Healdsburg is an incredible vacation destination any time of year, but the area truly comes alive in the fall. There are fall events in Healdsburg almost every day of the season, so there’s always something new for you and your family to discover. You can mingle with the locals and get a special dose of culture in these fun events, which are all just minutes from our Wine Country vacation rentals. Read on for some of the best fall things to do in Healdsburg.

Healdsburg Harvest Fair Poster

Healdsburg Harvest Fair

The Healdsburg Harvest Fair has been bringing locals and visitors together for 45 years. Once you visit, it won’t be hard to see what draws the crowds and what earned Harvest Fair the title of Best Annual Festival of Healdsburg in 2015! You will experience the best farm-to-table cuisine, along with award-winning beer, wine, and spirits. One part of the Harvest Fair that you just can’t miss is the World Championship Grape Stomp. There are multiple qualifying rounds as well as the World Championship round to finish it off, and it’s simply a fun event to witness. There are also competitions in wine, food, and homebrews. This festival is a foodie’s paradise!

The Healdsburg Harvest Fair will take place on October 4th and 5th, 2019. Tickets can be purchased online or at the fairgrounds box office, located at 1350 Bennett Valley Road in Santa Rosa.

Alexander Valley Film Festival

2019 will be the 5th year for the Alexander Valley Film Festival, the perfect combination of food, film, and fun. Their blend of “independent cinema with a Hollywood flare” will be music to the movie lover’s ears, and the festival places an emphasis on socially conscious films highlighting directors of color, LGBTQ+ artists, and more. In addition to watching the films, you will get to sample from Healdsburg’s best chefs and wineries and can meet with local film students and artists. This festival presents the perfect opportunity to make unique memories and experience some incredible art.

The 2019 Alexander Valley Film Festival takes place October 17th through 20th, 2019. The majority of events will be held at the Clover Theater in Cloverdale and the Raven Film Center in Healdsburg, as well as a few other venues throughout the county. Tickets can be purchased online at avfilmsociety.org.

An image of couple running in a marathon

Healdsburg Wine Country Half Marathon

If you’re looking to get some exercise on your Wine Country vacation, register for the Healdsburg Wine Country Half Marathon. For 10 years, runners have been coming out for this race that runs through the picturesque Northern California wine region. The path will take you through hills and valleys from Geyserville through Healdsburg, and you will be right near the winery when you finish for a special treat. As the race takes place near Halloween, runners in costume are always welcome!

The Healdsburg Wine Country Half Marathon will take place on October 26th, 2019 at 7:30 a.m. Registration is $110 and up. The race is limited to 2,500 entrants, so be sure to register early if you want to compete. Please note that the half-marathon only allows 3 hours and 30 minutes to finish, which equals a pace of 16 minutes per mile or faster. If you are unable to meet this time, it is recommended that you do not register.

This is just a handful of the fun fall events in Healdsburg, but there is plenty more to see and do while you’re in town. Fall is an incredible time in Wine Country, and we can’t wait to help you plan your dream vacation here. For more information on our Healdsburg vacation rentals, contact us today!

Healdsburg Property Management manages single-family homes, duplexes, four-plexes and multi-unit properties of up to seven units throughout Sonoma County’s Wine Country, including Healdsburg, Windsor, Northern Santa Rosa, Cloverdale and Forestville.