Historic streets, nearby hills and a calendar shaped by art and community gatherings.
CALIFORNIA STREET · JACKSONVILLEPhoto: Joe Mabel · CC BY-SA 4.0 · Resized and cropped to fit; reuse terms retained
Check the official forecast for current conditions.
Open an event here for its summary, admission and source. This is a partial selection; organizers can change or cancel a date.
Activity filters match the listing’s wording; confirm ages and participation with the organizer. Free entry includes only listings with an explicit admission note. Food, purchases and optional activities may cost extra.
5 matching listings · Upcoming
When: Thu, Nov 12 · 04:00 PM - 05:00 PM (Pacific time)
Where: Jacksonville Community Center
Confirm details with JPR community calendar ↗When: Fri, Nov 13 · 04:30 PM - 06:00 PM (Pacific time)
Where: Jacksonville Community Center
Confirm details with JPR community calendar ↗When: Wed, Nov 18 · 02:00 PM - 03:00 PM (Pacific time)
Where: Jacksonville Community Center
Confirm details with JPR community calendar ↗When: Mon, Nov 23–Tue, Nov 24 · 12:00 p.m.–2:00 p.m. (Pacific time)
Where: Ruch Outdoor Community School · 156 Upper Applegate Road · Jacksonville
Confirm details with Applegate Valley Connect calendar ↗When: Fri, Dec 11 · 6:30 p.m.–8:30 p.m. (Pacific time)
Where: Jacksonville Community Center · 160 E. Main St · Jacksonville
Confirm details with Applegate Valley Connect calendar ↗These venues are in Medford. Check the actual address and travel before choosing.
Activity filters match the listing’s wording; confirm ages and participation with the organizer. Free entry includes only listings with an explicit admission note. Food, purchases and optional activities may cost extra.
5 matching listings · Upcoming
When: Tue, Nov 17 · Time not confirmed (Pacific time)
Where: Medford Police Department, 219 S. Ivy Street, Medford 97501
Confirm details with City of Medford ↗When: Tue, Nov 24 · 06:00 PM - 07:30 PM (Pacific time)
Where: Medford Library
Confirm details with JPR community calendar ↗An illuminated parade, performances, tree lighting, food trucks and holiday festivities downtown.
When: Sat, Dec 5 · 5–8 p.m. (Pacific time)
Admission: Free
Where: Pear Blossom Park, 204 N. Bartlett Street, Medford
Read full event details →Breakfast, activities and a visit with Santa. Everyone must register; check the city page when registration opens.
When: Sat, Dec 12 · 8:30–11 a.m. (Pacific time)
Admission: Registration required; ages 12 and under free, adults $7 resident or $9 nonresident
Where: Rogue X, 901 Rossanley Drive, Medford
Read full event details →When: Fri, Mar 19 · Time not confirmed (Pacific time)
Where: RogueX, 901 Rossanely Drive, Medford 97501
Confirm details with City of Medford ↗Fetch times describe the calendar connection, not a new editorial verification of every event. Sources delayed or unavailable may leave gaps.
More date and activity filters for Jacksonville → · All Rogue Valley events →
These are evergreen places and activities, separate from scheduled events. Published visitor details are a dated snapshot; follow the source for today's opening and access.
Historic Jacksonville tasting room with food, an outdoor patio and music.
A downtown choice for combining wine with a walking visit. Use the current menu and events pages to match your date.
Visit details on RVN → · Official information / booking ↗A Jacksonville winery option for a town-focused tasting day.
Consult the winery directly for current tasting hours and upcoming-event details.
Visit details on RVN → · Official information / booking ↗Wine and food on Old Stage Road near Jacksonville.
970 Old Stage Road has a Central Point postal address. Published Monday–Thursday 11:30–7, Friday/Saturday 11:30–8, Sunday 10:30–7.
Visit details on RVN → · Official information / booking ↗Wine tasting in Jacksonville’s historic Orth House, with accommodation upstairs.
105 West Main Street. Choose a tasting visit or a separate lodging booking.
Visit details on RVN → · Official information / booking ↗Sunday market; confirm the current-year session in the city calendar.
The organizer’s homepage still displays 2025 season dates. Use the city’s current calendar rather than applying those dates to 2026.
Visit details on RVN → · Official information / booking ↗A historic woodland path starting near Britt Gardens and the town center.
Access and planning: The length is the trail segment, not a round trip. Use the Woodlands map to make a loop.
Route details on RVN → · Official map and notices ↗A quieter woodland entry from the Beekman House parking area.
Access and planning: Check the signed junctions and the Woodlands map; horses are not permitted in this system.
Route details on RVN → · Official map and notices ↗Walk from Jacksonville's historic core into a connected wooded hillside network.
Access and planning: There are multiple trailheads and intersecting routes. Bring the current map.
Route details on RVN → · Official map and notices ↗Food and estate wine in a vineyard setting.
4477 South Stage Road. Check the food menu and book the dining experience you want.
Visit details on RVN → · Official information / booking ↗Pinot Noir and Chardonnay with a food menu and vineyard setting.
4477 South Stage Road, Medford. Use the current menu and reservation link to plan a meal with your tasting.
Visit details on RVN → · Official information / booking ↗Hillcrest estate tasting with a substantial public music and activity calendar.
3283 Hillcrest Road, Medford. The tasting room publishes Sunday–Wednesday noon–7 p.m. and Thursday–Saturday noon–9 p.m. Choose a tasting flight, glass or bottle; indoor and heated outdoor seating are available. Check individual event hours and reservation terms separately; a tasting visit is different from a ticketed event.
Visit details on RVN → · Official information / booking ↗A working Medford farm offering wine alongside farm food and music.
2881 Hillcrest Road, Medford. Consult the farm’s own calendar and food service information for the visit you want.
Visit details on RVN → · Official information / booking ↗Wine, cider and food at a Medford vineyard with a pond and lavender.
3976 Bellinger Lane. Through October 31, 2026: Thursday 3–7, Friday/Saturday noon–8, Sunday noon–7. A different winter schedule starts November 1.
Visit details on RVN → · Official information / booking ↗Activity directory sources reviewed October 4, 2026; trail sources reviewed September 27, 2026. Individual listings may show a later source review. This selection does not cover every option.
Compare all activity guides →Choose a starting point, then check conditions before you go.
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