Food and drink events in Medford, OR

DEATH AND THE MAIDEN, directed by Caroline Shaffer, and featuring Nell Geisslinger, Daniel Molina, and Jamie Newcomb, is a gripping exploration of justice, memory, and regret, challenging us to confront the moral ambiguities of revenge and forgiveness.

Join us every Wednesday Night for Trivia at Liquid Lounge in downtown Ashland! Gather your crew, grab a drink, and put your knowledge to the test with a fun night of trivia, prizes, cocktails, Oregon wine, local beer, mocktails, and food Trivia runs from 6–8 PM and is free to play!

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.

Team trivia downtown, then the Comedy Lab open mic takes the stage at 8.

Local comics try new material; sign up at 6:15 for a spot.

Krank It Up Karaoke with KJs Li'l Bit and The Great Martini, two nights a week by Ashland Creek.

Rogue Valley Growers & Crafters Market in Medford: farm produce, baked goods, flowers and handmade goods.

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.

Thursday nights at Resistance: rotating wine tastings, trivia, and food experiences: pasta-making nights, pizza parties, cook-offs, and more. Come as a couple, come alone, come with whoever you’re trying to impress. Free; all ages until 9 PM, 21+ to drink.

A company of local musicians jams traditional Irish and Celtic tunes in the tasting room. Family friendly and free.

Join us every Third Thursday for a night of laughs at Liquid Lounge in downtown Ashland! Third Thursday Comedy brings a rotating lineup of talented comedians to our intimate lounge for a fun night of stand-up, cocktails, local wine, beer, mocktails, and small bites.

Weekly comedy open mic hosted by Jason Webb in downtown Medford.

Dates: Friday, October 16 & Saturday, October 17, 2026 Doors: 6:30 PM Show: 7:30 PM Venue: The Stardust Lounge at Ashland Hills Hotel & Suites Address: 2525 Ashland St., Ashland, OR Tickets: $25 Age: 21+ Food & Drinks: Luna Cafe Additional: Limited VIP Meet & Greet and weekend hotel packages available.

Hop-on, hop-off trolley between Jacksonville-area tasting rooms. $30 day pass, $45 three-day, $15 happy-hour pass after 3 PM.

Join us at Pioneer Village Independent & Assisted Living for an afternoon of local flavors and good company! Sample tastings from local restaurants and wineries, mingle with friends and neighbors, and enjoy a taste of what Jacksonville has to offer. 805 N 5th St. | Jacksonville, OR 97530 FRI. OCT. 16th 1-3 PM Attend and Enter to Win Our Cozy Fall Basket Giveaway!

Ashland’s Friday night just got tastier. Imagine this: It’s the end of the week, your shoulders are finally down, and you’re eyeing something delicious — and maybe just a little indulgent. That’s where we come in. Welcome to Woodfired Pies & Vines, every Friday at Resistance Wine Co. Featuring Allium Wood Fired Pizza paired with wines that actually know what they’re doing.

Classic rock & roll on demand! They play the hits! 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!

Touring and regional stand-up every weekend. $15, 21+.

Free monthly stand-up comedy show. 21+.

Dates: Friday, October 16 & Saturday, October 17, 2026 Doors: 6:30 PM Show: 7:30 PM Venue: The Stardust Lounge at Ashland Hills Hotel & Suites Address: 2525 Ashland St., Ashland, OR Tickets: $25 Age: 21+ Food & Drinks: Luna Cafe Additional: Limited VIP Meet & Greet and weekend hotel packages available.

Rogue Valley Growers & Crafters Saturday market between Main St and Lithia Way.

Soup Stroll October 17 @ 11:00 am - 2:00 pm Warm up with Jacksonville’s newest culinary tradition: the Soup Stroll , happening Saturday, October 17th from 11am–2pm . Local shops and restaurants will serve creative one ounce tastings of homemade soups—250 tickets available at the Odd Fellows, 3 gallons per contestant, and a whole lot of fun. Stroll, sip, shop, and vote for your favorite.

