Things To Do
Oregon Shakespeare Festival
September is peak OSF season with a diverse lineup of classic and contemporary plays. Shows take place at several venues downtown, including the Allen Elizabethan Theatre (outdoor) and the Angus Bowmer Theatre (indoor). It’s a cultural highlight and a must-do for visitors!
Lithia Park
This beautiful 93-acre park is perfect for a leisurely stroll, picnic, or birdwatching. In September, the weather is ideal for walking the trails and enjoying fall colors beginning to appear. The park also hosts seasonal events and is a peaceful spot to unwind.
Wineries
September marks harvest time at local wineries. Popular wineries near Ashland include Weisinger Family Winery, Belle Fiore Winery, and Valley View Winery. Many vineyards offer tours and tastings, often paired with live music or food trucks.
Downtown Ashland
Browse the charming boutiques, artisan shops, and galleries along Main Street. Don’t miss local coffee shops and dessert spots for a sweet break.
Crater Lake National Park
Just about 90 minutes from Ashland, Crater Lake is stunning in early fall with crisp air and fewer crowds. Hiking, scenic drives, and boat tours are popular activities (check seasonal availability). The vibrant blue lake contrasts beautifully with autumn foliage.