Musical Bingo
2026-04-22 18:00 - 20:00 (America/Los_Angeles) | 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 in the tasting room! 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. We encourage you to come a little early to settle in to your seats, order food and grab your drinks.

MUSIC + WINE SERIES FEATURING Shakedown
2026-04-24 18:00 - 20:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
ShakeDown is a Southern Oregon Classic Rock n Roll cover band that plays 70’s, 80’s to current classic rock tunes. Bill – Bass and lead vocals, Jason – Lead guitar and backing vocals, Leroy – Keyboards and backing vocals and Daryll – Drums, Ronnie – Lead Guitar and Lead Vocals.

Join us at RoxyAnn Winery for a Friday night of dancing and fun as we welcome Southern Oregon’s Shakedown to the tasting room! 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
2026-04-25 15:00 - 17:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
The RoxyAnn Open Mic will be on Saturday, April 25th, and we’ve come up with a way to make 2026 bigger and more exciting. Next 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.

Watercolor & Wine At RoxyAnn
2026-04-26 13:00 - 15:30, 2026-05-31 13:00 - 15:30 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Watercolor & Wine is back again for more watercolor adventures at the beautiful RoxyAnn Winery! All skill levels are welcome, and no experience is needed. So enlist your friends who would like to spend a relaxing afternoon painting and sipping wine.
The cost is $40 per person, which includes all necessary art supplies, plus a delicious glass of award-winning wine!
REGISTER NOW: Call (541) 702-7911

MUSIC + WINE SERIES FEATURING Kristen & Robbie Duo
2026-04-26 16:00 - 18:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Join us with talented Robbie Dacosta as he teams up with the incredible Kristen Calvin Gordon for a great evening of tunes from a variety of genres.
Join us at RoxyAnn Winery for a Sunday afternoon of 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!)
2026-04-27 16:00 - 19:00, 2026-05-04 16:00 - 19:00, 2026-05-11 16:00 - 19:00, 2026-05-18 16:00 - 19:00, 2026-05-25 16:00 - 19:00, 2026-06-01 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

Musical Bingo
2026-04-29 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 in the tasting room! 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 don’t be late; cards sell out fast!

MUSIC + WINE SERIES FEATURING Brisbane Project
2026-05-01 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!

FREE MUSIC + WINE SERIES FEATURING Tres Palomas
2026-05-03 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 Bingo
2026-05-06 18:00 - 20:00, 2026-05-13 18:00 - 20:00, 2026-05-27 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 in the tasting room! 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 Pozitronics
2026-05-08 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!

MUSIC + WINE SERIES FEATURING Connor Reese
2026-05-10 16:00 - 18:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Three-time Grammy Award watching singer/songwriter, Connor Reese, is here to bring you music, laughs, and maybe one too many historical references. Armed with only an acoustic guitar (and maybe a few plug ins on Logic Pro…), his unique brand of original comedy songs are sure to make you feel better about your life choices.

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!

Pups & Pours: Doggie Dash Demo
2026-05-15 10:00 - 14:00 | 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.

FREE MUSIC + WINE SERIES FEATURING Dr. Pain & The Remedy
2026-05-15 18:00 - 20:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Classic rock favorites featuring energetic power pop and more!

Join us for a fun-filled Friday night to kick off your weekend! Listen to some amazing music while sipping on delicious, award-winning wines. Or enjoy a crisp & refreshing beer from the tap! Make a whole 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!

Rick Millward Presents Open Mic
2026-05-16 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. Next 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 Rick Millward
2026-05-17 16:00 - 18:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Performing Singer/Songwriter/Producer & EMMY Nominated Composer.
Join us at RoxyAnn Winery for a Sunday afternoon of dancing 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!

Comedy: Fine Wines & Punch Lines (Third Wednesdays)
2026-05-20 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!
2026-05-21 17:00 - 19:00 | 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 Rogue Suspects
2026-05-22 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 Rogue Suspects! Members of the ensemble represent the region’s top vocal performers, music directors, actors, and dancers.

Grab all your friends and make a night of it! Tickets are $20. Call the Tasting Room to reserve your seats (541) 776-2315, Option 1 or purchase online HERE.

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 Nick Garrett-Powell
2026-05-24 16:00 - 18:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Join us at RoxyAnn Winery for a Sunday afternoon of dancing and fun as we welcome Southern Oregon’s Nick Garrett-Powell 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 Gunstock Red
2026-05-29 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 Gunstock Red to the tasting room!
Rock, Southern Rock, Country, Blues

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!

The event is $10 per person, please call the Tasting Room for Waitlist! (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 Dennis Konecny
2026-05-31 16:00 - 18:00 | RoxyAnn Winery, 3283 Hillcrest Rd, MEDFORD, Oregon, 97504, United States
Join us at RoxyAnn Winery for a Sunday afternoon of dancing and fun as we welcome Southern Oregon’s Dennis Konecny 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!
