RoxyAnn Winery

Pups & Pours: Doggie Dash Demo
2026-06-19 10:00 - 14:00 (America/Los_Angeles) | Oregon
Doggie Dash is Southern Oregon’s mobile dog-running service, offering safe and structured runs on non-motorized treadmills.
They will be at the winery on from 10 am to 2 pm, and when you purchase an intro run for just $10, you will receive 10% off a cup of coffee at Roxy Coffee or a glass of wine at RoxyAnn Winery.

MUSIC + WINE SERIES FEATURING Mercy
2026-06-19 18:00 - 20:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Join us at RoxyAnn Winery for a Friday night of dancing and fun as we welcome Southern Oregon’s Mercy to the tasting room! Based in beautiful Southern Oregon, Mercy Featuring Lynda Day is one of the premier acts in the region. Attending a Mercy performance is more than just attending a concert or dancing at your favorite club or winery. Rather, it’s an experience…

Listen to live dance-worthy music while sipping on some delicious & award-winning wines, or crisp & refreshing beer from the tap: grab all your friends and make a night of it!

This event is free, but we are taking reservations so please call the Tasting Room to reserve your spot! (541) 776-2315, Option 1

We encourage you to come a little early to settle in to your seats, order food, grab your drinks, and get ready to dance the night away!

Rick Millward Presents Open Mic
2026-06-20 15:00 - 17:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
The RoxyAnn Open Mic will be this Saturday, and we’ve come up with a way to make 2026 bigger and more exciting. In October the top 3 from the previous 8 month’s shows will win a paid date on a Friday Night at RoxyAnn!
Here’s how it works:
We’ll have a regular show every month through August, and then the 8 monthly winners* will be featured in the semi-final September show, each playing 3 songs. The top three vote getters will then go on to play a Friday in October, sharing a two hour finale and getting paid $100 for a 30 min set!
In addition we’ve added a $15 RoxyAnn Gift Card for for the second most votes every month.
Sound Good? Email Rick Millward at rocknm@charter.net to reserve your spot in the show and start your quest for a paid gig! Be sure to tell your friends, fans and family to come out and support your performances!
* For this contest you can only win once this year, but you’ll have 8 chances
A tie will be decided with a coin toss
One vote per performer or audience member
Singer/Songwriter Rick Millward lived and worked on the West Coast until moving to Nashville in 2000. He was part of the Music City songwriter community, collaborating with other artists and producing over 30 projects in his boutique studio, including two EMMY nominated soundtracks. Now in Southern Oregon, Rick has discovered a vibrant local music scene centered around the many tasting rooms.
This event is free and we do not take reservations for attending this specific event, so we recommend arriving early to claim your spot! Call the Tasting Room at (541) 776-2315, Option 1 with any questions.

MUSIC + WINE SERIES FEATURING Jared Gutridge
2026-06-21 16:00 - 18:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Rogue Valley based duo of acoustic singer/songwriters.
Join us at RoxyAnn Winery for a Sunday afternoon of dancing and fun as we welcome Southern Oregon’s Jared Gutridge to the tasting room! Listen to live music while sipping on some delicious & award-winning wines, or crisp & refreshing beer from the tap: grab all your friends and make a night of it!
This event is FREE but we are taking reservations, so please call the Tasting Room to reserve your spots! (541) 776-2315, Option 1

We encourage you to come a little early to settle in to your seats, order food, grab your drinks, and get ready to dance the night away!

Member Monday (still open to the public!)
2026-06-22 16:00 - 19:00, 2026-06-29 16:00 - 19:00, 2026-07-06 16:00 - 19:00, 2026-07-13 16:00 - 19:00, 2026-07-20 16:00 - 19:00, 2026-07-27 16:00 - 19:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Calling all RoxyAnn Winery Wine Club Members! Now, you can enjoy Member Monday every Monday! Every week from 4pm to 7pm, come enjoy time with other RoxyAnn Winery Wine Club Members, and special $5 pricing on that month’s Member Monday picks!
Are you not enjoying the perks of the RoxyAnn Winery Wine Club yet?! Sign up to become a member today and enjoy…
4 FREE tastings per month, and a FREE tasting for up to 2 guests!
Discounts on glasses, bottles, and cases of wine!
10% off tap beers in the Tasting Room!
10% off weekly live music events!
Exclusive venue rental pricing!
Invitations to private RoxyAnn Winery events + parties!
SO MUCH MORE!
To learn more or to sign up for our Wine Club and start enjoying Member Perks TODAY click HERE

Music Bingo
2026-06-24 18:00 - 20:00, 2026-07-01 18:00 - 20:00, 2026-07-08 18:00 - 20:00, 2026-07-22 18:00 - 20:00, 2026-07-29 18:00 - 20:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Join us at RoxyAnn Winery for a fun and family-friendly game of Musical Bingo! Play along while sipping on some delicious & award-winning wines, a crisp & refreshing beer from the tap, or a mocktail. Grab all your friends and make a night of it! Music theme will be announced prior to the event and dressing up is encouraged! Best dressed will win a $20 gift card.
This event is FREE entry, but this event fills up fast so reserve your spot now! (541) 776-2315, Option 1. Bring cash to purchase bingo cards and arrive early; they sell out fast! Then settle in to your seats, order food and grab your drinks.

