Date night ideas in Medford, OR

Free weekly trivia night with prizes plus cocktails, local beer, wine and food available. Bring a team and test your knowledge.

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.

Screening of a coming-of-age documentary by Paige Bethmann, followed by discussion. A chance to see a new regional film work on the big screen.

Live sets from Fox and Bones and Foxtail for an evening of indie/rock music. Expect a typical small-venue concert atmosphere.

Synopsis: Montgomery, Alabama, 1955. Ruby, a hoodoo practitioner and sex worker, has been unable to access her magic since burying her mother a year ago. When her devout, socially ambitious play-sister Netta gets engaged, their bond is tested by more than faith versus folk tradition.

A fast, 90-minute comedic take on Dracula with broad physical comedy and adult themes. Laughs and theatrical thrills in equal measure.

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

Second session in a three-part creative writing series focused on using the five senses to bring scenes to life. For adult writers seeking craft-focused exercises.

Guided pottery painting with step-by-step help, drinks, and a relaxed social atmosphere. Leave with a finished 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.

Evening bingo with cash prizes; doors open early and attendees may bring their own food. Casual, social game night for seniors.

Evening sports-card trading with local vendors, collectors, food specials and Thursday Night Football on-screen. Good for hobbyists and shoppers.

Meet other locals over a meal at a rotating restaurant and support a local cause. Casual networking with a give-back component.

An evening of music and storytelling celebrating George Harrison’s life and songs performed on the Camelot stage.

Synopsis: Respected appellate judge and Holocaust scholar David Lewin nears the end of his life, slipping in a morphine haze between the present and ghostly visits from his parents in their younger forms, fleeing Nazi Germany and Lithuania in the late 1930s.

Synopsis: In a small town outside of New York City, a tight-knit group of Iranian teenagers comes together over the course of a spring semester to do normal teenage things: fall in love, read fortunes in coffee, and complain about their “vay, vay, vay” Persian parents.

A darkly comic Gothic romance about two reclusive sisters, exploring isolation, desire and manipulation on the moors.

A touring adult variety show delivering high-energy performances and theatrical spectacle. Expect dancing, production numbers and an adult atmosphere.

A rotating lineup of stand-up comedians in an intimate lounge with cocktails and small bites. Expect an evening of laughs and local talent.

Live performance by Analog Dog with Balladir opening. Expect a night of original music in an intimate club setting.

Open-mic karaoke hosted by DJ Breezy with happy hour beforehand. Sing along or enjoy the show in a lively club atmosphere.

A high-energy Thursday night with a party atmosphere and crowd-driven antics. Expect a lively bar scene and late-night fun.

Weekly comedy open mic hosted by Jason Webb with music by Spud Dohm at Rocky Tonk Saloon. Sign-ups begin at 8 PM, and comics start at 8:30 PM. This event is for ages 21 and over.

Sign up to play or sit in with the house band for an open, late-night pub jam backed by the venue's regular rhythm section.

A big-band tribute program celebrating Frank Sinatra, performed by the Tommy Dorsey Orchestra with guest vocalist Hayden Grove.

Browse vendor booths, sample olive oils and vinegars, and enjoy live music at the Third Friday market. A family-friendly outdoor market vibe.

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.

Artists of the Applegate, a group exhibition featuring 21 artists from throughout Southern Oregon’s Applegate Valley, opens Friday, October 16, at Langford Art Gallery in Phoenix. Presented in collaboration with A Greater Applegate, the exhibition runs October 16 through November 21, 2026, with an opening reception, artist panel, and artist talk planned throughout the exhibition.

A tight local collective recreating the sophisticated grooves and arrangements inspired by Steely Dan's catalog.

Live classic rock while you sip RoxyAnn wines or beer in the tasting room. Free to attend; reservations encouraged for seating.

Final season of a long-running haunted attraction featuring immersive walkthrough scares, a cabaret lounge, food, drinks and live acts.

Monthly evening market celebrating local artisans, vintage sellers and live music, with food vendors and special birthday festivities.

Get Ready to Share Your Light! Join us at our ongoing Friday Open Mic night, a truly encouraging space where all voices and creative expressions are deeply welcome. Hosted by key community member Iósua Henryk Muineachán, this special gathering is designed to reinforce the beauty of the creative process—regardless of where you are in your journey.

Celebrate the Night Market’s first birthday with vendor booths, food options, and live music performances.

Solo piano recital by Sebastian Picht featuring a program of classical and possibly jazz-influenced works.

Synopsis: In a small town outside of New York City, a tight-knit group of Iranian teenagers comes together over the course of a spring semester to do normal teenage things: fall in love, read fortunes in coffee, and complain about their “vay, vay, vay” Persian parents.

A stage concert celebrating George Harrison’s music and life, featuring performances of his solo and Beatles-era songs.

A darkly comic Gothic play about two isolated sisters, exploring desire, manipulation and subverted romance.

Chadwick's Sports Bar & Pub hosts a comedy show featuring Ngaio Bealum, known for his storytelling and wit. Admission is $15, and attendees must be 21 or older.

Free monthly stand-up comedy show. 21+.

Two local bands performing post‑punk, dark wave and eclectic art/psychedelic rock. Cover charge $10.

Late‑night bar takeover with themed vibes and food and drink service into the early hours.

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

Official SOPride after-party featuring guest entertainer Cynthia Lee Fontaine. Expect drag performances and a lively celebration with the Pride crowd.

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.

An evening performance by singer-songwriter Scott Pemberton with live originals and covers.

A group dinner event featuring Kahlo Grill’s menu—expect shared plates and a social atmosphere.

Three bands bring a high-energy, all-ages rock show with debuting acts and established local favorites. Advance and door tickets available.

