On Sunday afternoon, Elbow Room Taiko Drummers will open the second annual Hot Dogs & Cold Hops A Street Block Party in the Railroad District at 4 p.m. Mountaintop Sound follows with Americana and bluegrass. A Street's own Tlalli is making shucos, a Guatemalan street hot dog topped with avocado and curtido. West Coast Hot Dogs, Tale of the Dog and Pistola's are handling the more familiar versions. The block party started last year from a conversation between Wild Thyme Productions and Wellness Pet Supplies, and hundreds of people came, many with dogs in Halloween costumes.
"A Street and Ashland's Railroad District have their own character: a little gritty, unpretentious and warm — very local and away from more touristy parts of town." — Karolina Lavagnino, Wild Thyme Productions
That quote fits the next eight weeks. The Oregon Shakespeare Festival closes its season on the Angus Bowmer stage this month, and Ashland's fall calendar keeps going in smaller venues: the Armory on Oak Street, SOU's Main Stage, the Cabaret on Hargadine, a chairlift on Mt. Ashland, and then the covered rink across from Lithia Park. Here is the order, from now to the end of November:
- Oct. 4: A Street Block Party, Railroad District
- Oct. 8–11: Ashland Mystery Fest, with the Historic Ashland Armory as its hub
- Oct. 9–11: Mt. Ashland's Haunting and Chairlift Trick-or-Treat
- Oct. 14–18: Ashland New Plays Festival at SOU's Main Stage Theatre
- Oct. 24–25: OSF's final performances at the Angus Bowmer Theatre
- Oct. 31–Nov. 1: Children's Halloween Celebration, then a pop-up roller rink at the ice rink
- Nov. 8: Last performance of "Dracula: A Comedy of Terrors" at Oregon Cabaret Theatre
- November: Ashland Rotary Centennial Ice Rink opens for the 2026–27 season
- Nov. 27: Festival of Light and the Grand Illumination
The Weekend of Oct. 9 Is the Busiest Stretch
The fourth annual Ashland Mystery Fest runs Oct. 8–11. This year it has 15 cozy-mystery authors, two audiobook narrators, more than 60 events and more than 50 participating businesses and organizations. It started downtown. Ellie Alexander and Pam Hammond of Paddington Station came up with the idea, then brought it to Travel Ashland and the Ashland Chamber of Commerce. Travel Ashland director Katharine Cato led the work from there.
Thursday is a good day to dip in without buying a full pass. Paddington Station at 125 E. Main St. hosts a Test Kitchen Meet and Greet with Ellie Alexander from 10:30 a.m. to noon, with tickets sold through the store. The welcome reception runs from 4 to 6 p.m. at the Historic Ashland Armory, 208 Oak St., and is included in the Event Registration Package. The festival schedule also lists the 8 p.m. performance of "Dracula" at Oregon Cabaret Theatre that night.
On Friday and Saturday, the Armory hosts seven author panels. One of them, "How to Survive Your Stay in a Cozy Village," brings together moderator Tiffany Gullion-Krieg with Michelle Chouinard, Esme Addison, Mia Manansala and Catherine Bruns. In the evenings, Ashland Springs Hotel holds two ticketed dinners:
- "Mrs. Henderson is Dead," a four-course immersive mystery dinner on Oct. 9 or 10. Doors open at 6 p.m. in the Crystal Room, and tickets are $95 per guest plus a checkout fee.
- The Masquerade Dinner on Oct. 10. Doors open at 6:15 p.m. in the Grand Ballroom, tickets are $75 per guest plus a checkout fee, and mystery authors lead a group reading and reveal.
As of Travel Ashland's Oct. 1 update, package bundles and Friday and Saturday day passes were still on sale until sold out. That may have changed since.
The same weekend, Mt. Ashland runs its own events. "A Haunting on Mt. Ashland" takes place Oct. 9 and 10, with evening time slots from 7 to 10 p.m. Each slot includes a chairlift ride and a haunted trail. The family version, Chairlift Trick-or-Treat, runs Oct. 10 and 11, with a costumed chairlift ride, treats and a haunted-trail walk in daylight. Families who would rather not ride in the dark have that second option.
