Jacksonville Cottages - Nightly & Monthly Rentals in Jacksonville, Oregon

Second Saturdays: Jacksonville Jubilee
2026-09-12 14:00 - 18:00 (America/Los_Angeles) | Downtown, Jacksonville, OR, United States
Welcome to the Jacksonville Jubilee! Join us for the first of a new monthly tradition celebrating the history, culture, creativity, and community spirit that make Jacksonville so special.Held on the second Saturday of each month, Jacksonville Jubilee is inspired by our town’s rich heritage and the timeless charm that has drawn visitors here for generations. This year is especially meaningful as we celebrate the 60th anniversary of Jacksonville’s designation as a National Historic Landmark community. Our June Jubilee is a soft launch—a chance to gather, explore, and help us begin shaping what will become an evolving monthly celebration. As the event grows, you’ll find new activities, special themes, historic experiences, live entertainment, shopping, dining, and opportunities to connect with the people and stories that make Jacksonville unique.This month, enjoy:• Live music throughout town• Local art exhibits and gallery experiences• Shops staying open later for evening browsing• Special offerings from participating businessesStroll Jacksonville’s historic streets, discover local businesses, enjoy a meal or glass of wine, and experience the welcoming atmosphere of one of Oregon’s most beloved small towns.Whether you’re a longtime local or visiting for the first time, we invite you to be part of the beginning. Join us this Saturday—and come back each month as Jacksonville Jubilee continues to grow into a celebration worthy of Jacksonville’s remarkable history.We can’t wait to see you downtown.

Troon Vineyard & Farm Sunday Summer Market
2026-09-13 12:00 - 16:00, 2026-09-20 12:00 - 16:00, 2026-09-27 12:00 - 16:00 | Troon Vineyard & Farm, 1475 Kubli Rd, Grants Pass, OR, United States
As the days get longer and the sun is out in full force, we find ourselves looking forward to summer solstice and the start of our 2nd annual Sunday Summer Market.

Featuring local farmers, artisans, and garden-to-guest lunches by Chef Carl Krause, Sunday Summer Markets at Troon will offer our community members and winery visitors a point of access to sustainably-sourced food and hand-crafted items.

Bring your friends and family, and come on out to sip a glass of wine in the garden while perusing local goods and enjoying live music. Our opening market will be on Sunday, June 21st from 12:00 to 4:00 pm.

https://www.troonvineyard.com/

*Calling All Vendors: If you are a local farmer or artisan, and are interested in participating, we still have a limited number of vendor spots open. Email natalie@troonvineyard.com for a vendor application.

Jacksonville Woodcarvers - Beginners Welcome!
2026-09-17 09:00 - 11:00, 2026-09-24 09:00 - 11:00, 2026-10-01 09:00 - 11:00, 2026-10-08 09:00 - 11:00, 2026-10-15 09:00 - 11:00, 2026-10-22 09:00 - 11:00, 2026-10-29 09:00 - 11:00, 2026-11-05 09:00 - 11:00 and 12 more dates | Jacksonville Library, 340 W. C Street, Jacksonville, OR, 97530, United States
Thursdays 9-11am: JacksonvilleWoodcarvers. Jacksonville Library,Naversen Room (use librarian parking lot entrance).

All are welcome – we encourage and have support for beginning carvers – please join us!
The library is closed when we meet – please use side door to Naversen Room in the librarian parking lot.

Jacksonville ART RUSH Weekend
2026-10-09 - 2026-10-11, 2026-11-13 - 2026-11-15, 2026-12-11 - 2026-12-13, 2027-01-08 - 2027-01-10 | downtown jacksonville, oregon
Jacksonville Chamber of Commerce Events:

2nd Friday Art Rush, at participating businesses in town.

https://jacksonvilleoregon.org/events/

Food Project Jacksonville Pickup Day
2026-10-10, 2026-12-12 | OR
Medford Food Project – Jacksonville Pickup Day
(Always the 2nd Saturday of even-numbered months.)
Please contact Jerrine Rowley at 541-702-2223 or Faye Haynes at 541-324-1298 if you have any questions or wish to become involved with the Food Project in Jacksonville!
