October in Westchester and the Westside: Your 2026 Guide to Fall Events, In Order of Date

October is one of the best months to be in Westchester. The season brings weekly fall markets, the family-friendly Monster Dash costume run in Playa Vista, Halloween festivities and a pumpkin patch at the Sunday farmers market, and trick-or-treating plus a haunted house at Westchester Park, with a wealth of larger Halloween and harvest events a short drive away across Los Angeles. Here is a guide to the season's best community events, organized so you can plan your month from first to last.

There is a specific pleasure to fall on the Westside. The summer crowds thin, the weather stays mild, and the neighborhood leans into the season with the kind of genuine, family-oriented community events that make Westchester such a wonderful place to live. October in particular is packed with things to do, most of them free or inexpensive and nearly all of them centered on bringing neighbors together.

We are the Stephanie Younger Group, based right here in Westchester, and these local traditions are part of what we love about the neighborhoods we serve. Here is our guide to October, starting with the weekly markets you can enjoy all month, followed by the dated events in chronological order.

A note on dates: the weekly markets are reliable, but specific 2026 dates for the Halloween events below are calculated against this year's calendar and marked as expected. Halloween falls on a Saturday in 2026. Confirm details with each organizer before you go.

All Month: The Weekly Markets

These run every week throughout October and take on a distinctly seasonal, fall feel, with pumpkins, gourds, and autumn produce filling the stalls:

• Westchester Farmers' Market, Sundays — Historic Downtown Triangle, 6212 W. 87th Street (between Coffee Co. and Truxton's), Westchester. Over 50 farmers, growers, and artisans, with net proceeds supporting local community programs.
• Westchester Farmers' Market, Wednesdays — Westchester Park, Westchester.
• Playa Vista Farmers' Market, Saturdays, 9am to 2pm — RUNWAY Playa Vista, 12775 W. Millennium Drive. A community favorite since 2009, with organic produce, flowers, baked goods, live music, and a KidZone for families.
• Playa Vista Night Market, Wednesdays, 4 to 8pm — RUNWAY Playa Vista. An evening market with live music, fresh produce, artisanal vendors, and local food.

All Month, Select Nights: Halloween Attractions Nearby

These run on select nights across much of October rather than a single date, all within a drive of the Westside:

• Nights of the Jack — King Gillette Ranch, 26800 Mulholland Highway, Calabasas. A jack-o'-lantern trail on select nights, late September into early November.
• Carved at Descanso Gardens — Descanso Gardens, 1418 Descanso Drive, La Cañada Flintridge. A nighttime walk through thousands of carved and illuminated pumpkins, select nights October into early November.
• Oogie Boogie Bash — Disney California Adventure, Anaheim. Disney's popular Halloween party on select nights through October 31.

The Dated Events, In Order of Date

Here is the October calendar in chronological order, with locations:

Here is more detail on the local highlights:

Manhattan Beach Pumpkin Race Festival (mid-to-late October, expected) — A quirky, beloved South Bay tradition in downtown Manhattan Beach where decorated pumpkins race downhill, alongside a full day of family festivities. A short drive south of Westchester and a genuinely fun morning out.

Playa Vista Monster Dash (late October, expected) — A family-friendly costume run and walk along Bluff Creek Drive in Playa Vista. Grab your friends and your best costumes for a devilishly fun morning suitable for all ages. Check current registration details and the date as the event approaches.

Westchester Farmers' Market Halloween Festivities (Sunday, October 25, expected) — The last Sunday market before Halloween typically adds special festivities to the Historic Downtown Triangle: a pumpkin patch, extra community booths, Halloween story time for the kids, and seasonal treats. A low-key, family-friendly way to pick up a pumpkin and enjoy the community atmosphere.

Westchester Park Haunted House (Thursday to Saturday, October 29 to 31, expected) — For those who like their Halloween with a few more thrills, Westchester Park has hosted a haunted house across the Halloween weekend in past years, geared toward older kids and adults. Watch the LA Parks listings for Westchester to confirm this year's schedule and theme.

Westchester Park Halloween Celebration (Saturday, October 31) — The hub of neighborhood Halloween fun. The park's celebration typically features candy, a moon bounce, a costume contest, games, face painting, and more, an affordable, family-friendly way to celebrate the holiday close to home.