MUSIC + WINE SERIES FEATURING Blue Lightning - Wait List Only
2026-06-26 18:00 - 20:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Established over 30 years ago in Ashland Oregon, Blue Lightning has evolved into a high energy dance band with tight grooves and lush vocal harmonies.

Join us for a Friday night full of good times, dancing and fun! Listen to amazing music while sipping on some delicious & award-winning wines, or crisp & refreshing beer from the tap! Make a night of it and grab some dinner from our on-site food trucks or our light plated menu in the tasting room.

Reservations are FULL at this point in time, please call the Tasting Room to get on the wait list at (541) 776-2315, Option 1

We encourage you to come a little early to settle in, order food, grab your drinks, and get ready to dance the night away!

MUSIC + WINE SERIES FEATURING Vanessa Finney Jazz Duet
2026-06-28 16:00 - 18:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Vanessa is a singer based in Ashland, OR.
Join us at RoxyAnn Winery for a Sunday afternoon of dancing and fun as we welcome Southern Oregon’s Vanessa Finney to the tasting room! Listen to live music while sipping on some delicious & award-winning wines, or crisp & refreshing beer from the tap: grab all your friends and make a night of it!
This event is FREE but we are taking reservations, so please call the Tasting Room to reserve your spots! (541) 776-2315, Option 1

We encourage you to come a little early to settle in to your seats, order food, grab your drinks, and get ready to dance the night away!

MUSIC + WINE SERIES FEATURING The Fret Drifters****CANCELED****
2026-07-03 18:00 - 20:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Unfortunately, there was a mix-up with the Fret Drifters and they doubled booked themselves. Therefore, music for Friday, July 3rd has been canceled. Happy 4th of July!!

MUSIC + WINE SERIES FEATURING Case Watson
2026-07-05 16:00 - 18:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Case is a vocalist, songwriter, & producer. Join us at RoxyAnn Winery for a Sunday afternoon of music and fun in the tasting room!

Listen to live music while sipping on some delicious & award-winning wines, or crisp & refreshing beer from the tap: grab all your friends and make a night of it!This event is FREE but we are taking reservations, so please call the Tasting Room to reserve your spots! (541) 776-2315, Option 1.

We encourage you to come a little early to settle in to your seats, order food, grab your drinks, and get ready to dance the night away!

MUSIC + WINE SERIES FEATURING Pozitronics
2026-07-10 18:00 - 20:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
The Pozitronics are southern Oregon’s premier “all-you-can-dance” band playing a unique mix of classic rock, R&B, and funk, with love, positive vibes, and a whole lot of energy. You bring the dance moves, we bring the music.

Listen to live dance-worthy music while sipping on some delicious & award-winning wines, or crisp & refreshing beer from the tap. Grab all your friends and make a night of it!

This event is free, but we are taking reservations so please call the Tasting Room to reserve your spot! (541) 776-2315, Option 1.
We encourage you to come a little early to settle in to your seats, order food, grab your drinks, and get ready to dance the night away!

FREE MUSIC + WINE SERIES FEATURING Encore 5
2026-07-12 18:00 - 20:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Encore 5 has a mission to provide quality, heart-felt music entertainment delivered in a professional manner.
Join us to listen to amazing music while sipping on some delicious & award-winning wines, or crisp & refreshing beer from the tap! Make a night of it and grab some dinner from our on-site food trucks or our light plated menu in the tasting room.
This event is FREE but we are taking reservations so call the Tasting Room to reserve your seats now at (541) 776-2315, Option 1
We encourage you to come a little early to settle in, order food, grab your drinks, and get ready to dance the night away!

Family Night!🎉
2026-07-14 17:00 - 19:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Join us for an evening of family fun at the winery. We’ll have family-friendly food options, bounce house entertainment for the kids and of course delicious wines and beer on tap for the adults.
FREE to attend. Join us for Family Night one Tuesday each month all summer long!

