Jacksonville Cottages - Nightly & Monthly Rentals in Jacksonville, Oregon

Trivia Night at Dos Mariposas Vineyards
2026-05-27 18:00 - 20:00 (America/New_York) | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States
Trivia Night

Jacksonville Woodcarvers - Beginners Welcome!
2026-05-28 09:00 - 11:00 (America/Los_Angeles) | 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.

Art Presence Art Center: Spring After School Art Club
2026-05-28 15:00 - 16:00, 2026-05-29 15:00 - 16:00 (America/Los_Angeles) | Art Presence Art Center, 206 N 5th St, Jacksonville, OR, United States
Event Title: Art Presence Art Center: Spring After School Art Club
Event Date: April 2nd- May 29th
Event Start Time: 3:00PM
Event End Time: 4:00PM
Description of Event:
Come make art with us after school! If you are a 1st-5th grader and you love making art, come join us at Art Presence every Thursday or Friday from 3:00-4:00.
We currently accepting registrations for Spring 2026.
Register now, as enrollment is limited to 15 students per unit. We are pleased to offer a low enrollment fee of $10 per unit and you can register online. See you after school!
*Winter After School Art Club is possible thanks to the generous support for our local community through our ‘Y’art Sale’ fundraising event.
*Spring After School Art Club is possible thanks to generous funding from the Carpenter foundation and is supported in part by a grant from the Jackson County Cultural Coalition funded by the Oregon Cultural Trust, investing in Oregon’s arts, humanities and heritage

Happy Hour at Dos Mariposas Vineyards
2026-05-28 15:00 - 19:00 (America/New_York) | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States
Happy Hour Specials

$3 tacos
$2 off a glass of wine or beer with any food purchase
Free chips & salsa with bottle purchase

Complimentary Wine Tasting at Jacksonville Inn Wine Lounge
2026-05-28 16:00 - 18:00 (America/New_York) | The Wine Lounge at the Jacksonville Inn, 175 E. California Street, Jacksonville, 97530, United States
Complimentary Wine Tasting

Art Club Workshop at The Miners’ Bazaar
2026-05-28 17:00 - 20:00 (America/New_York) | The Miners’ Bazaar, 235 E. California Street, Jacksonville, OR, 97530, United States
Join us every Thursday to dive into creative adventures with other makers! No medium restrictions or sketchbooks necessary. This “Club” is created to bring us Makers and Creatives into a space to connect and make together. Bring your own mediums of choice, a sketchbook or any surface or project to play with. There will be weekly prompts, various mediums available to dive into and play with (Project Fees may apply), demos and monthly Giggle Water Specials! Cost: Free!

Art Club at The Miners’ Bazaar
2026-05-28 17:00 - 20:00 (America/New_York) | The Miners’ Bazaar, 235 E. California Street, Jacksonville, OR, 97530, United States
Join us every Thursday to dive into creative adventures with other makers! No medium restrictions or sketchbooks necessary. This “Club” is created to bring us Makers and Creatives into a space to connect and make together. Bring your own mediums of choice, a sketchbook or any surface or project to play with. There will be weekly prompts, various mediums available to dive into and play with (Project Fees may apply), demos and monthly Giggle Water Specials! Cost: Free!
Unless otherwise noted, all workshops can be reserved here: https://www.theminersbazaar.com/store

Dancing Cats 3 Course Dinner – Tri Tips at Hummingbird Estate
2026-05-28 18:00 - 19:00 (America/New_York) | Hummingbird Estate, OR, 97502, United States
Dancing Cats 3 Course Dinner – Tri Tips
$28 Reservation

Live Music at Bella Union Restaurant & Saloon
2026-05-28 19:00 - 21:00 (America/New_York) | Bella Union Restaurant & Saloon, 170 W. California St, Jacksonville, OR, 97530, United States
Join us for live music, food and spirits every Thursday night!
Check our website for list of entertainment: Live Music at the Bella

Live Music at Bella Union Restaurant & Saloon
2026-05-28 19:00 - 21:00 (America/New_York) | Bella Union Restaurant & Saloon, 170 W. California St, Jacksonville, OR, 97530, United States
Join us for live music, food and spirits every Thursday night!
Live music by Chris Baron
Check our website for list of entertainment: Live Music at the Bella

Complimentary Wine Tastings at The Wine Lounge at The Jacksonville Inn
2026-05-29 16:00 - 18:00 (America/New_York) | The Wine Lounge at the Jacksonville Inn, 175 E. California Street, Jacksonville, 97530, United States
The Wine Lounge at Jacksonville Inn offers complimentary tastings every Friday from 4-6PM.
Come hungry, they have a great little menu as well.

Live Music at Daisy Creek Vineyards
2026-05-29 16:30 - 18:30 (America/New_York) | Daisy Creek Vineyard, 675 Shafer Lane, Jacksonville, OR, 97530, United States
Live music every Friday! Check our calendar for performances: Daisy Creek Calendar

Live Music at Dancin Vineyards
2026-05-29 17:00 - 19:00 (America/New_York) | DANCIN Vineyards, 4477 South Stage Road, Medford, OR, 97501, United States
Live music by David Pinsky & Phil Newton

Friday Nights Live Music at Hummingbird Estate
2026-05-29 18:30 - 20:30 (Asia/Dubai) | Hummingbird Estate, OR, 97502, United States
Join us for an evening of music from 6:30-8:30pm on our side lawn, now featuring a brand new stage platform! Enjoy delicious eats from Pizza Mia and relax in the Hummingbird atmosphere. Bring a lawn chair for comfortable seating. Food truck starts at 6:00pm. Come early, grab a bite, and settle in for a great night.

