Jacksonville Wine Trolley
Jacksonville Wine Trolley is on Friday, October 16, 2026 from 12:00 PM to 6:30 PM at Jacksonville-area wineries, Downtown Jacksonville in Medford, OR.
- When
- Friday, October 16, 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.
Also on Friday
- 8:00 AM 16th annual SO PrideAshlandA weekend kickoff party and three days of Pride celebration in Ashland with community events and performances.
- 8:00 AM – 5:00 PM World Famous Comedy – Marc YaffeeAshland Hills Hotel · 2525 Ashland Street, AshlandDates: 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.
- 8:00 AM 2 Family Yard/ Garage SaleMulti-family garage sale with tools, kitchenware, furniture, clothing, RV accessories, toys, electronics and antiques over several days.
- Spotlight 4:00 PM Forks & Friends Downtown Medford StrollVogel Plaza · 12 South Central AvenueKick off downtown restaurant week with chef tastings, local beverages and live music. Stroll Vogel Plaza and sample bites and drinks.
- Spotlight 4:00 PM – 8:00 PM Third Friday MedfordDowntown MedfordMonthly downtown night: shop specials, gallery openings, and artists and musicians in local businesses.
- Spotlight 4:00 PM – 8:00 PM Forks & Friends StrollDowntown Medford AssociationKickoff for Downtown Medford Restaurant Week: sample bites from local chefs with wine, beer, spirits and mocktails as you stroll downtown. Restaurant Week specials run through Oct 25.
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