Cheers to 20 years!
The annual Montana Avenue Art Walk will celebrate its milestone anniversary on October 3 with the debut of food trucks and open containers of alcohol.
The “Entertainment Zone” that debuted on Third Street Promenade in 2025 will be expanded –– for one day only –– to include most of Montana Avenue between 7th and 17th Streets.
“The event keeps growing,” says Michelle Kelly, president of the Montana Avenue Merchants Association. “This is also the first year that we are expanding the footprint. We are going to have multiple activations throughout these 10 blocks.”
The event, which kicks off at 11 a.m., will include complimentary fitness classes, live music, an art zone for kids, pet adoptions and creations from over 150 artists.
One initial announcement projected up to 10,000 guests could attend. But Kelly tells the Sun her expectations are more grounded: “Every year we just hope we have more people than the year before.”
Humble beginnings
The Art Walk began in 2006 as a way to drum up business for shop owners in one of Southern California’s most upscale retail districts. In its earliest days, local artists literally set up inside participating storefronts. As crowds grew year over year, the festival moved onto the pavement, eventually taking over eight blocks.
This year’s expansion down to 7th Street marks the event’s largest physical footprint to date — and its first year as an official City of Santa Monica “Signature Event.”
In the zone
While open-container rules generated fierce debate when first proposed for the Promenade, organizers on Montana are emphasizing a strictly controlled execution. Restaurants serving “to-go” drinks were required to complete a special training last week, and possession of alcohol will be restricted strictly to the vehicle-restricted street perimeter between 11:00 a.m. and 6:00 p.m.
If the pilot is successful, it’s possible that drinks may flow more freely future Montana Avenue festivals.
“As a board, we talked about only being open to having the Entertainment Zone for events where the street is closed to vehicle traffic,” Kelly said. “We would not entertain it for any other type of event. It’s expensive to close the street and requires extra security and fees.”
To complement the drinks, the association is also bringing in food trucks for the first time. They will be stationed strategically between 7th and 9th Streets—an area anchored by local schools and banks with fewer brick-and-mortar eateries—to draw foot traffic down the newly added blocks without undercutting established local restaurants.
Behind the scenes
Bringing on outside event producers Venice Blvd Productions has helped attract high-profile sponsors like MINI, Gatorade, and UCLA Health. But despite the added corporate muscle, Kelly notes that putting on a 10-block street fair in Santa Monica is a massive financial balancing act involving off-duty police, traffic pattern rerouting, street barricades, and offsetting lost parking meter revenue.
“It is very expensive to put on an event in the city,” she says “We’ll be happy if we don’t lose money and break even because it is a promotional event.”
The Art Walk traditionally takes place on the last Saturday of September. This year, it was moved back a week to not conflict with the since-canceled Ocean Way Festival at Santa Monica Beach.
And while open containers, food trucks, and classic car displays give this year’s Route 66 Centennial edition a distinctly broader street-party feel, Kelly insists the neighborhood institution hasn’t forgotten its roots.
“The event could continue to evolve, but it remains deeply grounded in art,” Kelly said. “The Art Walk is the big focus of our year.”
Event Details
- What: 20th Annual Montana Avenue Art Walk (Route 66 Centennial Celebration)
- When: Saturday, October 3, 2026 | 11:00 a.m. – 6:00 p.m.
- Where: Montana Avenue (Closed to vehicles from 7th to 17th Streets; north-south traffic remains open at Lincoln, 11th, and 14th)
- Admission: Free
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