Discovering Southern Oregon – October 2025

ONE OF THE THINGS I LOVE MOST about Southern Oregon is its four distinct seasons. While I can’t say I have a single favorite, I do have go-to activities for each. Fall is all about crisp air, colorful leaves, pumpkin harvests, cider brewing, and the comfort of a warm fire. It’s the season for scenic drives, live music, and cozy moments. Here are my top 10 favorite ways to celebrate fall in Southern Oregon:

  1. Scenic Fall Drives—The changing colors of maples, alders, dogwoods, aspens, and oaks are spectacular. Some of the best places to enjoy the foliage are Jacksonville, Ashland, the Applegate Valley, and the Rogue-Umpqua Scenic Byway. Stroll through Jacksonville’s historic downtown, wander Ashland’s Lithia Park, enjoy views from Lindsay Lodge, or take in the brilliance along the Rogue and Umpqua rivers.
  2. Live Music Moves Inside—Few things feel more “fall” than live music in a warm fire or intimate setting. Favorite spots include South Stage Cellars, Bella Union, Daisy Creek, DANCIN, Rellik, and newer venues like Remotion, and the Wine Lounge at the Jacksonville Inn.
  3. Wine Tasting in the Countryside—Fall colors pair perfectly with wine. There’s no better way to enjoy the fall colors than by visiting local wineries. Take a ride on Jacksonville’s Wine Trolley, which lets you hop on and off at different wineries without worrying about driving. You can also take a self-guided tour of the Applegate Valley’s 18 tasting rooms, where winemakers will be ready to chat after the harvest. Private wine tours are also available with companies like Wine Hopper.
  4. Hiking to Colorful Waterfalls—South of Prospect, Mill Creek Falls and Barr Creek Falls shine in autumn. The 1.4-mile loop from the Mill Creek Falls Trailhead takes you through the “Avenue of the Boulders” before revealing two incredible waterfalls framed by fall foliage.
  5. Holiday Lights—As evenings grow longer, the region lights up. Jacksonville kicks off its Victorian Christmas with a tree lighting ceremony at the end of November just in time for the Holiday Trolley Lights Tour in December. Ashland also dazzles with festive downtown displays.
  6. Halloween Celebrations—Jacksonville’s Halloween Promenade fills downtown with candy, costumes, and family fun. Ashland’s Halloween Parade brings both kids and adults downtown in creative costumes for a lively Main Street celebration.
  7. Pheasant Fields Farm Harvest Festival—This 20-acre farm in Medford celebrates its 20th annual Harvest Festival with a pumpkin patch, corn maze, hayrides, animal exhibits, and more—all set against the colorful backdrop of Southern Oregon hills.
  8. Oysters & Ales at Bella Union—Every Thursday night from October through April, Bella Union hosts its popular Oysters & Ales event. Enjoy BBQ oysters and beer samples from a featured brewery, or indulge in their delicious Italian food, live music, and cozy atmosphere.
  9. Watching Football with Friends—Whether you’re a fan of the Ducks, Beavers, Seahawks, 49ers, or another team, fall weekends are perfect for gathering with friends to watch football. Whether at home or in one of Jacksonville’s local saloons, it’s a great way to spend a fall afternoon.
  10. Romantic River Getaways—Fall is an ideal time for a riverside staycation. With fewer rafters on the water and stunning fall colors, my three favorite spots are Morrison Lodge on the Rogue River in Galice, Tu Tu’ Tun Lodge near Gold Beach, and Steamboat Inn on the Umpqua River.

As the leaves begin to fall and the trees turn brilliant shades of red and yellow, don’t think of it as the end of summer, see it as the start of fall and all the wonderful activities the season brings.