Windrow Estate Haunted Wine Run 5k

The Windrow Estate Haunted Wine Run 5k is a Halloween-themed running and walking event held at Windrow Estate Winery in Milton-Freewater, Oregon. Scheduled for October 5, 2025, this chip-timed 5k race offers participants scenic views of the historic vineyard and the Blue Mountains. Registration includes a super soft cotton t-shirt, a shatterproof collapsible wine glass, a wine glass-shaped finisher medal, a race bib, and a pour of wine at the finish.

The event welcomes all ages, allows walking, and offers age group awards across multiple categories. Virtual participation is also available. Dogs are not permitted, and strollers are allowed but not recommended due to uneven terrain. Visit the organization's website for the most recent information.