The Wine Walk Is Back in Sierra Madre, and It Helps Pay for the Rest of Your Fall Calendar

"The Sierra Madre Wine Walk is BACK!" That's how the Chamber of Commerce calendar announces it, and it credits the return after "a long hiatus" to the Sierra Madre Community Foundation. Pasadena Now puts a number on that hiatus: 12 years.

The headline is a good evening out on Saturday, October 10. The detail worth reading sits further down the ticket page. The Foundation lists the causes it has backed for 26 years: the library, local schools, "the Halloween happenings," art programs, the Mount Wilson Trail Race, the Rose float, Search and Rescue, and Sierra Madre Little League. It says every dollar raised stays in town. Look at the village calendar for October and November and many of those names show up again. The Wine Walk opens the season, and it also helps pay for the season that follows.

October 10, Downtown

The details, from the event's ticket page and Pasadena Now's listing:

• When: Saturday, October 10, 2026, 5:00 to 8:00 p.m.
• Where: Downtown Sierra Madre, along Sierra Madre Blvd.
• Cost: $50 presale general admission, or $65 at the door while day-of tickets last
• Included: a Wine Walk glass to keep and 10 tasting tickets you can use at participating businesses
• Ages: 21 and over, with one ticket per person

Twenty-two local small businesses are taking part, pouring "curated selections from local wineries and distributors." Ten pours across 22 stops means choosing where to go, and that suits the event's full name, Sip, Shop & Stroll. The full list of businesses wasn't posted publicly when we checked. One stop is confirmed: Big Love Animal Rescue will set up in the courtyard of RT Rogers Brewing Co. at 38 E. Montecito Ave. Tickets are sold through the Foundation's Wine Walk page. You can read more about the organization at sierramadrefoundation.org.

Three Weeks Later, the Same Downtown Turns Orange

The Foundation lists "the Halloween happenings" among the things it supports, and Sierra Madre's Halloween lasts most of the month.

It starts in storefront windows. The Sierra Madre Civic Club is hosting the Downtown Halloween Window Painting again, from October 14 through October 31. It's free for local youth artists, and applications are due October 16 at sierramadrecivicclub.org. Some of those windows will likely belong to businesses that poured wine on October 10, though no published list confirms which ones.

On Saturday, October 31, the day runs in two parts:

1. Sierra Madre's Hometown Halloween Festival at Memorial Park. Expect a free pumpkin patch, trunk-or-treat on Hermosa Avenue, live music from The Skinny Ties, a performance by Sierra Madre Dance Center, a Kid Spook Zone, face painting and a caricature artist, a themed photo booth, and food vendors. The listing's description says 10:00 a.m. to 2:00 p.m., but the calendar heading for the same event says noon to 2:00 p.m. Check with the organizer before you plan the morning around it.
2. Downtown Trick or Treating, 2:00 to 5:00 p.m. at participating Sierra Madre businesses. It picks up right where the festival leaves off. Businesses that want to be a stop can sign up by emailing [email protected].

Halloween falls on a Saturday this year, so families can go from the park straight downtown without fitting it around a school night.

The Library Fills In the Weeknights

The library is also on the Foundation's list, and its updated September and October calendar, revised September 15, fills the quieter evenings between the two big weekends:

Music & Mindfulness ends hours before the Wine Walk begins on October 10, so you can do both. Plan around the library's posted holiday closures too: Wednesday, November 11, and Thursday through Saturday, November 26 to 28.

The Race the Foundation Funds Is Back on Its Own Trail

The Mount Wilson Trail Race is the clearest example of what community money supports here, because one year ago it couldn't use its own mountain.

After the January 2025 Eaton Fire, fire and rain damage and a Forest Service closure took the trail out of service. Organizers moved the race to city streets and held the MWT 5K Recovery Run/Race/Walk on October 4, 2025. The Pasadena Star-News reported that hundreds took part.

That was exactly one year ago today. Since then the trail has reopened. The Forest Service closure order that took effect January 7, 2026 doesn't list the Mount Wilson Trail among its closed trails, though it still closes the Mount Wilson Toll Road below the trail. The full race came back on Saturday, May 23, 2026, on its 8.6-mile round-trip course from Kersting Court to Orchard Camp. The official race site reports 325 finishers. Before the race, the Star-News credited volunteer trail repairs with making that return possible.

The Other Canyon Is Still Waiting

Here's where each Sierra Madre trailhead stands this weekend:

Bailey Canyon's closure stands out because the city's restoration work there is done. The City received a $200,000 RPOSD RESTORE grant after the Eaton Fire and, after review, split it into $175,000 for Bailey Canyon and $25,000 for Mount Wilson. In July 2026 the Los Angeles Conservation Corps removed invasive plants, built about 2,072 square feet of bioswales, trimmed nine trees, and placed rock for stabilization. As of the project page's August 2026 update, fieldwork is complete and grant closeout is in progress. No reopening date has been announced, and both the City and the County still ask hikers to stay off Bailey Canyon's trails. For now, the Mount Wilson Trail is the one to use.

November Keeps the Same Venues Busy

The season doesn't end on October 31. Many of the same places host the next round:

• Fall Community Yard Sale: Saturday, November 7, 8:00 a.m. to 1:00 p.m., at Memorial Park, 222 W. Sierra Madre Blvd., the park that hosts the Halloween festival a week earlier.
• Shop Sierra Madre Winter Festival: Saturday, November 28, 8:00 a.m. to 5:00 p.m., with an artisan marketplace, community booths, live music, and a snow-sledding hill.
• Bob Baker's Nutcracker at Sierra Madre Playhouse, November 28 and 29, with 10:30 a.m. and 1:30 p.m. shows both days and an extra 4:30 p.m. show on the 28th.

If you'd like a show before then, the Playhouse has Outside Mullingar this weekend and next, with a performance today, Sunday, October 4, followed by Friday, October 9 at 8:00 p.m. and Saturday, October 10 at 2:00 p.m. The Saturday matinee lets out in time for the Wine Walk, which is about as close as Sierra Madre comes to a double feature.

So your $50 ticket on October 10 buys an evening of pours, and it also goes toward the Halloween events at the end of the month and the trail race in May.

If you're curious how the village's traditions and trail access fit into the value of a Sierra Madre home, Kate Amsbry is glad to talk it through over coffee downtown. Request your complimentary home consultation, and we'll start with what's on this fall's calendar.