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Jacksonville Wine Trolley

Jacksonville Wine Trolley is on Saturday, October 17, 2026 from 12:00 PM to 6:30 PM at Jacksonville-area wineries, Downtown Jacksonville in Medford, OR.

When

Saturday, October 17, 2026, 12:00 PM – 6:30 PM

Where

Jacksonville-area wineries, Downtown Jacksonville

Cost

See event details

Hop-on, hop-off trolley between Jacksonville-area tasting rooms. $30 day pass, $45 three-day, $15 happy-hour pass after 3 PM.

Event details

Also on Saturday

• 7:00 AM World Famous Comedy – Marc YaffeeAshland Hills Hotel · 2525 Ashland Street, Ashland

  Dates: Friday, October 16 & Saturday, October 17, 2026 Doors: 6:30 PM Show: 7:30 PM Venue: The Stardust Lounge at Ashland Hills Hotel & Suites Address: 2525 Ashland St., Ashland, OR Tickets: $25 Age: 21+ Food & Drinks: Luna Cafe Additional: Limited VIP Meet & Greet and weekend hotel packages available.
• Spotlight 8:00 AM 16th annual SO PrideAshland

  Three days of Pride celebrations in Ashland with parades, parties, performances, and community events marking the 16th anniversary. Activities for all ages throughout the weekend.
• 8:00 AM Hometown Harvest at Grange Co-op Medford2531 S Pacific Hwy

  Celebrate local fall produce, vendors and community activities at the co‑op. Expect seasonal foods, samples and family-friendly happenings.
• 8:30 AM – 1:00 PM Ashland Saturday MarketOak Street, downtown Ashland · 100 block of Oak St, Ashland

  Rogue Valley Growers & Crafters Saturday market between Main St and Lithia Way.
• Spotlight 12:00 PM – 5:00 PM Bales & Ales at Common BlockCommon Block Brewing Co. · 315 E 5th St

  Pumpkin carving and live music on the patio, with a free pumpkin with purchase.
• Spotlight 3:00 PM – 5:00 PM The Tommy Dorsey Orchestra with Hayden Grove: Tribute to Frank SinatraCraterian Theater at The Collier Center · 23 S Central Ave, Medford

  Enjoy a swinging big‑band tribute to Frank Sinatra performed by the Tommy Dorsey Orchestra with guest vocalist Hayden Grove.

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