Bayside Five and Wine 2026 — Bayside, WI

Date
September 26, 2026
Location
Bayside, WI
Venue
9075 N Regent Rd
Start Time
4:00 PM
Entry Fee
$30.00 – $145.00
Events
5K Run, 2-Mile Walk, 2-Mile Wine Walk, 4-Pack
Includes
T-Shirt & Race Day Bag | T-Shirt
Register NowRegistration Open
Join the Village of Bayside for an afternoon stroll during our Fall Fest on Saturday, September 26, 2026, starting promptly at 4pm! The start line is at the intersection of Regent Rd and Ellsworth Ln. The race winds through the beautiful Village of Bayside. Wondering which event to do?! We have plenty of options! 5k Run: A timed race for the running enthusiasts and will receive a post-race beverage. 2-mile Wine Walk: Drink while you walk. Fill up your glass at the start of the race and redeem your ticket for the second glass at the 1-mile check point or at the end of the race. You will be provided a Bayside Five and Wine glass at the beginning of the race! 2-mile walk: This will be the same route as the wine walk, just without the wine. Register individually or save money and register as a group of 4 for either the walk or run! All early bird registrations are guaranteed to receive a race shirt in requested size and race bag! Early bird promo ends August 21 so don't delay in registerin

Hotels Near This Race

Find accommodation close to the start line in Bayside, WI. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.

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Bayside Five and Wine 2026 — Bayside, WI

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Race Travel Insurance

Don't forget travel insurance for September 26.

You've trained for months and booked a trip to Bayside, WI. A pre-race injury, a delayed flight, or a family emergency can derail the whole thing. Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it, and may cover medical costs if something goes wrong on the course. Plans typically only run 5-7% of your total trip cost — and running events are covered under standard plans with no additional coverage needed.

  • Trip cancellation up to 100% of prepaid costs
  • Running events covered under standard plans — no add-ons needed
  • Trip interruption up to 150% of non-refundable costs
  • Emergency medical up to $250,000
  • Cancel For Any Reason add-on available
  • 24/7 real-time support

Affiliate links — we may earn a commission at no cost to you. Coverage terms vary by state and plan. Review policy details before purchase.