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WINE & BEER TASTING IN MEDFORD, OR

Some of the Rogue Valley's finest boutique wineries can be found right here in Medford. Spend the day wine tasting through town, or venture out and experience the whole valley on one of our unique Southern Oregon Wine Trails. Check out our Medford Ale Trail for all the best places to try the local brew. 

OCTOBER
7
Allison & Victor @ DANCIN
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OCTOBER
8
Traditional Irish Music @ Dunbar Farms
Join us for our first live music performance of the year! A company of talented musicians jam with traditional Irish…
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OCTOBER
9
Doodlepalooza!
Doodle competitions, costume contests, awards & prizes plus great food and beer!
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OCTOBER
9
Jeff Kloetzel @ Dunbar Farms
Jeff Kloetzel blends steady acoustic rhythms with warm vocals and a thoughtful mix of originals and covers. His performances are…
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OCTOBER
9
John Jons @ Schmidt Family Vineyards
Join us on Friday, October 9th as we host live music featuring John Jons from 5pm to 8pm! John describes…
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OCTOBER
9
Mercy @ RoxyAnn Winery
Based in beautiful Southern Oregon, Mercy Featuring Lynda Day is one of the premier acts in the region. Attending…
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OCTOBER
9
Sonido Alegre Band @ Trium Wines
Enjoy music and hand crafted wines from the Rogue Valley!
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OCTOBER
10
Cathy Bolton Duo @ StoneRiver Vineyards
CATHY BOLTON DUO takes the stage from 5–7 PM for an evening of live music, wine and great company. And come…
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OCTOBER
10
Harvest Hayride & Winery Tours @ Schmidt Family Vineyards
Don’t miss our annual Harvest Hayride and Winery Tours on Saturday, October 10th, 2026 from 12pm to 4pm. Tours include…
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OCTOBER
10
Talent Maker City's 10 Year Anniversary Party
Ten years ago, Talent Maker City opened its doors with a simple idea: to create a place where people could…
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OCTOBER
10
The Have Nothings @ Dunbar Farms
Traveling all the way from Flagstaff Arizona, this duo have nothing but musical talent! This two-piece acoustic folk duo specialize in…
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OCTOBER
10
The Rogue Marathon
Second weekend in October! findmymarathon.com ranks this course as the FASTEST IN OREGON! We are looking forward to this fall…
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OCTOBER
11
Adam Gabriel @ Dos Mariposas
Adam Gabriel brings a powerful mix of rock, blues, and soul-driven songwriting. Known for his strong stage presence and meaningful…
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OCTOBER
11
Dennis Konecny @ RoxyAnn Winrey
Join us at RoxyAnn Winery for a Sunday afternoon of dancing and fun as we welcome Southern Oregon’s Dennis Konecny…
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OCTOBER
14
Fox & Bones and Foxtail @ The Copper Plank
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OCTOBER
15
Autumn Magic - Witch Bell Wreath & Decoupage Pumpkin Workshop
October 15 - Autumn Magic - Step into the beautiful surroundings of Paschal Winery for an enchanting evening of…
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OCTOBER
16
33 String Drive @ Dunbar Farms
33 String Drive is a six-piece Bluegrass/Americana band from Southern Oregon that includes fiddle, banjo, mandolin, guitar, Dobro and upright…
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OCTOBER
16
Deluxe @ RoxyAnn Winery
Classic rock & roll on demand! They play the hits! Listen to live dance-worthy music while sipping on some delicious &…
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OCTOBER
16
Forks & Friends Stroll
This ten-day culinary experience invites residents and visitors to explore the diverse flavors of Downtown Medford. Throughout the week, participating…
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OCTOBER
16
Jared Gutridge @ Schmidt Family Vineyards
Jared Gutridge is a Rogue Valley based acoustic singer/songwriters est. in 2013. https://www.facebook.com/Jaredgutridgemusic FREE live music 5-8pm Tasting room open noon-8pm Kitchen open…
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OCTOBER
16
Kristen & Robbie @ Trium Wines
Enjoy music and hand crafted wines from the Rogue Valley!