Live Music at The Bella Union Restaurant & Saloon
2026-05-29 19:00 - 22:00 (America/New_York) | Bella Union Restaurant & Saloon, 170 W. California St, Jacksonville, OR, 97530, United States
Join us for live music, great food and spirits every Friday & Saturday
Check our website for list of entertainment: Live Music at the Bella

Jacksonville “Walk Through History” Tour
2026-05-30 10:00 - 11:00 (America/Los_Angeles) | Jacksonville City Hall, 206 N 5th St, Jacksonville, OR, United States
Walk through Jacksonville History!
JACKSONVILLE, OR—Jacksonville’s “Walk through History” tours are back! At 10 a.m. every Saturday from May 30th through September 5th, Historic Jacksonville, Inc. will be offering one-hour guided walks through Jacksonville’s National Historic Landmark District, the first on the West Coast! Participants will take a stroll through history, visiting government and commercial buildings, fraternal lodges, and homes that capture the stories of the people who transformed a gold rush town into Southern Oregon’s 19th Century social, governmental, and commercial hub. They’ll learn how gambling money built a church; how the Civil War ended a successful mercantile partnership; how a saloon housed the county’s first museum; how fire reshaped the town; and how a railroad both destroyed the town and preserved it.
Walking tours leave from Jacksonville’s New City Hall (the historic “Courthouse Square”) at 206 North 5th Street between West C and D streets and cover about one mile with multiple stops. Tours are FREE but donations are encouraged! All monies go towards the preservation and maintenance of Jacksonville’s historic buildings.
For individuals who prefer not to “stretch their legs,” Historic Jacksonville’s website (https://www.historicjacksonville.org) offers numerous ways to explore Jacksonville virtually. These include multiple blogs about the town and its settlers along with three video tours that introduce viewers to Jacksonville’s Historic Landmark District, its Historic Homes, and its Pioneer Cemetery.
Historic Jacksonville, Inc. invites you to forget the “names, dates, places, and battles” version of history you may have been taught in school. HJI’s live and virtual tours are about “real history”—people and their stories. They are about life!
Additional information on “Walk through History” and other Historic Jacksonville, Inc. tours is available at 541-245-3650; info@historicjacksonville.org; and www.historicjacksonville.org.

Guided History Walking Tour – about 1 mile
2026-05-30 10:00 - 11:00 (America/New_York) | Jacksonville City Hall, 206 N 5th St, Jacksonville, OR, United States
Donation

Beekman Bank Behind the Counter Tours
2026-05-30 11:00 - 15:00 (America/Los_Angeles) | Beekman Bank 1863, 400 W California St, Jacksonville, OR, United States
Step behind the counter of the historic Beekman Bank. Every weekend May 23 – September 6, 2026, 11am-3pm Oldest bank in the Pacific Northwest!Over $40 million in gold crossed its counters in the 1800s.(Equal to $1.5 billion+ today!) FREE – Donations welcomed! 110 W. California Street, Jacksonville, Oregon 97530 https://www.historicjacksonville.org/behind-the-counter-tours/

Experience how banking was conducted in the late 1800’s
2026-05-30 11:00 - 15:00 (America/New_York) | Beekman Bank, corner of California and North 3rd streets, Jacksonville, OR, 97530, United States

Live Music at Daisy Creek Vineyards
2026-05-30 13:00 - 15:00 (America/New_York) | Daisy Creek Vineyard, 675 Shafer Lane, Jacksonville, OR, 97530, United States
Music Bingo

Paws to Read: Read with a dog
2026-05-30 14:00 - 15:00 (America/New_York) | Jacksonville Library, 340 W. C Street, Jacksonville, OR, 97530, United States

Artist & Gardener 10th-Anniversary Celebration!
2026-05-30 14:00 - 17:00 (America/Los_Angeles) | Artist and Gardener, 130 S 3rd St, Jacksonville, OR, United States
Come help us celebrate 10 years of Artist & Gardener at our little corner of town on May 30, 2026. We have much to be thankful for and want to share the joy we feel with those that helped make it possible. Food and drink will be provided in the garden. 2pm–?130 South Third Street, Jacksonville 541-702-2555

Live Music at Rellik Winery
2026-05-30 16:00 - 18:00 (America/New_York) | Rellik Winery, 970 Old Stage Rd, Central Point, OR, 97502
Please check out our calendar for list of performances: Rellik Winery Calendar

Live Music at Rellik Winery
2026-05-30 16:00 - 18:00 (America/New_York) | Rellik Winery, 970 Old Stage Rd, Central Point, OR, 97502
Live music by Sterling Vintage Jazz
Please check out our calendar for list of performances: Rellik Winery Calendar

Live Music at Dos Mariposas Vineyards
2026-05-30 16:00 - 18:00 (America/New_York) | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States
Live music by Hopstone
