Jacksonville Cottages - Nightly & Monthly Rentals in Jacksonville, Oregon

Uncorked Barrel Wine Tour in Applegate Valley Wine Country
2026-05-16 11:00 - 16:00 (America/New_York) | Applegate Valley Wine, PO Box 1215, Jacksonville, OR, 97530, United States
Come celebrate growing season with a self-guided tour of the Applegate Valley Wine Country. Fall is the perfect time to visit our 16 tasting rooms. The winegrapes have been picked, pressed, and barreled, and the winemakers have time to chat.
Pick your starting location, and let yourself be lured from one winery to the next. Each will offer an appetizer and wine for tasting. You’ll even get to meet some of the latest releases! Uncorked is a great opportunity to stock up on wine for upcoming gifts, or parties.
Tickets are $59 and include a commemorative Wine Trail wine glass.
Bonus: Designated drivers tickets are FREE and they may sample the food.

Applegate Valley Wineries Uncorked Wine Barrel Tour
2026-05-16 11:00 - 16:00 (America/Los_Angeles) | Applegate Valley, Oregon
Saturday, May 16, 11am-4pm: Applegate Valley Wineries Uncorked Wine Barrel Tour.

Special Wine Tastings & Food Pairings at 16 Applegate Wineries.

Tickets $59 each – includes a wine glass.

Tickets and more info at applegatevalley.wine

Beekman House Tours: Daily Life Then and Now
2026-05-16 12:00 - 15:00 (America/Los_Angeles) | Beekman House, 452 E California St, Jacksonville, OR, United States
An old song notes “What a difference a day makes!” Well, think about what a difference 125 years can make!
Daily Life Then and Now
1870s C.C. Beekman House, is located at 470 E. California Street in Jacksonville, Oregon.
Join Historic Jacksonville, Inc. on Saturday, May 16, 2026, for “Daily Life Then and Now” tours—a 1900 vs. 2026 comparison of a family’s daily lifestyle. Visit the difference in communication, fashion, etiquette, entertainment, chores, household “amenities,” and much more – things we take for granted like electricity, running water, and…bathrooms!

45 minute tours every half hour between noon and 3pm.
Tour admission is $8 (cash or check at the door).
All proceeds go towards maintenance of Jacksonville’s historic buildings and the programs and events that bring them to life and make them relevant for people today.

https://historicjacksonville.org/then-and-now/

Tours of Daily Life Then & Now 1900 vs 2026 at Beekman House
2026-05-16 12:00 - 15:00 (America/New_York) | Beekman House, 452 E California St, Jacksonville, OR, United States
Tours of Daily Life Then & Now 1900 vs 2026
$8 cash or check at door

Paws to Read: Read with a dog at Jacksonville Library
2026-05-16 14:00 - 15:00 (America/New_York) | Jacksonville Library, 340 W. C Street, Jacksonville, OR, 97530, United States
Paws to Read: Read with a dog

Third Saturday: Block Printing with Belinda Moffit
2026-05-16 14:00 - 17:00 (America/New_York) | Art Presence Art Center, 206 N 5th St, Jacksonville, OR, United States
Spend a creative afternoon with Belinda Moffit and learn the timeless craft of block printing. Whether you’re a total beginner or a seasoned pro, you’ll be guided through every step – from designing and carving your block to pulling your very first print. We provide all the supplies; you just bring the creativity! Registration Required,Limit 15, $40

Live Music at Rellik Winery
2026-05-16 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
2026-05-16 16:00 - 18:00 (America/New_York) | Rellik Winery, 970 Old Stage Rd, Central Point, OR, 97502
Live music by The Giantess

Live Music at Dos Mariposas Vineyards
2026-05-16 16:00 - 18:00 (America/New_York) | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States
Live music by 12 Bars Deep

Live Music at Dancin Vineyards
2026-05-16 17:00 - 19:00 (America/New_York) | DANCIN Vineyards, 4477 South Stage Road, Medford, OR, 97501, United States
Live music by Lisa & Dean

Live Music at South Stage
2026-05-16 17:30 - 19:30 (America/New_York) | South Stage Cellars, 125 S. 3rd. St, Jacksonville, OR, 97530, United States
Live music by Left
$20 Reservation