Synopsis: Blythe and Thora sit on Blythe’s porch and talk about the future. Their grandsons, Eddie and Mitchell, stand in Blythe’s yard and talk about the past. And in between them all is the scary, unpredictable present that keeps them rooted in place. Come be a part of the creative process as this new play comes to life through the magic of a dramatic reading.

A stage tribute exploring George Harrison’s music and life, performed live at the theatre. A must-see for Beatles and solo-era fans.

Monthly West Coast Swing social with a lesson first. $15.

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

YAARO Light performs live, with DJ Ghoulian closing the night.

A seated harvest dinner in the barrel room with seasonal dishes and paired RoxyAnn wines. Limited seats; reservations recommended.

Local musicians take the stage for an open mic night welcoming performers and listeners of all skill levels.

Fire spinners and flow artists light up the Plaza every Sunday night. Free; donations welcome.

Watch Monday Night Football on a 100-inch HD screen while enjoying the game-night menu and bar service.

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

Teens meet to discuss plots, characters and themes with complimentary tea and snacks. Bring your thoughts and favorite moments to share.

Beginner two-step lessons covering basic footwork and partner connection; single-session and multi-class pricing available.

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

Team trivia night with prizes, cocktails, local beer, mocktails and food. Free to play—bring a crew and enjoy downtown Ashland trivia fun.

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

Monthly comedy night at the tasting room—age 18+. $10 admission; reserve by phone or online. Enjoy wine and stand-up.

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.

Monthly zine-making meetup led by a local artist—collage, ink, drawing and zine trades in a welcoming space. Beginners and trading encouraged.

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 free, Halloween-themed music bingo night with spooky hits and guilty pleasures. Bring friends for a playful, music-driven competition.

A high-energy punk/rock lineup featuring touring and local bands for an evening of loud live music.

Hosted pub trivia—bring a team and test your knowledge across rounds led by Casey. Expect a lively pace and pub atmosphere.

An evening presentation celebrating George Harrison’s music and life with live performance and storytelling on the Camelot stage.

A staged production of Jen Silverman’s darkly comic, gothic play with sharp wit and strange twists.

Open-mic karaoke night—sign up to sing crowd favorites or cheer on local performers.

Expect a raucous Thursday-night bar crowd with high-energy vibes and lots of local regulars.

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

Open jam backed by the house band—sign up to play or sit in with fellow musicians.

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.

An evening performance by MALINKA featuring live music in an intimate setting. Expect a full band set and crowd favorites.

Monthly open mic for original music, hosted by the Southern Oregon Songwriters Association.

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.

Ian George & the Knee Pockets are a subtly explosive and peculiarly adventurous band delivering the sort of concert you’ll likely dance, sway, sing, laugh and probably cry too. There is one motive: ALLOW A GOOD TIME The performance teems with whimsicality, clever arrangements – interrupted by triumphant tangents – and outlandish solos grounded by George’s emotive and gauzy voice and by the simple…

Get Ready to Share Your Light! Join us at our ongoing Friday Open Mic night, a truly encouraging space where all voices and creative expressions are deeply welcome. Hosted by key community member Iósua Henryk Muineachán, this special gathering is designed to reinforce the beauty of the creative process—regardless of where you are in your journey.

A live comedy showcase featuring local and touring comedians performing stand-up sets for a night of laughs.

A theatrical concert exploring George Harrison's music and life through performance and storytelling.

A stage production of Jen Silverman's dark comedy exploring family, isolation and unexpected twists.

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

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.

An evening of contemporary dance blending athleticism, humor and joyful ensemble work.

Live music featuring Fleet Drifters with special guest Jim Sitter; expect a lively bar show.

A staged musical tribute exploring George Harrison's songs and remarkable life story.

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

Afternoon jazz duet with Vanessa Finney; enjoy live vocals while sipping RoxyAnn wines or beer from the tap. Bring friends for a relaxed danceable set.

David & Phil perform a blues duo set featuring classic and original blues numbers.

Free monthly classical concert in downtown Medford. Donations welcome.

Live blues duo performing on the patio with a relaxed outdoor vibe and drinks available. Casual evening set ideal for music lovers.

Open mic night for musicians and listeners; sign up to play or come enjoy a variety of local acts. All levels welcome.

Fire spinners and flow artists light up the Plaza every Sunday night. Free; donations welcome.

Catch the game on a 100-inch HD screen with a full game menu in a lively bar setting. No cover usually required.

Learn about bats and sketch them during a nature-center drawing session for Bat Week. Materials or guidance provided.

When everything collapses at once, survival becomes an act of love. After Julie Akins‘s husband, Leo, suffers a devastating stroke, she becomes his caregiver, advocate, and lifeline. Then Julie’s own body begins to fail. A specialist raises the possibility of a slow-moving cancer, but no one provides a clear diagnosis or coordinated path forward.

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

An immersive performance using found objects, handmade instruments, electronics and spoken text to explore wrongful imprisonment, exoneration, and resilience.

Share work and get constructive feedback in a friendly group; all genres welcome but time may limit sharing.

A beginner-friendly series teaching the basics of the Night Club Two-Step; drop-in or sign up for the full session. Partner practice and friendly instruction.

Winner of the Pulitzer Prize, Michael Cristofer’s The Shadow Box is a moving and compassionate drama about love, mortality, and the strength of the human spirit. Set in a hospice setting, the play follows several families confronting life’s most profound questions with honesty, humor, and grace.

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

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.

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.

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

Monthly downtown night: shop specials, gallery openings, and artists and musicians in local businesses.

Free monthly stand-up comedy show. 21+.

Monthly West Coast Swing social with a lesson first. $15.

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.

The Ashland Gallery Association's monthly art walk: openings, artists on hand, and a map at ashlandgalleries.com.

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