Unique & Unusual Halloween Events Near Cupertino 2026

13 unique & unusual Halloween events near Cupertino

Illustration of a haunted mansion with glowing windows and tiny ghosts at dusk, with jack-o'-lanterns and bats nearby (Winchester Mystery House Tours)

Winchester Mystery House Tours

San Jose $$

Explore a 160-room mansion with baffling architecture and a mysterious history.

Illustration of clay figures walking past striped market stalls and pumpkins on a paved square with orange autumn trees (Safeway World Championship Pumpkin Weigh-Off)

Safeway World Championship Pumpkin Weigh-Off

Mon, Oct 12

Half Moon Bay 24 mi Free

Growers compete for prizes with massive, Volkswagen-sized pumpkins.

Illustration of a Halloween town at twilight with glowing houses, jack o lanterns, ghosts, and a witch flying past the moon (Pleasanton Rotary Halloween Spirit Run)

Pleasanton Rotary Halloween Spirit Run

Sun, Oct 25

Pleasanton 25 mi $$$

Costume-friendly 5K, 10K, and kids races through Downtown Pleasanton

Illustration of white ghosts floating over houses with glowing windows and pumpkins, with a witch flying past a full moon (Thrill the World Zombie Crawl)

Thrill the World Zombie Crawl

Sat, Oct 24

Campbell 5 mi Free

Costumed zombies perform Michael Jackson's Thriller dance across downtown restaurant stops.

Illustration of small clay figures in costumes and ghosts painting pumpkins at a long table under bunting at dusk (Sip and Paint: Colors of Fall at 25 West Gallery)

Sip and Paint: Colors of Fall at 25 West Gallery

Sat, Sep 19

Mountain View 5 mi $

Relaxed watercolor painting session exploring autumn tones with all materials provided.

Illustration of a Halloween town at dusk with glowing houses, pumpkins, floating ghosts and a witch flying past a full moon (Slash and Sip: Adult Pumpkin Carving at San Pedro Square Market)

Slash and Sip: Adult Pumpkin Carving at San Pedro Square Market

Fri, Oct 23

San Jose 8 mi $$

Carve and decorate pumpkins outdoors under the stars in downtown.

Illustration of a Halloween craft scene with clay kids, a friendly ghost, bats and glowing pumpkins under party bunting (Spooky Papier-Mâché Mask Workshop)

Spooky Papier-Mâché Mask Workshop

Oct 24 – Oct 25

Los Gatos 8 mi $$

Two-day mask making workshop led by artist Leyla Carleo.

Illustration of glowing jack-o'-lanterns, candles and scattered seeds on a wooden table under string lights at dusk (Pumpkin Succulent Workshop at Hayes Mansion)

Pumpkin Succulent Workshop at Hayes Mansion

Sat, Oct 17

San Jose 12 mi $$

Craft a living centerpiece using fresh pumpkins, succulents, and seasonal accents.

Illustration of a Halloween town at night with glowing windows, pumpkins, floating ghosts and a witch flying past a full moon (Campbell Oktoberfest Fun Run)

Campbell Oktoberfest Fun Run

Sat, Oct 17

Campbell 6 mi $$$

Scenic 10K, 5K, and Kids' Dash with optional lederhosen.

Illustration of friendly ghosts on small town rooftops with pumpkins and glowing windows as two witches fly past a full moon (What Spooky Child Is This?)

What Spooky Child Is This?

Sun, Oct 4

Livermore 29 mi $$

Blacklight family painting session using glow-in-the-dark neon paints under UV lights.

Illustration of a town street at twilight with glowing windows, pumpkins, floating ghosts and a witch on a broom by the moon (Rustic Pumpkin Trio on Canvas)

Rustic Pumpkin Trio on Canvas

Sun, Oct 4

Livermore 29 mi $$$

Step-by-step guided autumn canvas painting session with optional candle making.

Illustration of a Halloween town at night with glowing windows, pumpkins, floating ghosts and a witch flying past a full moon (Sama-Sama Fest at Union Landing)

Sama-Sama Fest at Union Landing

Union City 19 mi Free

City's first Filipino American History Month celebration

Illustration of a Halloween town at night with glowing windows, pumpkins, floating ghosts and a witch flying past a full moon (31 Skulls Showcase & Auction)

31 Skulls Showcase & Auction

San José 8 mi $$

Live auction of 186 artist-donated skulls

Unique & Unusual Halloween Events this weekend Oct 16–18

Sat17Oct Pumpkin Succulent Workshop at Hayes MansionSan Jose

Sat17Oct Campbell Oktoberfest Fun RunCampbell

Other Halloween categories near Cupertino

Illustration of small costumed children and a witch on a sunny autumn lawn with pumpkins, hay bales and orange trees

CupertinoFamily-Friendly Fall Activities50 family events

Illustration of a Halloween gathering at dusk with a smiling ghost, costumed figures, glowing jack-o'-lanterns and lights

CupertinoHalloween Food, Drink, and Parties27 parties & tastings

Illustration of a small cottage with glowing windows, ghosts, jack o'lanterns and black cats under a full moon at dusk

CupertinoHaunted Experiences11 haunted attractions

Illustration of a pumpkin character and a ghost performing on a lit stage with red curtains before a crowd at night

CupertinoHalloween Movies, Theater, and Entertainment6 shows & screenings

About Unique & Unusual Halloween Events near Cupertino

For a grand Halloween experience, consider the elaborate Winchester Mystery House in San Jose. If you prefer a more local, community feel and a free activity, the Safeway World Championship Pumpkin Weigh-Off in Half Moon Bay might be your preference.

Beyond these, a wealth of Halloween events await. Browse the cards below to find everything from family-friendly workshops to adult-oriented painting sessions, each located in Cupertino or nearby towns like San Jose and Mountain View.

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Halloween Events Near Me

13 unique & unusual Halloween events near Cupertino

Unique & Unusual Halloween Events this weekend Oct 16–18

Other Halloween categories near Cupertino

About Unique & Unusual Halloween Events near Cupertino

Find Unique & Unusual Halloween Events on Our Map!