Things To Do in and Around Calabasas: Local Events Guide (May 2026)

Looking for the best things to do in Calabasas right now? Whether you're a longtime resident, a new neighbor, or considering a move to one of the San Fernando Valley's most desirable communities, this hyper-local events guide covers everything happening in and around Calabasas from late April through the end of May 2026 — including farmers markets, wine tastings, live music nights, folk festivals, outdoor concerts, and community staples you won't want to miss.

Bookmark this page. It's updated regularly so you always have a go-to answer when you ask: "What's happening in Calabasas this weekend?"

Quick-Answer Event Calendar: Calabasas Area, April 26 – May 31, 2026

Every Saturday: Old Town Calabasas Farmers Market

The anchor of Calabasas weekend life.

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When:

• Every Saturday, 8:00 AM – 1:00 PM, year-round >

Where:

• 23504 Calabasas Rd, Calabasas, CA 91302 >

Admission:

• Free >

Upcoming dates in May:

• May 2, May 9, May 16, May 23, May 30

Tucked into the heart of historic Old Town Calabasas, this certified farmers market is where the community actually comes together every weekend. Shop seasonal produce, farm-fresh eggs, artisan bread, honey, flowers, handmade goods, prepared foods, and specialty vendors from across the region.

Pro tip: Arrive early for the best selection, then stay for brunch at nearby Old Town spots before exploring the boutiques along Calabasas Road.

Thursday, May 7: 27th Annual Calabasas Wine Tasting & Silent Auction

The community event of the season — and a Calabasas Chamber tradition.

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When:

• Thursday, May 7, 2026 | 5:30 PM – 8:00 PM PDT >

Where:

• Calabasas Civic Center Plaza, 100 Civic Center Way, Calabasas, CA >

Tickets:

• $70 advance (through May 6) | $85 at the door | $275 for a 5-pack >

Age:

• 21+ | Valid ID required

Now in its 27th year, this is the signature annual event hosted by the Calabasas Chamber of Commerce. Expect fine wine from local and regional producers, food from beloved local eateries, a vendor boutique, live music, and a silent auction featuring premium items — all set at the beautifully curated outdoor Civic Center Plaza.

Whether you're a longtime Calabasas resident or recently moved into the area, this is one of the best networking and social evenings of the year. Don't miss it.

Sunday, May 17: Topanga Banjo Fiddle Contest & Folk Festival

Calabasas's biggest outdoor festival of the spring — 65 years strong.

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When:

• Sunday, May 17, 2026 | 9:00 AM – 6:00 PM (Featured performers from 12:00 PM) >

Where:

• King Gillette Ranch, 26800 Mulholland Highway, Calabasas, CA 91302 >

Tickets:

• Available at my805tix.com >

Compete deadline:

• May 10, 2026 ([email protected])

Since 1961, the Topanga Banjo Fiddle Contest & Folk Festival has brought Southern California's best old-time, bluegrass, folk, and dance traditions to life in the hills of Calabasas. The 2026 edition spans five stages across the stunning grounds of King Gillette Ranch — one of the most scenic outdoor venues in greater Los Angeles.

2026 Lineup Highlights

Main Stage: Sweet Megg with Water Tower · Jordan Tice · Jake Blount · Foghorn Stringband · Cowboy Poetry by Jessica Schley & Zane York

Tiny Porch Stage: The Prairie Moons · Whole Hog (2025 Band Competition Winners) · Banjo Kitty · The Guesthouse

Dance Stage: Flatfoot dance workshop · Step dance competition · Square dance · English country dance · Contra dance · Waltz workshop

Family Stage: Beginning fiddle classes · Our First Rodeo · Peach & Spoon · Sweet Potato Music · Happy Campers · Santa Monica Ballet Folklorico · Children's craft and instrument petting zoo

Food: Food trucks on-site, or bring your own picnic and cooler. Over $6,500 in cash and gift prizes for competitors.

This is a full family day that perfectly captures why people love living in Calabasas.

Sunday, May 10: Tiny Porch Concerts Season Opener — Two Runner

Intimate outdoor music in the canyon. A hidden local gem.

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When:

• Sunday, May 10, 2026 | 5:00 PM >

Where:

• Peter Strauss Ranch, Agoura Hills, CA (approx. 10 minutes from Calabasas) >

Tickets:

• my805tix.com | VIP season passes also available

The Tiny Porch Concerts series kicks off its 2026 outdoor season at the iconic Peter Strauss Ranch in Agoura Hills. Two Runner headlines this intimate, sunset-hour concert surrounded by old oaks and the sounds of the Santa Monica Mountains. Future shows run June 7, July 19, and August 16 — but the May 10 opener is the one to catch first. Low-key, high-quality, quintessentially Calabasas-area living.

Live Music Every Weekend: The Canyon – Agoura Hills

Your neighborhood concert venue. Dinner + a show, 10 minutes from home.

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Where:

• 28912 Roadside Drive, Agoura Hills, CA 91301 >

Tickets & Info:

• wheremusicmeetsthesoul.com >

Phone:

• 888-645-5006 >

Vibe:

• Full dinner service, cocktails, reserved seating — no need to drive into Hollywood

The Canyon – Agoura Hills is the 101 corridor's most active live music venue, and their May 2026 calendar is stacked. Every show is an easy dinner-and-concert night for Calabasas residents.

Full May 2026 Concert Calendar at The Canyon – Agoura Hills

Saturday, May 2 | 6:00 PM
Prescott Niles' The Knack + Opening Sets by Ready or Not and Guilty Pleasures

Thursday, May 7 | 6:00 PM
Black Sabbath Tribute by Sabbath Resurrected & Motörhead Tribute by Murdërone + Opening Set by Mancini Rocks

Saturday, May 9 | 9:00 PM
Oingo Boingo Former Members

Sunday, May 10 | 5:00 PM — Mother's Day
Fantastic Diamond: Neil Diamond Tribute + Opening Set by Darren Block
Perfect Mother's Day evening out

Tuesday, May 12 | 6:00 PM
An Evening with Brandy Clark + Opening Set by Olivia Wolf

Thursday, May 14 | 7:30 PM
Forever Rod: Rod Stewart Tribute

Saturday, May 16 | 6:00 PM
Wild Child – A Live Recreation of a 1960s Doors Concert + Opening Sets by Anna May and Deepest Purple

Sunday, May 17 | 6:00 PM
The Walt Johnson Frank Sinatra Tribute featuring Michael Falcone

Thursday, May 21 | 8:00 PM
Babes Against the Machine (Rage Against the Machine Tribute) | Tickets from $57

Friday, May 22 | 9:00