Entertainment events in Ashland

Check out happening entertainment events all around Ashland, OR

Whitey Morgan and the 78's in Ashland

 Sat, 31 Jan at 07:00 pm Historic Ashland Armory

Winter Onesieland 2026 - 10 Years of Onesieland

 Sat, 07 Feb at 05:00 pm Downtown Ashland Oregon

Esmé Quartet Presented by Chamber Music Concerts

 Sat, 21 Feb at 07:30 pm SOU Music Recital Hall, 450 S. Mountain Avenue, Ashland, OR 97520-3239, United States

Skyler and The Sketchy Kids

 Sat, 07 Feb at 08:00 pm The Columbia Hotel USD 18 to 23

Moontricks

 Sat, 21 Feb at 04:00 pm Ashland Armory

Swan Lake | Ashland | January 20, 2026

 Tue, 20 Jan at 07:00 pm Oregon Center for the Arts at Southern Oregon University

Like A Rolling Band: The Stone House. Jeff Pevar & Inger Nova, Bret Levick & Friends

 Sat, 14 Feb at 07:00 pm OR-66, Ashland, OR 97520, United States

Tres Palomas @ Belle Fiore Winery

 Sat, 31 Jan at 05:30 pm Belle Fiore Estate & Winery

The Baltimore Consort: The Food of Love - at Chamber Music Concerts

 Fri, 30 Jan at 07:30 pm 450 S Mountain Ave, Ashland, OR 97520, United States

Trio Bohémo Presented by Chamber Music Concerts

 Sat, 28 Mar at 07:30 pm SOU Music Recital Hall, 450 S. Mountain Avenue, Ashland, OR 97520-3239, United States

The Pozitronics' Funky Disco VALENTINE'S Ball at Belle Fiore

 Sat, 14 Feb at 05:30 pm Belle Fiore Estate & Winery

Fat Chance Belly Dance® (FCBD®) Class in Ashland, Oregon.

 Sat, 07 Feb at 10:00 am Ashland Studio Z, 280 Hersey St. #1, Ashland, OR, United States, Oregon 97520

Madrone Trail's 19th Annual Benefit Auction

 Sat, 07 Mar at 05:30 pm Historic Ashland Armory

Holism, Healing and Mystical Experiences by Dr. Ian Luepker

 Tue, 27 Jan at 07:00 pm 1757 Ashland Street, Ashland, OR, United States, Oregon 97520

2nd Annual BASE Gala

Sat, 28 Feb at 06:00 pm Ashland Hills Hotel & Suites

Philip Reed(of The Brothers Reed) at Belle Fiore Winery

 Fri, 27 Feb at 05:00 pm Belle Fiore Estate & Winery

Phil Reed(of The Brothers Reed) at Local 31 Pub

 Thu, 12 Feb at 09:15 pm Local 31 Pub

Brisbane Duo - Belle Fiore

Fri, 13 Mar at 05:30 pm Belle Fiore Estate & Winery

Dinner and a show! John Ivey live at Callahan’s Mountain Lodge, Ashland 1.18.26

 Sun, 18 Jan at 05:00 pm Callahan's Mountain Lodge

A Closer Look at The Urantia Book: What It Is by Michael Hanna

 Tue, 03 Feb at 07:00 pm 1757 Ashland Street, Ashland, OR, United States, Oregon 97520

Ascension Ashlee's Sunday Tea Party

 Sun, 18 Jan at 03:33 pm North Mountain Park

RVML’s Annual Valentine's Day Party!