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OCTOBER
16
Steely Dean @ Dos Mariposas
Steely Dean returns to Dos Mariposas for new tune offerings and the same stellar performance SD fans have come to…
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OCTOBER
17
Bales & Ales @ Common Block Brewing
Head to the patio for an afternoon of pumpkin carving, corn hole, seasonal beers, fall food specials and live music…
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OCTOBER
17
Mercy Duo @ StoneRiver Vineyards
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OCTOBER
17
Murder Ballads @ Historic Orth House
Ready to get in the Halloween season? Mark your calendars for this evening of Murder Ballads at the Historic…
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OCTOBER
17
Pozitronics @ Apple Outlaw Ciderey
For the first time ever, The Pozitronics are bringing their funky, feel-good grooves to Apple Outlaw in the Applegate/Jacksonville area!…
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OCTOBER
17
The Fret Drifters @ Dunbar Farms
The Fret Drifters are an original band from Southern Oregon showcasing futuristic acoustic guitar. This event is family friendly and free…
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OCTOBER
21
Fine Wines & Punch Lines @ RoxyAnn Winery
Join us for a monthly Comedy Night, Age 18+ only: Fine Wines & Punch Lines! This event is $10 to attend.…
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OCTOBER
23
Jeff Kloetzel @ Trium Wines
Enjoy music and hand crafted wines from the Rogue Valley!
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OCTOBER
23
Malinka Live @ Dunbar Farms
High-vibe Eastern European folk and beyond with a modern flavor! Romani, Balkan, Slavic, Latin and original music, with groovy, funky…
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OCTOBER
24
Ghostly Affair Halloween Party
Come to the Historic Orth House for the costumes, live music, tarot card readings and more! $25 includes appetizers and…
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OCTOBER
24
Nick & Shae Live @ Dunbar Farms
The dynamic duo of Shae Celine and Nick Garrett-Powell, two of Southern Oregon's most prolific vocalists perform harmony arrangements of…
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OCTOBER
24
Soft E Experience @ Dunbar Farms
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OCTOBER
24
The Reverberays @ StoneRiver Vineyards
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OCTOBER
25
Vanessa Finney Jazz Duet @ RoxyAnn Winery
Vanessa is a singer based in Ashland, OR. Join us at RoxyAnn Winery for a Sunday afternoon of dancing and fun…
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OCTOBER
30
Femme Fatale @ Trium Wines
Enjoy music and handcrafted wines from the Rogue Valley!
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OCTOBER
30
Pozitronics RoxyAnn Halloween Party
Come dressed in your Halloween best and dance the night away with The Pozitronics! πŸ’ƒπŸ•ΊπŸŽΆ πŸ‘» COSTUME CONTEST + PRIZES! πŸ‘» So…
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OCTOBER
31
Halloweek All Day Party @ Rellik Winery
Join us for a hauntingly fun, all-day Halloween Bash at Rellik Winery! Celebrate the season with live music from Pozitronics…
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OCTOBER
31
Halloween Party with Robbie Dacosta Band
You ready for a rocking good time? Robbie Dacosta and his band will help us celebrate Halloween! Activities include: -Free live…
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OCTOBER
31
Spooky Vines & Vinyl @ Wooldridge Creek Vineyard
Get ready for a hauntingly good time! We'll have Halloween-themed vinyl spinning out on the crush pad, setting the mood…
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OCTOBER
31
The Pozitronics Padigan Halloween Show
We’re going out with a BOO! πŸ‘» Join The Pozitronics for our FINAL Halloween event of the season and Halloween Show…
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NOVEMBER
13
Steven Swift Solo @ Dunbar Farms
Steve will be sharing some really old and extremely new tunes! Who knows who will join him on stage! It's…
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NOVEMBER
21
Applegate Valley Uncorked Barrel Tour
Come celebrate growing season with a self-guided tour of the Applegate Valley Wine Country. Fall is the perfect time to…
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NOVEMBER
22
Tres Palomas @ RoxyAnn Winery
Tres Palomas plays Bossa Nova and international classics. The trio – Mari Simone on vocals, Sean Chon on upright bass,…
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NOVEMBER
29
Wreath Making @ Wooldridge Creek Vineyard
Led by friend of the winery, Stacey Denton. Take a step by step guided class and go home with your very…
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