The Town Named After Pumpkins Just Split Its Pumpkin Season in Two

Ask a longtime Calabasas resident where the city's name comes from and most people reach for the same story: a wagon loaded with pumpkins overturned somewhere along the old trail through these hills, the pumpkins scattered, and the name stuck. The City of Calabasas still tells its own version of that legend, crediting explorer Juan Bautista de Anza's travels through the area for the spill that eventually gave the city its calabaza, the Spanish word for pumpkin or gourd.

For most of the year that history sits quietly in the background. Not this fall. Starting in late September, Calabasas is effectively running two separate pumpkin operations at the same time, a few miles apart, and they have almost nothing in common except the squash.

One Sunday, one park, and a mascot named Punky

The city's own answer to its history is the Calabasas Pumpkin Festival, returning to Juan Bautista de Anza Park on Sunday, October 18, from 10 a.m. to 5 p.m. This is the small-scale version of the tradition: a single afternoon, a single park, more than 75 marketplace vendors, food trucks, a pumpkin patch, live music, and photo opportunities with the festival's mascot, Punky, alongside other seasonal characters. Advance tickets run $15, day-of admission is $20, and children under two get in free.

The logistics are built for a walk-in family afternoon rather than a planned evening. Free parking is available in designated business lots along Lost Hills Road and Agoura Road, with a complimentary shuttle running to the main gate, and residents can also request a ride to the festival gate through the city's own on-call Calabasas Flyer shuttle rather than hunting for street parking.

A monthlong, after-dark version up the highway

Up on Mulholland Highway, King Gillette Ranch is hosting the other half of Calabasas's pumpkin season: Night of the Jack, back for its ninth year and running select nights from September 25 through November 1. This is not a city event. It is a privately produced, ticketed show built around a reimagined one-mile walking trail lined with thousands of hand-carved, illuminated jack-o'-lanterns, timed entry slots, and a 21-and-over Spookeasy bar. Recent coverage from LAmag puts its typical season turnout above 100,000 visitors across the full run, a scale the single-Sunday city festival was never built to match.

The headline change for 2026 is Jack's Carnival, a new addition bringing more than ten rides and attractions to the grounds for the first time, layered on top of the existing walking trail. Pricing reflects that expansion, and it is worth knowing the breakdown before assuming this is a single flat-rate night out:

• Trail admission starts in the mid-$20s on weeknights and climbs into the $60s and beyond for peak weekend and near-Halloween dates, according to Travelzoo's current listing.
• A flexible "Anytime" ticket, for guests who do not want to commit to a specific date, runs $83.
• Parking is sold separately as a $15.98 pass, purchased in advance, with none available for sale at the lot itself.
• An unlimited carnival ride wristband adds another $35 on top of trail admission.

Gates open at 5:30 p.m., the trail itself runs on timed entry slots between 6 and roughly 8:30 p.m., and the whole property closes by 10, with the parking lot cutting off at 9 sharp. A family of four planning to walk the trail, ride the carnival, and grab dinner from one of the food trucks is looking at a night that adds up in pieces, not a single admission price.

The half nobody puts on the ticket page

Here is the detail that neither event's marketing mentions in the same sentence: King Gillette Ranch is a public park, and it stays open for daytime walking, decorations included, until 4 p.m., even during the weeks Night of the Jack is running its ticketed evening show on the same grounds. Visitors who have made the trip have documented exactly this online, a free daytime pass through the same Santa Monica Mountains setting, including the Ridge Trail and the ranch's visitor center, hours before the paid trail opens for the night.

That changes the math for anyone weighing whether Night of the Jack is worth the price. A Calabasas household does not have to choose between the free version and the ticketed version on a single visit. A Saturday afternoon hike through King Gillette Ranch, taking in the same grounds and much of the same seasonal decor at no cost, is a completely separate outing from a Friday night walk through the lit trail after dark. They are stacked on the same property at different hours, not competing for the same trip.

What doesn't pause for either one

None of this touches the market that keeps running underneath both events. The Old Town Calabasas Farmers Market, on Calabasas Road just west of El Canon Avenue across from the Sagebrush Cantina, holds its Saturday morning slot from 8 a.m. to 1 p.m. year round, festival season or not. It is the kind of fixture that never needs a press release, which is exactly why it belongs in this picture. The pumpkin season around it gets louder and more expensive every year, but the Saturday market a few blocks from Old Town keeps the same three-hour window regardless of what is happening at the park or up the highway that weekend.

That is really the story of this fall in Calabasas. A city whose entire name traces back to a joke about a spilled wagonload of squash is now home to two separate pumpkin economies running at the same time, one civic and single-day, one commercial and month-long, one nearly free and one billed in tiers. They sit close enough together, in both geography and calendar, that a single household could reasonably take in all three versions this season, the city festival, the free daytime ranch walk, and the paid night trail, without double-booking a single weekend.

Whether you have lived off Mulholland for twenty years or moved into Old Town last spring, that overlap is worth planning around before the better Night of the Jack dates sell out. It is also a small but useful read on what living near this stretch of Calabasas actually looks like across the calendar, not just in October. If you are curious what a specific street or neighborhood here feels like in every season, not only pumpkin season, Robert Edie is worth a call.