2026 Williamsburg Winery 5k/10k

Prepare for an unforgettable race experience at the 2026 Williamsburg Winery 5k/10k, set amidst the picturesque vineyards of Williamsburg, VA, on May 9, 2026. This unique event invites runners and walkers alike to explore the scenic routes of the historic Williamsburg Winery property. The course offers a cross-country style run with no major hills, providing an enjoyable challenge for all ability levels while allowing participants to soak in the beautiful surroundings.

Beyond the stunning scenery, this Bishop's Events race holds a special purpose, benefiting Vet First Inc., a non-profit dedicated to employing Veterans to grow sustainable food for those in need. Twenty-five percent of all profits directly support Vet First's mission. Participants in either the 5K or 10K will be rewarded with a finisher's medal, a technical (Dri-fit) event shirt, and, fittingly, a complimentary glass of wine from the Williamsburg Winery to celebrate their accomplishment. Typical race day conditions in early May feature pleasant highs around 76°F and lows around 56°F, with only a 17% chance of precipitation, creating ideal running weather.

Whether you're aiming for a personal best or simply wish to enjoy a spirited walk through a beautiful vineyard, the 2026 Williamsburg Winery 5k/10k promises a memorable day. The chip-timed event culminates in a festive atmosphere where you can relax with a post-race drink at Wedmore Place, reflecting on your achievement and the scenic beauty of Virginia Wine Country.