Hop-on, hop-off trolley between Jacksonville-area tasting rooms. $30 day pass, $45 three-day, $15 happy-hour pass after 3 PM.

@ Davis’s Chair-Our mission is to enrich the lives of mobility-impaired people with independence and freedom by empowering them to engage in outdoor activities they previously were unable to, free of charge. It’s 5 O’Clock Somewhere…. This is our annual FUNdraising Dinner and Auction brought to you by Ko Kwel Casino Resort, in Medford OR.

Saturday happy-hour set from the house band before the night's headliners.

Jazz standards from the Great American Songbook (Ella Fitzgerald, Julie London, Peggy Lee, Billie Holiday), sung among the barrels. Calysta trained for nearly two decades with Ashland vocal coach Ken Orsow and studied vocal jazz at Berklee. No cover; walk in, or reserve to be sure of a seat. All ages until 9 PM, 21+ to drink. Pizza from The Allium until 8.

Food event at Kahlo Exotic Grill. Check the venue for details.

Touring and regional stand-up every weekend. $15, 21+.

Pumpkin patch, corn maze and farm fun every fall weekend.

Hop-on, hop-off trolley between Jacksonville-area tasting rooms. $30 day pass, $45 three-day, $15 happy-hour pass after 3 PM.

Save the Date for our Annual Harvest Dinner! This is a chance for us to sit back and celebrate what our family winery is all about! Join us for a delicious gourmet meal in our barrel room. Experience perfectly paired RoxyAnn wines with seasonal, local dishes in an intimate and gorgeous setting.

Pumpkin patch, corn maze and farm fun every fall weekend.

Monday-night jazz standards from pianist Paul Schmeling's band in a downtown Ashland lounge.

Rogue Valley Growers & Crafters Market: local produce, bread, flowers, artisan food and crafts every Tuesday through the end of the outdoor season.

Brew up some chemistry fun at this Halloween themed science program. Everyone gets to make a magical potion to take home. Explore new interests with cool STEAM programs. Each session will explore a different topic in Science, Technology, Engineering, Arts, and Mathematics. Every first and third Tuesday of the month, unless otherwise indicated. Program is hosted in English.

Krank It Up Karaoke with KJs Li'l Bit and The Great Martini, two nights a week by Ashland Creek.

Bugs-R-Us will be here to discuss owls in the environment and the part they play in the food-web cycle. We then get hands-on with real owl pellets, playing detective with latex gloves, tweezers and magnifying glasses to find out what the owls have eaten. This program will include hands-on time with a taxidermied barn-owl and owl calls.

Join us every Wednesday Night for Trivia at Liquid Lounge in downtown Ashland! Gather your crew, grab a drink, and put your knowledge to the test with a fun night of trivia, prizes, cocktails, Oregon wine, local beer, mocktails, and food Trivia runs from 6–8 PM and is free to play!

Team trivia downtown, then the Comedy Lab open mic takes the stage at 8.

Join us for a monthly Comedy Night, Age 18+ only: Fine Wines & Punch Lines! This event is $10 to attend. Please call the Tasting Room to make a reservation at (541) 776-2315, Option 1 or purchase online HERE. 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.

Local comics try new material; sign up at 6:15 for a spot.

Krank It Up Karaoke with KJs Li'l Bit and The Great Martini, two nights a week by Ashland Creek.

Rogue Valley Growers & Crafters Market in Medford: farm produce, baked goods, flowers and handmade goods.

Zines + Create=Fun Join us every 4th Thursday of the month from 5-7 p.m. at Art Bop Beer Co in Talent, Oregon for a fun zine-making social! Led by local artist ZinesbyZeph, express your stories through zine creation in a welcoming space. No experience is necessary. Bring zines to trade, make zines using collage, ink, drawing tools, etc. Beginners welcome.

Thursday nights at Resistance: rotating wine tastings, trivia, and food experiences: pasta-making nights, pizza parties, cook-offs, and more. Come as a couple, come alone, come with whoever you’re trying to impress. Free; all ages until 9 PM, 21+ to drink.

