The Ultimate October San Diego Bucket List
October might just be San Diego’s best month. The air is crisp, sunsets turn gold, and the city’s fall energy brings together festivals, spooky fun, and cozy nightlife. Whether you’re a local or a visitor looking to make the most of the season, this October bucket list covers all the must-do experiences — from haunted adventures to elevated evenings at the city’s top cannabis lounges.
🎃 1. Visit the Whaley House in Old Town
Start spooky season right with a tour of one of the most haunted houses in America — the Whaley House. Join a candlelit ghost tour or take a self-guided stroll through Old Town to hear ghostly tales from San Diego’s early days.
🍂 2. Unwind at Sessions by the Bay – National City
After a long day (or night) of fall adventures, few places capture the relaxed spirit of San Diego like Sessions by the Bay. Located along the waterfront in National City, this elevated cannabis lounge and weed restaurant offers the perfect fall retreat.
Sip THC-infused mocktails, share gourmet edibles, or try curated flower blends while watching the bay lights shimmer. Whether you’re here to chill with friends or wind down solo, this cannabis bar and weed lounge blends local culture, art, and community in a stylish, welcoming atmosphere.
Sessions by the Bay isn’t just a weed bar — it’s a must-visit destination that belongs on every San Diegan’s October bucket list.
🎭 3. See a Show at The Old Globe
In the heart of Balboa Park, The Old Globe hosts world-class theatre all season long. This October, cozy up under the stars at the outdoor stage or catch a new production in the historic theatre — it’s pure San Diego magic.
🌇 4. Rooftop Season at The Nolen
Fall sunsets hit differently from above. The Nolen, one of downtown’s most beloved rooftops, offers panoramic views, seasonal cocktails, and fire pits perfect for sweater weather evenings.
🎶 5. Catch Live Music at The Casbah
If you’re into indie bands, rock shows, or local DJs, The Casbah in Midtown remains one of the city’s most authentic venues. It’s gritty, intimate, and full of energy — the kind of place where the night always surprises you.
☕ 6. Brunch at Morning Glory – Little Italy
No San Diego bucket list is complete without brunch, and Morning Glory nails it. Between the pink velvet booths, playful breakfast cocktails, and soufflé pancakes, it’s the perfect daytime indulgence before an evening out.
🕯️ 7. Explore the Art at Bread & Salt – Barrio Logan
Bread & Salt transforms old industrial space into an immersive art experience. Every visit brings something new — from local art exhibits and installations to live music and cultural pop-ups.
🌙 Final Hit: Fall in Love with October
From haunted tours and rooftops to creative weed lounges like Sessions by the Bay, San Diego in October is all about balance — a mix of thrill, chill, and pure California cool. Whether you’re exploring the city’s art, sipping seasonal cocktails, or watching the bay glow, make this October one to remember.