Día de los Muertos at Hollywood Forever (Saturday, October 31, expected) — One of the most vibrant Day of the Dead celebrations in the city, at Hollywood Forever Cemetery. Some years it is held the Saturday nearest November 2, so confirm the exact date before planning.

Why Fall Is Such a Good Time in Westchester

We write often about the practical advantages of Westchester, the central location, the market fundamentals, the community character. October is when that community character is on full display. The pumpkins at the Sunday market, the costume run through Playa Vista, the kids trick-or-treating at Westchester Park, the neighbors running into each other at the fall markets, this is the texture of daily life that makes people fall in love with the neighborhood and stay for decades.

For anyone considering Westchester as a place to live, October is a wonderful time to experience it firsthand. And for those of us who already call it home, the fall calendar is a reminder of exactly why we do.

The Stephanie Younger Group is based in Westchester at 7296 W. Manchester Avenue. Whether you want to talk real estate or just chat about the neighborhood, reach out at 310.499.2020 or online. We hope to see you around the neighborhood this fall.

Event dates and details are subject to change year to year. Dates marked "expected" are calculated against the 2026 calendar and should be confirmed with each event's organizer before attending.

Frequently Asked Questions

Q: What October events happen in Westchester, Los Angeles?

Westchester offers several family-friendly October traditions. The Westchester Farmers' Market typically holds special Halloween festivities on the last Sunday before Halloween (expected October 25, 2026), including a pumpkin patch, community booths, Halloween story time, and treats, in the Historic Downtown Triangle at 6212 W. 87th Street. Westchester Park usually hosts a Halloween celebration on October 31 with candy, a moon bounce, a costume contest, games, and face painting, and has featured a haunted house across the Halloween weekend in past years. The weekly Sunday and Wednesday markets also take on a fall feel throughout the month.

Q: When is the Playa Vista Monster Dash in 2026?

The Monster Dash is an annual family-friendly costume run and walk held along Bluff Creek Drive in Playa Vista, typically in late October. The specific 2026 date had not been published at the time of writing, so confirm current registration details and the date with the organizer as the event approaches. Participants are encouraged to wear their best Halloween costumes for a fun, active morning suitable for all ages.

Q: Is there a pumpkin patch in Westchester?

Yes. The Westchester Farmers' Market typically sets up a pumpkin patch as part of its late-October Halloween festivities in the Historic Downtown Triangle at 6212 W. 87th Street, expected on Sunday, October 25, 2026. It is a convenient, community-oriented spot to pick up a pumpkin while browsing fall produce. For larger pumpkin patches and harvest festivals, options a short drive away include Underwood Family Farms in Moorpark.

Q: What Halloween events are good for families on the Westside?

Westchester Park's Halloween celebration on October 31, with candy, a moon bounce, costume contest, games, and face painting, is a great low-cost family option. The Playa Vista Monster Dash costume run in late October is another family favorite, and the Westchester Farmers' Market Halloween festivities (expected October 25) suit younger children. A short drive away, the Manhattan Beach Pumpkin Race Festival, and the nighttime pumpkin walks at Descanso Gardens (Carved) and King Gillette Ranch (Nights of the Jack), are all excellent family outings.

Q: When is the Westchester Farmers' Market and what happens there in the fall?

The Westchester Farmers' Market runs every Sunday in the Historic Downtown Triangle at 6212 W. 87th Street and every Wednesday at Westchester Park, featuring over 50 farmers, ranchers, growers, and artisans. In October, the market fills with fall produce, pumpkins, and gourds, and the last Sunday market before Halloween (expected October 25, 2026) typically adds Halloween festivities including a pumpkin patch, community booths, and kids story time. Market proceeds support local community programs.

Q: What bigger LA fall events are near the Westside in October?

Within a reasonable drive, October highlights include the Manhattan Beach Pumpkin Race Festival in the South Bay (mid-to-late October), Nights of the Jack at King Gillette Ranch in Calabasas and Carved at Descanso Gardens in La Cañada Flintridge for nighttime pumpkin displays, Día de los Muertos at Hollywood Forever Cemetery, and the Oogie Boogie Bash at Disney California Adventure in Anaheim. The central Westside location makes all of these accessible for a fall day out.