A company of local musicians jams traditional Irish and Celtic tunes in the tasting room. Family friendly and free.

Weekly comedy open mic hosted by Jason Webb in downtown Medford.

Hop-on, hop-off trolley between Jacksonville-area tasting rooms. $30 day pass, $45 three-day, $15 happy-hour pass after 3 PM.

Empty Bowls is an annual event to benefit food access in our community, including Uncle Food’s Diner and Food Angels. Attendees will have the opportunity to choose a unique, handcrafted ceramic bowl and have it filled with delicious soup provided by local restaurants.

Ashland’s Friday night just got tastier. Imagine this: It’s the end of the week, your shoulders are finally down, and you’re eyeing something delicious — and maybe just a little indulgent. That’s where we come in. Welcome to Woodfired Pies & Vines, every Friday at Resistance Wine Co. Featuring Allium Wood Fired Pizza paired with wines that actually know what they’re doing.

The RoxyAnn Open Mic Finale will be this Friday! The top 3 from the previous 8 month’s shows have won this paid date on a Friday Night at RoxyAnn! Here’s how it worked: We had a regular show every month and the 8 monthly winners* were featured in the semi-final September show, each playing 3 songs.

Touring and regional stand-up every weekend. $15, 21+.

Rogue Valley Growers & Crafters Saturday market between Main St and Lithia Way.

Hop-on, hop-off trolley between Jacksonville-area tasting rooms. $30 day pass, $45 three-day, $15 happy-hour pass after 3 PM.

Saturday happy-hour set from the house band before the night's headliners.

A jazz and cocktail-hour set the Saturday before Halloween, from a regular of Ashland’s live music scene. No cover; walk in, or reserve to be sure of a seat. All ages until 9 PM, 21+ to drink. Syrah, Malbec and Cab by the glass, flight or bottle; The Allium’s pizza until 8.

Touring and regional stand-up every weekend. $15, 21+.

Pumpkin patch, corn maze and farm fun every fall weekend.

Hop-on, hop-off trolley between Jacksonville-area tasting rooms. $30 day pass, $45 three-day, $15 happy-hour pass after 3 PM.

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!

Join us for a collaborative community event that brings together the SOU campus and the surrounding community! The event will feature booths hosted by SOU departments and community partners, each showcasing their work, sharing resources, and handing out candy. Food will also be available for purchase.

Pumpkin patch, corn maze and farm fun every fall weekend.

Monday-night jazz standards from pianist Paul Schmeling's band in a downtown Ashland lounge.

Rogue Valley Growers & Crafters Market: local produce, bread, flowers, artisan food and crafts every Tuesday through the end of the outdoor season.

Krank It Up Karaoke with KJs Li'l Bit and The Great Martini, two nights a week by Ashland Creek.

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.

Team trivia downtown, then the Comedy Lab open mic takes the stage at 8.

Local comics try new material; sign up at 6:15 for a spot.

Krank It Up Karaoke with KJs Li'l Bit and The Great Martini, two nights a week by Ashland Creek.

Fall market from Gather Production Co. with local makers, food and Halloween fun.

Open blues jam on the first and third Wednesdays. Bring an instrument or just listen. Free; donations welcome.

The Y's fundraiser party with dueling pianos.

An 18-piece big band swings through the standards on the second and fourth Wednesdays.

Touring immersive true-crime cocktail experience. Also Nov 14.

Open blues jam on the first and third Wednesdays. Bring an instrument or just listen. Free; donations welcome.

Free monthly stand-up comedy show. 21+.

Self-guided barrel-tasting tour of Applegate Valley wineries.

An 18-piece big band swings through the standards on the second and fourth Wednesdays.

Open blues jam on the first and third Wednesdays. Bring an instrument or just listen. Free; donations welcome.

An 18-piece big band swings through the standards on the second and fourth Wednesdays.