it is your first 13.1 Miles, that spread matters more than the winner's time.

How competitive is the Trailbreaker?

The 13.1 Miles winner ran 1:26:53 while the median finisher took 2:10:22. That spread points to a mixed field, with a competitive front and a big recreational middle.

Share Your Card

We made you a ready-to-post image. Story fits Instagram and TikTok Stories; Post fits the feed. Download it, post it, and tag @runsesh so we can cheer you on.

Preview of your share card