Four New Scripts at SOU, Each Read Twice
The Ashland New Plays Festival follows the next week. It presents staged readings of its four winning scripts at SOU's Main Stage Theatre, 491 S. Mountain Ave., Oct. 14–18. Each play gets one evening reading and one matinee, so a weekday conflict doesn't mean missing a script:
| Play | Evening, 7:30 p.m. | Matinee, 1:30 p.m. |
|---|---|---|
| "Netta and Ru" by Lisa Langford | Wed., Oct. 14 | Sat., Oct. 17 |
| "persian girl play" | Fri., Oct. 16 | Thu., Oct. 15 |
| "Threshold" | Thu., Oct. 15 | Sun., Oct. 18 |
| "The Caelumids" | Sat., Oct. 17 | Fri., Oct. 16 |
These are readings of scripts that haven't been fully staged yet. For anyone who has seen OSF's full productions this season, that makes the festival a very different kind of night out.
The Bowmer's Last Weekend, and the Cabaret Show That Runs Past It
OSF's two remaining productions both play the Angus Bowmer Theatre. "Come From Away," directed by Laurie Woolery, ends Oct. 24. "A Midsummer Night's Dream," directed by Marcela Lorca, ends Oct. 25. That is the last date on OSF's 2026 season listing. Both have run since mid-March, so these are the last chances for anyone who kept meaning to go.
Oregon Cabaret Theatre's "Dracula: A Comedy of Terrors" keeps going for two more weeks, through Sunday, Nov. 8. Ashland.news lists 1 p.m. matinees on Thursday, Saturday and Sunday, plus 8 p.m. shows on Wednesday, Thursday, Friday, Saturday and Monday. After OSF closes, it is the main Halloween-season show still running in town, and it plays at 241 Hargadine St., a short walk from the Bowmer.
Halloween Ends at the Rink
The Ashland Chamber's Children's Halloween Celebration falls on a Saturday this year, Oct. 31. Children and parents line up at Gresham and E. Main, and the procession starts at about 3:45 p.m. Everyone else in costume lines up behind them. Rogue Samba plays on the Plaza, and the Witches dance in front of Treehouse Books. Businesses with a pumpkin in the window hand out candy.
At 5:30 p.m., after the parade, a pop-up roller-skating rink opens at the Lithia Park ice rink and stays through Sunday. The Chamber says to check with the Parks & Recreation Department for details. The rink is at 95 Winburn Way, across from Lithia Park. Roller skates on Halloween weekend come before the ice for the rest of the season.
The Rink Carries the Calendar Into Winter
The City's Oct. 2 e-newsletter says crews have installed a snow-load kit on the cover of the Ashland Rotary Centennial Ice Rink and are improving the hard surface and electrical systems. The City says the rink will open in November for the 2026–27 season but hasn't announced an exact date. Updates will be posted at ashlandoregon.gov/IceRink.
Downtown, the Festival of Light falls on Friday, Nov. 27, the day after Thanksgiving. The Chamber lists Plaza festivities starting at 3 p.m. and Santa's procession at 5 p.m., followed by the Grand Illumination. Travel Ashland's listing, posted in March, runs the event from 2 to 9 p.m. Plan around the 5 p.m. procession and check the start time with organizers closer to the date.
Mt. Ashland has changes ahead for winter too. Rachel Canada started as general manager on Sept. 1 and oversees operations year-round. The Windsor Chairlift replacement has been pushed to spring 2027 because the money wasn't raised in time for a 2026 replacement. The existing lifts will stay in service until then. 2026–27 season passes are on sale, but the resort hasn't posted an opening day.
One New Name Downtown
CO WORK // CO PLAY, a café and contemporary dining space at 82 North Main Street, is running the beer garden at Sunday's A Street party. Zahara Cullumbine is the owner and beverage director, and Dane Murray is the executive chef. For now it serves evenings only. The website says morning service will start "soon" but gives no date. Its evening hours fit a fall calendar that keeps going into November.
If your fall plans in Ashland have you thinking about how your home works for your daily life, Blue Mountain Group can help you sort out what to do next, whether that means staying put, making changes or getting ready to move. Schedule your free consultation, and we'll walk you through it step by step.
