Start on Santana Row, Where Halloween Runs for a Month
The Row is where the season announces itself. On a Saturday afternoon in October the street between the shops fills with tents and folding tables, the smell of kettle corn and coffee drifting between them, and by the time the light drops behind the trees at Park Valencia the whole block is loud with live music and dogs on leashes. This is Santana Row, 377 Santana Row, San Jose — a shopping and dining district that treats autumn as a full calendar rather than a single night. Everything below happens on and around these blocks, and most of it costs nothing to walk into.
Shop the Makers Market and the Cultural Pop-Up
The seasonal markets are the easiest way to spend a slow Saturday. Plan around these recurring and dated gatherings:
- Makers Market's Local Artist Street Fair — the second Saturday of the month, 11am–6pm, running October 10 in 2026. More than 60 local makers set up with jewelry, ceramics, woodwork, apparel, candles, honey and apothecary goods. It's a sip-and-stroll format with live music, free admission, and it's friendly to kids and dogs.
- Día de Los Muertos cultural pop-up market — November 1, 12–5pm, part of the Day of the Dead celebration. Crafts and vendors alongside the altars.
- Community ofrendas — also November 1, on view from the 10:30am brunch window at Zazil onward. These are the altars local families and groups build for the holiday; walk them slowly.
Watch Giant Pumpkins Get Sculpted at Park Valencia
Farmer Mike brings the knives and the scale of the thing is the point: live giant-pumpkin carving at Park Valencia, billed as "Pumpkin Picasso." Two windows in 2026 — Saturday October 24, 10am–1pm, and Sunday October 25, 12–2pm. Come early if you want a clear sightline; the crowd thickens as the sculpting gets detailed. Park Valencia is the pumpkin-carving venue, and it's worth knowing the spot by name before you go.
Bring the Kids to Trick-or-Treat The Row
The anchor Halloween event is the Trick-or-Treat The Row Halloween Family Festival on Tuesday, October 27, 10am–12pm. It's free and open to the public, costumes encouraged, and it spreads along the Row with live music, pumpkin decorating, stilt-walkers and balloons. Trick-or-treat stops are announced closer to the date. If you're travelling with children, build your day around this window and let the rest of the afternoon drift.
Catch Short Films, Supercars and Mariachi
The Row's October and November programme reaches well past pumpkins:
- 18th Annual San Jose International Short Film Festival — October 22–25 at the Ciné Arts Theater, with more than 100 short films from around the world and filmmaker Q&As. Schedule and tickets at sjsff.com.
- Cars & Croissants on The Row — Sunday, October 18, 9am–12pm. An exotic and supercar gathering, free to attend; display space for your own vehicle can be reserved.
- Día de Los Muertos Celebration — Sunday, November 1, a free community day with face painting, Catrina and Catrín meet-and-greets, mariachi, crafts and the pop-up market. The schedule stacks neatly: brunch and ofrendas at Zazil from 10:30am; market 12–5pm; Catrina photo ops at Oak Tree Lounge and face painting at Santana Row Park 12–3pm; mariachi and dance at Santana Row Park 1–3pm; mariachi and face painting at El Jardín Tequila Bar 3–4:30pm; mariachi at Zazil 4:30–6pm.
Eat, Stay and Time Your Visit
Food and drink are built into the calendar rather than bolted on. Zazil hosts the Día de Los Muertos brunch from 10:30am and closes the day with mariachi from 4:30–6pm; El Jardín Tequila Bar carries the mid-afternoon mariachi and face-painting shift; Oak Tree Lounge is the Catrina photo-op setting. For an overnight, Hotel Valencia Santana Row puts you inside the district, which matters on festival days when parking and foot traffic peak. If you want one date, October 27 gives you the family festival; if you want the fullest weekend, aim for October 24–25 for the pumpkin carving with the short film festival running alongside; if you'd rather skip Halloween entirely and go straight to the altars, book November 1. For anything time-sensitive, the district's events line is 408.551.4611.
Block the dates now — the second Saturday of October for the makers, the 24th and 25th for the pumpkins, the 27th for the costumes, and November 1 for the mariachi and the ofrendas — and the rest of the trip arranges itself around a single stretch of San Jose street.