Live Music at The Wine Lounge at The Jacksonville Inn
2026-05-16 18:00 - 20:00 (America/New_York) | The Wine Lounge at the Jacksonville Inn, 175 E. California Street, Jacksonville, 97530, United States
Live music every Saturday Night! Check the website for details: The Wine Lounge Events

Live Music at The Bella Union Restaurant & Saloon
2026-05-16 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

Live Music at Bella Union Restaurant & Saloon
2026-05-16 19:00 - 22:00 (America/New_York) | Bella Union Restaurant & Saloon, 170 W. California St, Jacksonville, OR, 97530, United States
Live music by Shabby Guys

Dos Mariposas
2026-05-17 | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States

Live Music at Dos Mariposas Vineyards
2026-05-17 08:00 - 17:00 (America/New_York) | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States

Brunch at Rellik Winery
2026-05-17 10:30 - 13:00 (America/New_York) | Rellik Winery, 970 Old Stage Rd, Central Point, OR, 97502
Come join us for our weekly Sunday brunch at Rellik Winery.

Live Music at Daisy Creek Vineyards
2026-05-17 14:00 - 16:00 (America/New_York) | Daisy Creek Vineyard, 675 Shafer Lane, Jacksonville, OR, 97530, United States
Live music every Sunday afternoon! Check our website for performances: Daisy Creek Calendar

Live Music at Daisy Creek Vineyard
2026-05-17 14:00 - 16:00 (America/New_York) | Daisy Creek Vineyard, 675 Shafer Lane, Jacksonville, OR, 97530, United States
Live music by Jen Ambrose & The Mystic Trio

Live Music at Dos Mariposas Vineyards
2026-05-17 15:00 - 17:00 (America/New_York) | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States
Live music by 33 String Drive

Live Music at Rellik Winery
2026-05-17 16:00 - 18:00 (America/New_York) | Rellik Winery, 970 Old Stage Rd, Central Point, OR, 97502
Please check out our website for list of performances: Rellik’s Calendar

Live Music at Rellik Winery
2026-05-17 16:00 - 18:00 (America/New_York) | Rellik Winery, 970 Old Stage Rd, Central Point, OR, 97502
Live music by David Pinsky & Phil Newton

Live Music at Dancin Vineyards
2026-05-18 17:00 - 19:00 (America/New_York) | DANCIN Vineyards, 4477 South Stage Road, Medford, OR, 97501, United States
Live music by Shae & Jenni

City Council Work Session
2026-05-19 12:00 - 14:00 (America/Los_Angeles) | Jacksonville City Hall, 206 N 5th St, Jacksonville, OR, United States
All meeting held at New City Hall Assembly Room (NCHAR) – Citizens Welcome! CITY COUNCIL MEETING: Tuesday, May 5, 6pmPLANNING COMMISSION MEETING: Wednesday, May 13, 6pmCITY COUNCIL WORK SESSION: Tuesday, May 19, noonBUDGET COMMITTEE MEETING: Thursday, May 21, 4pmHISTORIC & ARCHITECTURAL REVIEW COMMISSION (HARC): Wednesday, May 27, 5pm

CITIZENS FOR A SAFER JACKSONVILLE: TOWN HALL MEETING
2026-05-19 17:30 - 18:30 (America/Los_Angeles) | Jacksonville Library, 340 W. C Street, Jacksonville, OR, 97530, United States
Jacksonville Review – May 2026

THERE WILL BE A TOWN HALL on Tuesday, May 19, from 5:30-6:30pm, in the Naversen Meeting Room at the Public Library, at 340 W. C Street.
Organizers expect a good turnout with our new Police Chief, Matt Hannum, who will be on hand to answer any questions about the new changes to the JPD, including some you may have already seen! As many know, there is a new, weekly post on the JPD Facebook page, which includes many of the calls the department has recently responded to. Thanks to increased presence, the number of speeding incidents is being reported. Additionally, we expect City Councilors, Andrea Thompson and Talon Reed, will be attending.
The main purpose of the meeting is to provide residents with an opportunity to get their questions and concerns heard and addressed. We are kindly asking the public to listen to one another and be respectful during the Q & A session. Public discourse is critical to resolving misinformation and solving issues. We expect a lively and healthy discussion!
Also, printed signs which say NO NEED FOR SPEED, will be available for sale for $7. Signs are intended to be placed on private property as a gentle reminder to all citizens to respect residents/seniors, pets, and the abundance of wildlife we all enjoy.
The Citizens for a Safer Jacksonville looks forward to hosting this event. For more information, please contact Cindy Rasmussen at Jvillesafety@gmail.com.

