Sat, Sep 26, 2026

Bayside Five and Wine

Bayside, WI

Registration openAnnual since at least 2021

Entry is $30 now and rises to $40 after Aug 22, 2026, so registering before then saves $10.

About the Bayside Five and Wine

The race starts at a street intersection in the village and winds through the surrounding neighborhood. There are several distance options, including a timed run and a walk, and one of the walk options lets you carry a glass of wine along the route, with a second pour available at a checkpoint midway. Strollers and dogs are welcome on course.

After finishing, the gathering continues at a picnic area with a beer garden and an outdoor movie screening on a nearby hill. The post-race setup is part of a broader fall festival, so there is more going on around the finish than a typical race wrap-up.

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Finish-Time Stats

Going by the 2025 results, this is a small, friendly field, with a competitive front end and a big recreational middle.

· 2025 results

29finishers

19:28winner

30:21median

43:35cutoff

Top 3: Matthew Krzemienski (19:28) · A. Jensen (20:44) · Michael Olson (21:51)

The Bayside Five and Wine has been held every year since at least 2021. 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 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

5K Run9/26/2026 16:00$30

2-Mile Walk9/26/2026 16:00$30

2-Mile Wine Walk9/26/2026 16:00$30

4-Pack9/26/2026 16:00$110

Plan Your Trip

Where to Stay

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Common Questions About the Bayside Five and Wine

Will I finish last at the Bayside Five and Wine?

Almost certainly not. Half the race field finished slower than 30:21, and the last recorded finisher came in around 43:35, so there is a long tail of runners behind the middle of the pack. Most fields are far slower than people expect.

Is the Bayside Five and Wine a good first race?

It is a small race (29 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 race, that spread matters more than the winner's time.

How competitive is the Bayside Five and Wine?

The race winner ran 19:28 while the median finisher took 30:21. That spread points to a mixed field, with a competitive front and a big recreational middle.