Halloween is creeping closer, and the East Bay is buzzing with a brew of harvest flavors, haunted legends, and festive gatherings. From ghostly walks in historic towns to craft fairs bursting with autumn treats, this week is packed with cozy chills and spirited thrills. Whether you’re hunting for pumpkin‑spiced fun, dazzling Diwali lights, or a witchy wine walk, there’s magic in the air — and the East Bay is the perfect place to celebrate it all.

Spotlight
🧙‍♀️ Witching Wine Walk – Benicia
📅 Sat, Oct 18 | 1–5pm
📍 Downtown Benicia (First Street)

Join us on Saturday, October 18th | 1–5 PM for an enchanting afternoon of wine tasting, shopping, and community fun along the Benicia Strip! ✨

Hundreds of costumed “witches” will descend upon First Street in downtown Benicia to sip and stroll at this haunted wine tasting adventure. Your ticket includes up to 15 wine tastings and a souvenir glass, with 25+ local businesses offering pours and tasty bites along the route. Grab your ghoul-friends, don a witch’s hat, and get ready for a spellbinding afternoon of sips, snacks, and spooky fun in this annual Halloween-themed wine walk. Costumes are encouraged — add a little Halloween spirit to your stroll and make the day even more festive!

Twin Oaks will be part of the celebration, so we’re inviting everyone to come catch us while enjoying the festivities.

🪅 Sazón Latin Food Fest – Alameda
📅 Sat, Oct 18 | 11am–6pm
📍 Faction Brewing, Alameda
💵 Free (registration required)

Take your taste buds on a trip across Latin America at this vibrant outdoor food festival by the bay. Sazón Latin Food Fest brings together a curated lineup of Latin American food vendors representing the best flavors from the Caribbean, Central and South America. There will be great music, refreshing drinks, and a family-friendly atmosphere – so come hungry and bring friends, because you’ll want to try a bit of everything (including irresistible desserts!). Admission is free with an RSVP (space is limited), so grab your ticket and get ready for a fiesta of food, music, and culture on Alameda’s waterfront.

🏞️ Sunol Heritage Festival – Sunol
📅 Sat, Oct 18 | 11am–3pm
📍 Sunol Wilderness Regional Preserve, Sunol
💵 Free ($5 parking)

Celebrate the diverse “heritage of the wilderness” at this fun, all-ages festival that brings the old West to life in Sunol’s beautiful regional park. History and nature join forces with live folk music by the Polka Cowboys, Ohlone storytelling and acorn treats, folklórico dance, and dozens of hands-on activities throughout the day. Kids and adults alike can try traditional crafts – make a branded bandana, fashion a mini tule boat, string a pine-nut bead bracelet – or play old-timey games like grain sack races and even practice lassoing a (wooden) cow. Pack a picnic and enjoy a day in the park celebrating local indigenous and ranching heritage; it’s free family fun in the fresh air (just $5 for parking).

🐾 Pawstoberfest – Brentwood
📅 Sun, Oct 19 | 11am–6pm
📍 City Park, Brentwood
💵 Free

Calling all dog lovers – this “pawsome” festival is essentially a canine-themed Oktoberfest and fall fair rolled into one. Pawstoberfest will take over Brentwood’s City Park with a beer & wine garden pouring local brews, a fleet of food trucks, 30+ pet-friendly vendors and artisans, and even a doggy costume contest/parade with awesome prizes for the best-dressed pups. You can meet adoptable dogs at the puppy corner, get your furry friend microchipped or vaccinated on-site, watch cool K9 demonstrations, and let the kids enjoy a dedicated play zone with lawn games. With live music keeping the party going and a silent auction raising funds for rescue efforts, it’s a tail-waggin’ good time – plus free admission for all, with registered attendees scoring a complimentary beer mug or wine glass at check-in (while supplies last).

🪔 Oakland Diwali Festival – Oakland
📅 Fri, Oct 24 | 6–10pm
📍 BLOC15, Oakland
💵 Free (includes food & entertainment)

Oakland’s own Diwali celebration lights up the night with a free, all-ages festival of South Asian culture and community. Oakland Diwali brings together hundreds of people from all backgrounds to enjoy dynamic Bollywood and folk dance performances, live music, and delicious South Asian cuisine – all in honor of the Festival of Lights. This year’s party promises to be bigger and brighter than ever, mixing authentic Indian traditions with an Oakland twist. Get ready to dance your heart out, savor flavorful bites, and soak up the joyful, inclusive vibes of this not-to-miss cultural celebration.

🛍️ Harvest Festival Art & Craft Show – Pleasanton
📅 Fri–Sun, Oct 24–26 | 10am–5pm
📍 Alameda County Fairgrounds, Pleasanton
💵 $4–9 (kids 12 & under free)

Shop til you drop at one of the Bay Area’s biggest annual arts & crafts extravaganzas. The Harvest Festival returns to Pleasanton, transforming the fairgrounds into a huge marketplace of original, handmade treasures from hundreds of talented artists and makers. Discover an array of one-of-a-kind goods – from beautiful wall art, sculptures and jewelry to hand-turned woodwork, ceramics, specialty foods, holiday décor and more – there’s something for everyone at this celebration of creativity and craftsmanship. Don’t miss this chance to support local artisans and find unique gifts (or treat yourself) while experiencing the magic of the Harvest Festival’s lively atmosphere.

📍401 1st St, Benicia, CA 94510

Step through the doors of Union Hotel Restaurant & Bar on First Street, and you’re stepping into a slice of Benicia’s haunted past — where the clink of silverware mingles with whispers from another era. Nestled inside this 1852 landmark, diners have claimed to glimpse a spectral figure gazing from the upstairs windows, or hear lonely footsteps echoing through silent hallways.

Yet the ghost stories don’t stop the warmth: by candlelight, you’ll be treated to bold seasonal flavors and attentive service in a setting that balances historic elegance with fall’s cozy chill. Visit the Union at dusk, settle in with a glass of wine — and if you happen to catch a flicker at the edge of your vision, just raise your glass: you’re in good (and spirited) company.

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As the nights grow longer and the pumpkins glow brighter, we hope these East Bay events, legends, and local flavors keep your October full of festive spirit. Until next week, may your harvest be bountiful, your ghost stories thrilling, and your weekends filled with just the right mix of cozy chills and community cheer.

Stay local & stay inspired,

Ryan DeAmaral

Co-Writer, Twin Oaks Insider

[email protected]