 Sat, 14 Feb at 06:00 pm 1757 Ashland Street, Ashland, OR, United States, Oregon 97520

Human Design Made Simple: The Science of Being You by Mari Smith

 Tue, 10 Feb at 07:00 pm 1757 Ashland Street, Ashland, OR, United States, Oregon 97520

Senior Living Roadmap: What You Need to Know and How to Plan and Navigate by Belinda Godin

 Tue, 20 Jan at 07:00 pm 1757 Ashland Street, Ashland, OR, United States, Oregon 97520

Ashland - Banff Mountain Film Festival

Sat, 07 Feb at 06:00 pm Sou Recital Hall

Phil Reed (of The Brothers Reed) at Liquid Lounge

 Thu, 05 Mar at 06:00 pm Liquid Lounge

Grace Before Sleep

 Sat, 07 Mar at 07:30 pm 450 S Mountain Ave, Ashland, OR 97520, United States

Tutunov Piano Series: Yoshio Hamano

 Fri, 13 Mar at 07:30 pm SOU Music Recital Hall, 450 S. Mountain Avenue, Ashland, Oregon

Free Film Series - PBS Preview of upcoming Ken Burns Documentary

 Sat, 24 Jan at 03:00 pm 1500 East Main Street, Ashland, OR, United States, Oregon 97520

LIFEFORCE METALFEST

 Sat, 25 Apr at 12:00 pm The Historic Ashland Armory

Tophouse in Ashland

 Sat, 28 Mar at 07:30 pm Historic Ashland Armory

Beats Antique

 Fri, 13 Feb at 04:00 am Ashland Armory

Better Together: Join Ashland’s 2026 Town Hall

Wed, 21 Jan at 05:30 pm 201 S Mountain Ave, Ashland, OR 97520-2165, United States

Belle Fiore Estate & Winery welcomes Jon Galfano in a solo show on Sunday, February 22nd at 5 p.m.

 Sun, 22 Feb at 05:00 pm Belle Fiore Estate & Winery

UNFINISHED: The Role of the Artist in the Age of Artificial Intelligence

 Mon, 19 Jan at 07:00 pm 290 East Main St, Ashland, OR, United States, Oregon 97520

2026 Wild & Scenic Film Festival

 Sat, 14 Mar at 05:00 pm Historic Ashland Armory

Plenty for All: The Art of Rick Fröberg

 Fri, 23 Jan at 06:30 pm 290 East Main St, Ashland, OR, United States, Oregon 97520

Aaron Reed(of The Brothers Reed) at Local 31 Pub

 Wed, 28 Jan at 07:00 pm Local 31 Pub

Speakeasy at 322

 Sat, 21 Mar at 06:00 pm Resistance Wine Company USD 10

Women With Wings Spring Concert

 Sat, 25 Apr at 03:00 pm First Presbyterian Church of Ashland

FREE - Honor Band Concert

 Sun, 15 Feb at 01:00 pm 491 S Mountain, Ashland, OR, United States, Oregon 97520

Zendo Activation Event

 Sat, 07 Feb at 12:00 pm 139 E Main St Free

Live Music - Late Night Show with Adam Gabriel

 Sat, 24 Jan at 08:00 pm 370 E Main St., Ashland, OR

SOswing Convention 2026: RING

 Thu, 14 May at 10:00 am Ashland Hills Hotel & Suites

Valentine's Day

Sat, 14 Feb at 04:30 am 7900 Hyatt Prairie Rd, Ashland, OR, United States, Oregon 97520

Southern Oregon Swing Out (SOSO) 2026

 Fri, 01 May at 02:00 pm Ashland Hills Hotel & Suites

Kitchen Dwellers in Ashland

 Wed, 15 Apr at 07:00 pm Historic Ashland Armory

MaryAnn Shank discusses her book “Sor Juana, My Beloved”

 Mon, 26 Jan at 07:00 pm 290 East Main St, Ashland, OR, United States, Oregon 97520

Winter of Rebellion Speakeasy and Comedy Nights

 Sat, 10 Jan Resistance Wine Company USD 25

TopHouse

 Sun, 29 Mar at 02:30 am Ashland Armory

Puzzling Adventures Scavenger Hunt - Ashland

 Thu, 25 Jun at 10:00 am Recommended Parking to Begin Adventure USD 38

Winter of Rebellion Speakeasy Jazz

Sat, 24 Jan Resistance Wine Company USD 25