Halloween Saturday in Sierra Madre: From Memorial Park to Downtown to After Dark

How long can one Halloween last in a town of Sierra Madre's size? This year, on Saturday, October 31, it runs from 10 a.m. to 10 p.m., with only one real break in those twelve hours.

The City runs the morning. The Sierra Madre Chamber of Commerce takes the afternoon. RT Rogers Brewing Co. has the night. For more than two weeks before all that, the Sierra Madre Civic Club has youth artists painting downtown storefront windows. None of these events overlaps another. The Chamber's own listing calls its afternoon event a way to keep the fun going "after the City's Hometown Halloween Festival." The schedule was built as a relay.

Here is how the day fits together, in order, and why the same pattern shows up again four weeks later.

The windows come first

Before any costume comes out, downtown is already dressed. The Sierra Madre Civic Club is "once again hosting" its Downtown Halloween Window Painting, which the club describes as "a fun, free tradition for local youth artists." The paintings stay up in downtown merchants' windows from October 14 through October 31.

Applications were due October 16, so the artists have already signed up. What's left is watching the windows change as the work goes up. Details and the program's background are on the Sierra Madre Civic Club website, and the Chamber posts the event on its window painting page.

The windows matter to the schedule because downtown is where the afternoon ends up. By 2 p.m. on the 31st, every trick-or-treater on the boulevard will walk past the finished paintings.

10 a.m. to 2 p.m.: the City's festival at Memorial Park

The day officially opens with Sierra Madre's Hometown Halloween Festival at Memorial Park and along Hermosa Avenue. It's free. The City organizes it through Sierra Madre Community Services. The full event description lists this lineup:

• A free pumpkin patch
• Trunk-or-treat on Hermosa Avenue
• Live music by The Skinny Ties
• A special performance by Sierra Madre Dance Center
• A Kid Spook Zone
• Face painting and a caricature artist
• A themed photo booth
• Food vendors

The listing also thanks "local businesses and nonprofit partners for helping make this event possible," and asks families to dress up.

About the start time: the header on the Chamber's festival page shows noon to 2 p.m. The event description on that same page says 10 a.m. to 2 p.m. So does the City's own September and October 2026 library calendar, which lists "Home Town Halloween Festival and Trunk-or-Treat" at Memorial Park from 10 a.m. to 2 p.m. Plan on 10 a.m.

The festival ends at 2 p.m., the same hour the next event begins.

2 to 5 p.m.: the handoff downtown

At 2 p.m. the Chamber takes over with Downtown Trick or Treating at participating Sierra Madre businesses, running until 5 p.m. The Chamber's listing spells out the connection:

Join us Saturday, October 31 from 2:00–5:00 PM and keep the Halloween fun going after the City's Hometown Halloween Festival.

The festival was designed as a morning. The trick-or-treating was designed to follow it. A family can go from the pumpkin patch at Memorial Park to the business district without a gap. The Chamber's flyer carries the line "Downtown Sierra Madre • Shop Local • Support Local," which tells you what the afternoon is for: getting festival crowds to the storefronts.

Businesses that want to be a trick-or-treat stop can sign up by emailing the Chamber at [email protected], which is listed on the Downtown Trick or Treating page. The Chamber hasn't published a list of participating storefronts yet. The surest way to find a stop on the day is to walk the business district and watch for the signs.

This is also the window paintings' biggest audience. The Civic Club's display runs through October 31, so the trick-or-treat crowd sees the youth artists' finished work on the paintings' last day.

7 to 10 p.m.: the grown-ups' turn on East Montecito Avenue

After 5 p.m., there's nothing on the schedule until 7. Then the day moves to the East Montecito Shopping & Arts District. RT Rogers Brewing Co., at 38 East Montecito Avenue, Unit #1, hosts a Halloween Party from 7 to 10 p.m. with "Festive Halloween Activities and a Grown-Up Costume Contest." The MCs are Matt Pawlik and Alex Wong.

According to the district's upcoming events page, no RSVP is needed. The taproom is open from noon to 10 p.m. that day, so it overlaps the whole afternoon too. You can find more about the brewery at RT Rogers Brewing Co.

That gives the day three hosts and three audiences: families at the park in the morning, shops downtown in the afternoon, and adults in costume at night.

The day at a glance

10 a.m. to 2 p.m. Hometown Halloween Festival and trunk-or-treat, Memorial Park and Hermosa Avenue. Run by the City through Sierra Madre Community Services.

2 to 5 p.m. Downtown Trick or Treating at participating businesses. Run by the Sierra Madre Chamber of Commerce.

All day, through October 31 Downtown Halloween Window Painting, Sierra Madre Civic Club.

7 to 10 p.m. Halloween Party and Grown-Up Costume Contest, RT Rogers Brewing Co., 38 East Montecito Avenue, Unit #1.

Before the 31st: smaller evenings around town

The run-up to Halloween is quieter, and most of it happens indoors. On Tuesday, October 27, the Sierra Madre Public Library hosts Adults at Play: Tabletop Game Night from 6 to 7 p.m. The City's calendar says to bring friends or come meet someone new. A selection of games will be there, or you can bring one to share. The program is for adults, and no registration is required.

Two days later, on Thursday, October 29, Fables and Fancies at 50 W. Sierra Madre Blvd. holds the last listed session of Introduction to Loose and Expressive Watercolor Painting, from 6:30 to 8 p.m. It's on the City of Sierra Madre events calendar, and Sumayya Ansari is the listed contact.

Neither event has a Halloween theme. Both are typical of how Sierra Madre's calendar runs between big days, with one small gathering per evening at a fixed spot in town.

November 28: the same handoff, from park to downtown

The Halloween schedule doesn't stand alone. The next big downtown day follows the same pattern.

The Chamber's Sierra Madre Winter Village page sets the Winter Festival & Shop Sierra Madre for Saturday, November 28, 2026, from noon to 5 p.m. Memorial Park hosts the Winter Festival, with the Holiday Artisan Marketplace, community booths, the Snow Sledding Hill and food vendors. From there the page invites people to shop and dine at businesses throughout downtown. The Community Christmas Tree Lighting follows at Kersting Court at 6 p.m. Once again the park holds the afternoon and downtown takes the evening. The Chamber says "More details coming soon."

The same day, Sierra Madre Playhouse at 87 W. Sierra Madre Blvd. opens Bob Baker's Nutcracker, a Bob Baker Marionette Theater adaptation. The Playhouse's Nutcracker page lists performances on November 28 and 29 and on December 5 and 6, 12 and 13, 15 through 20, 22 and 23, 26 and 27, and 29 and 30. Later in the season, the Playhouse hosts A Jet Set Christmas! with Matt Johnson & The New Jet Set on December 20 and 21 at 8 p.m.

So the town's two biggest public days this fall share a shape. Memorial Park holds the daytime crowd, downtown takes the evening, and different organizers run each leg. On October 31 the leg from park to storefronts starts at 2 p.m. On November 28 the evening gathering is the 6 p.m. tree lighting at Kersting Court.

If you're planning your Halloween route between Memorial Park and the boulevard, or you're wondering how life in Sierra Madre looks from one season to the next, we're always glad to talk about the town we serve. Reach out to the Chris Mardelli team anytime. Contact Us, and happy Halloween from our family to yours.