Jacksonville Review – April 2026
GREETINGS TO ALL OUR NEIGHBORS! We are looking forward to welcoming Spring to our town, and it seems an appropriate time to provide everyone with an update of our 2026 goals and objectives, plans, and new ideas! With our new Police Chief, Matt Hannum, and a full staff of Police Officers, we are anticipating many new, creative ideas for increased collaboration and transparency in the coming months and years. Safety, AS ALWAYS, is in the forefront for the Police Department and our entire citizenry. Our mission is to work with our town leadership and the police to enhance pedestrian, biker and pet safety, as we build a place where we all care for and help our neighbors.
I hope you saw the column in the March Review from 15-year-old contributor Cora Campanella, who was in a very scary automobile accident recently, and who wrote about it in her article, ‘’SAFE DRIVING … PLEASE!” To quote her, “In a small town like Jacksonville, the roads don’t just belong to cars. They also belong to residents, families, and tourists exploring our historical town. The speed limit through Jacksonville has been a source of debate. However, slowing down gives you the extra seconds you may need to notice a child riding their bike, or another driver being reckless.”
I couldn’t have said it any better. This is why our work is so important.
Thank You, Cora, for reminding us of what is at stake when we are in a hurry, and we may not be paying attention.
Please Mark Your Calendars for a TOWN HALL MEETING on Tuesday, May 19, at the Jacksonville Library Naversen Room, from 5:30-6:30pm, to hear from YOU about concerns, suggestions, and about our plans to keep improving safety in town. Please join us for a productive discussion.
For more about Citizens for a Safer Jacksonville, contact Cindy Rasmussen at Jvillesafety@gmail.com, or 510-406-3954.

Tuesday Tunes at The Wine Lounge at The Jacksonville Inn
2026-05-19 18:00 - 20:00 (America/New_York) | The Wine Lounge at the Jacksonville Inn, 175 E. California Street, Jacksonville, 97530, United States
Catch live music at The Wine Lounge at Jacksonville Inn every Tuesday night.

Catch live music at The Wine Lounge at Jacksonville Inn every Tuesday night. The Lounge offers a wide selection of local wines to try by the glass or bottle (No Corkage fee!), and a nice complimentary menu to nosh on. This is a great local hang.

Live Music at Jacksonville Community Center
2026-05-20 08:00 - 17:00 (America/New_York) | Jacksonville Community Center, 160 E. Main St, Jacksonville, OR, 97530, United States

Preschool Music & Movement – Weekly on Wednesdays 11am-Noon
2026-05-20 11:00 - 12:00 (Asia/Dubai) | Jacksonville Community Center, 160 E. Main St, Jacksonville, OR, 97530, United States
At Jacksonville Community Center every Wednesday 11am – Noon, discover the joy of music in this engaging class designed for children 2-5 and their caregivers. This class combines singing, rhythm, movement and sign language. Get ready to sing beloved songs from around the world, and make music together in this weekly class! Sponsored by Jackson Care Connect. ADULTS ARE FREE attending with child(ren). $5 per child. Walk-ins ALWAYS welcome.
Instructor Bios: Laurie Finear has been a music teacher in the Rogue Valley for over 15 years as a certified Music Together teacher. She now creates and teaches her own music classes for children and their caregivers in Ashland and Jacksonville. She is passionate about sharing the joy of music with children and families.

Experimentation Station: Volcanoes at Jacksonville Community Center
2026-05-20 14:00 - 15:00 (America/New_York) | Jacksonville Community Center, 160 E. Main St, Jacksonville, OR, 97530, United States
Experimentation Station: Volcanoes
Age 6+
$5 event cost

Pinot & Pages at Hummingbird Estate
2026-05-20 17:00 - 19:00 (America/New_York) | Hummingbird Estate, OR, 97502, United States
Attention all writers! Join us every Wednesday from 5-7pm. Grab a glass of wine & let the words flow!
Bring your journal or laptop and join a table of fellow writers for focused, quiet writing time. It’s not a workshop or a class-just a chill space to show up, sip and let the words flow. RSVP not required.
