Fall Events and Activities in San Carlos and the Mid-Peninsula
Fall in San Carlos and the Mid-Peninsula brings crisp mornings, beautiful weather, and some of the year's best community events.
This guide highlights the must-attend fall events and seasonal activities that make San Carlos, Belmont, Redwood City, and surrounding areas such great places to live! (Looking to join the community? Contact our top San Carlos real estate agents.)
The Mid-Peninsula' fall event calendar offers something for everyone, from traditional cultural celebrations to community gatherings that bring neighbors together. Here's a guide to some of the season's best events.
Oktoberfest - Downtown Redwood City
September 19-28, 2025 | Courthouse Square
Authentic German celebration with Munich-inspired tent, traditional music, stein-holding challenges, and Bavarian cuisine. Tickets $10-$35 include commemorative stein and drink. VIP table seating available for $250 on weekends.
September 27, 2025, 7:00 AM | Twin Pines Park
Annual community event featuring 5K, 10K, 1-mile kids run, and 1-mile Fido run. Perfect showcase of the active lifestyle that makes Belmont appealing.
October 11-12, 2025, 10:00 AM - 6:00 PM | San Carlos Avenue at Laurel Street
Peninsula's premier fall festival featuring 225+ artists, fine wines, microbrews, and Family Fun Zone. Free shuttles and parking available. Easily accessible via Caltrain, making San Carlos the place to be.
Half Moon Bay Art & Pumpkin Festival
October 18-19, 2025 | Half Moon Bay (Pumpkin Weigh-Off October 13)
53rd annual festival featuring world championship pumpkin weigh-off, pie eating contests, live music, and costume contests. The scenic coastal drive highlights why Peninsula living is so desirable.
October 19, 2025 | Belmont Library
Free Festival of Lights celebration featuring music, dance, poetry, and traditional activities curated by the City of Belmont.
October 29, 2025 | Twin Pines Park
Free spooktacular event with trunk-or-treat, haunted buildings, live music, and food trucks. Costumes encouraged for this family-friendly Halloween celebration.
Dia de los Muertos Celebration
November 3, 2025 | Various Redwood City venues
Traditional celebration with altar competitions, live performances, sugar skull workshops, Catrina face painting, and ceremonial procession throughout Redwood City.
Patchwork Show Craft & Maker Fest
November 9, 2025, 11:00 AM - 5:00 PM | Courthouse Square, Redwood City
FREE festival featuring local makers, handcrafted goods, live music, and DIY activities. Pet-friendly event supporting small businesses in the community.
These events bring together the local spirit that make our Mid-Peninsula communities throughout the Mid-Peninsula so attractive to residents and visitors alike.
Beyond the scheduled events, the Mid-Peninsula offers plenty of seasonal activities that make fall special for families throughout our communities. From pumpkin picking to scenic foliage viewing, here's your guide to autumn's best family adventures.
Pumpkin Patches in Half Moon Bay
October Season | Various Half Moon Bay locations
Top Peninsula pumpkin destination featuring Lemos Farm, The Farmer’s Daughter, Andreotti Family Farms Pumpkin Patch, Farmer John’s Pumpkin Farm, and Bob’s Vegetable Stand & Pumpkin Farm… among others!
Halloween Attractions and Haunted Houses
October Season | Bay Area locations
Family-friendly options include local Belmont Boo Bash, while thrill-seekers can visit Grimm's Hollow (San Jose), Fear Overload Scream Park (Newark), Winchester Mystery House haunted hotel experience (San Jose), and Tricks and Treats at Great America (Santa Clara).
Fall Foliage and Nature Viewing
October-November Peak Season | Peninsula and Bay Area locations
Best local spots include Sawyer Camp Trail (Peninsula), Woodside's Filoli Gardens, Japanese Tea Garden and SF Botanical Garden (San Francisco), Hakone Estate and Gardens (Saratoga), and Henry W. Coe State Park (South Bay). Sonoma County offers wine-country fall colors for day trips.
San Francisco Fall Events
September-October | San Francisco venues
Easy access from Peninsula communities to SF Chinatown Autumn Moon Festival (September 27-28), Hardly Strictly Bluegrass music festival (October 3-5, Golden Gate Park), and San Francisco Fleet Week (October 5-13). Perfect day trips that showcase the convenience of Mid-Peninsula living.
Bonus: San Carlos Holiday Season Preview
December 5, 2025, 5:00-8:30 PM | Laurel Street, San Carlos
15th Annual Night of Holiday Lights featuring family activities, carolers, arts and crafts, beer and wine sales, hot chocolate, holiday show, festive lights, and live musical performances. Free community event that extends the festive season into winter.
These seasonal activities perfectly complement the area's year-round charm and why so many families choose to make their home in communities like San Mateo, Menlo Park, and Atherton.
It’s not just the fall colors - this time of year presents one of the year's peak seasons for real estate activity in San Carlos and the Mid-Peninsula.
The region’s year-round pleasant weather means our real estate market stays active through autumn. For sellers, this presents an opportunity to capitalize on strong buyer demand while showcasing their homes during a particularly beautiful season. Properties with outdoor spaces often shine during the fall.
Thinking of selling your home this fall? Preparing for fall listings should focus on enhancing curb appeal and addressing any deferred maintenance. Our past home sales are a great example of how well-prepared, well-priced properties in local communities like Menlo Park, Atherton, and San Mateo can perform well during autumn months.
Fall home buyers benefit from motivated sellers and the opportunity to experience local communities during their most active season. Getting pre-approved with a lender and exploring our home search listings are a good first step to get a sense for the market and what’s in your price range.
There's something magical about fall in San Carlos and the Mid-Peninsula. Maybe it's sipping beer at Oktoberfest while the kids do the chicken dance, or finding the perfect pumpkin after a scenic drive to Half Moon Bay. Whatever draws you in, this season really shows off why so many families fall in love with life here.
If you're thinking about moving to the area, fall is honestly the best time to get a real feel for these communities. You'll see neighbors chatting at the Art & Wine Faire, kids racing around at the Water Dog Run, and families making memories at every turn. It's this genuine community spirit, plus great schools and year-round beautiful weather, that keeps drawing people to places like Burlingame, Hillsborough, and Redwood Shores.
Considering a real estate move this fall? We get it - it's exciting and maybe a little overwhelming. That's where we come in. We know these neighborhoods inside and out, and we genuinely care about helping families find their perfect fit. Through our Change Homes Change Lives program, we even support causes that matter to our clients, because being part of this community means more than just closing deals.
Ready to explore what the Mid-Peninsula has to offer? Let's chat about your fall real estate goals and how we can help make your Peninsula dreams happen.
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