As the days grow shorter and the leaves turn to gold in Southern Oregon, October ushers in the final month of the Shakespeare season at the Oregon Shakespeare Festival (OSF). For theater lovers, it’s a bittersweet moment—the closing act of a year filled with unforgettable performances. If you’ve ever dreamed of experiencing Ashland in autumn, now is the perfect time, and Country Willows Inn is the ideal place to stay while you enjoy it all.
What’s On Stage in October
The 2025 OSF season concludes on October 26, with several standout productions carrying the festival to its finale. Shakespeare’s Julius Caesar continues through the very last day of the season, offering a timeless exploration of politics and power. In the same theater, audiences can also enjoy Oscar Wilde’s sparkling comedy The Importance of Being Earnest, which closes on October 25.
For those who visit earlier in the month, the outdoor Allen Elizabethan Theatre hosts the lively and playful The Merry Wives of Windsor, ending October 12. October also brings the last performances of Into the Woods, a beloved musical weaving together classic fairy tales, and Quixote Nuevo, a lyrical, modern reimagining of Cervantes’ classic story, closing around October 24.
Why October Feels So Special
There is something magical about attending OSF in October. With fewer visitors in town, it’s often easier to secure tickets and enjoy a more intimate theater experience. The autumn air lends a cozy, contemplative feel to the performances, and Ashland itself seems to glow under the vibrant fall colors. Evenings are cool enough to make you grateful for the warmth of an indoor theater—or for a hot drink shared after a show.
Your Stay at Country Willows Inn
After the curtain falls, retreat to the quiet comfort of Country Willows Inn, just a few minutes from the theaters downtown. Our five-acre estate offers wide open spaces, mountain views, and peaceful gardens that perfectly balance the energy of an evening at the theater.
Guests may choose from nine unique accommodations, some with fireplaces and soaking tubs. Each morning begins with a three-course gourmet breakfast prepared with fresh, local ingredients—an ideal way to start your day before exploring all that Southern Oregon has to offer. In the afternoons, you might unwind by the pool (weather permitting) or wander along garden paths that lead to the koi and duck pond. As evening falls, gather around the fire table to share stories of the day and take in the quiet beauty of autumn at Country Willows.
Make the Most of Your Visit
An October stay allows you to blend the best of Ashland: the cultural richness of world-class theater with the peaceful rhythms of Southern Oregon’s changing season. You might arrive to wander the gardens and settle in before an evening show, spend a day exploring town or hiking nearby trails, and then return for another performance before the festival closes. However you plan your trip, the combination of Shakespeare, fall colors, and the welcoming comfort of Country Willows makes for a getaway you won’t soon forget.
This October, let the Oregon Shakespeare Festival provide the drama and delight, while Country Willows Inn offers the rest, the beauty, and the sense of home. We would love to host you as the Shakespeare season takes its final bow.