Comedy: Fine Wines & Punch Lines (Third Wednesdays)
2026-07-15 19:00 - 21:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Join us for a monthly Comedy Night, Age 18+ only: Fine Wines & Punch Lines!
$20 per person, please text Kendyl for tickets at 541-414-8050
Grab a glass of wine or one of our many other beverage choices and settle in for an evening of laughs. Third Wednesday of every month. Brought to you by Bisky Pop Productions.

Sip & Paint Pottery Party with Benjamin!
2026-07-16 15:00 - 17:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Grab your bestie and join us for an artsy night of drinks, fun and creativity!

Benjamin, your fearless leader for the evening, will guide you with the basics and then the design is up to you! Unleash your inner artist and take home a gorgeous piece of functional art.

Delicious wine and charcuterie pairings are also served in the tasting room, so come ready to enjoy some fabulous drinks, good food, and pottery fun!

To make reservations please visit the link: https://www.roguestoneware.com/shop/sipandpaintpottery/8

* Ticket price includes mug, paint/sgraffito supplies & workshop with Benjamin. Drinks sold separately.

MUSIC & WINE SERIES FEATURING Vinyl Tap
2026-07-17 18:00 - 20:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Southern Oregon’s premier Power Trio. Performing the best music ever released on vinyl. Rock and Roll you all know and love infused with jams that make you groove and elevate your soul.
Join us at RoxyAnn Winery for a Sunday afternoon of dancing and fun as we welcome Vinyl Tap to the tasting room! Listen to live music while sipping on some delicious & award-winning wines, or crisp & refreshing beer from the tap: grab all your friends and make a night of it!
This event is FREE but we are taking reservations, so please call the Tasting Room to reserve your spots! (541) 776-2315, Option 1

We encourage you to come a little early to settle in to your seats, order food, grab your drinks, and get ready to dance the night away!

FREE MUSIC + WINE SERIES FEATURING Tres Palomas
2026-07-19 16:00 - 18:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Tres Palomas plays Bossa Nova and international classics. The trio – Mari Simone on vocals, Sean Chon on upright bass, and Jason Wolverton on guitar – performs in Portuguese, Spanish, French, and English. Their sound carries the feeling of a trip abroad – unhurried and far from home.
Join us for a relaxing Sunday afternoon: listen to amazing music while sipping on some delicious & award-winning wines, or crisp & refreshing beer from the tap! Make a night of it and grab some dinner from our on-site food trucks or our light plated menu in the tasting room.
This event is FREE but we are taking reservations so call the Tasting Room to reserve your seats now at (541) 776-2315, Option 1
We encourage you to come a little early to settle in, order food, grab your drinks, and get ready to dance the night away!

MUSIC + WINE SERIES FEATURING Saucy
2026-07-24 18:00 - 20:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Saucy, a renowned local Southern Oregon musical group, joins us at RoxyAnn Winery for a Friday night of dancing and fun! Listen to some songs while sipping on some delicious & award-winning wines, or crisp & refreshing beer from the tap!

There is no cover charge for this event, so grab all your friends and make a night of it! This event is FREE but we are taking reservations so call the Tasting Room to reserve your seats! (541) 776-2315, Option 1

We encourage you to come a little early to settle in to your seats, order food, grab your drinks, and get ready to dance the night away!

MUSIC + WINE SERIES FEATURING Two of a Kind
2026-07-26 16:00 - 18:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Two of a Kind is a Rogue Valley acoustic duet featuring John Dickerson (of Honeypot) & Bridget Best. They’re bringing a fun mix of classic rock favorite and an easygoing vibe. Join us at RoxyAnn Winery for a Sunday afternoon of music and fun in the tasting room!

Listen to live music while sipping on some delicious & award-winning wines, or crisp & refreshing beer from the tap: grab all your friends and make a night of it!This event is FREE but we are taking reservations, so please call the Tasting Room to reserve your spots! (541) 776-2315, Option 1.

We encourage you to come a little early to settle in to your seats, order food, grab your drinks, and get ready to dance the night away!

MUSIC + WINE SERIES FEATURING Brisbane Project
2026-07-31 18:00 - 20:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Join us at RoxyAnn Winery for a Friday night of dancing and fun as we welcome Southern Oregon’s Brisbane Project to the tasting room!

The Brisbane Project, is a powerhouse trio of soulful blues, known for its authentic sound and captivating performances. This group of talented musicians has become a staple in the local music scene, drawing on a rich tradition of blues while infusing their own unique flair into each performance.

Listen to live dance-worthy music while sipping on some delicious & award-winning wines, or crisp & refreshing beer from the tap. Grab all your friends and make a night of it!

This event is free, but we are taking reservations so please call the Tasting Room to reserve your spot! (541) 776-2315, Option 1.
We encourage you to come a little early to settle in to your seats, order food, grab your drinks, and get ready to dance the night away!
