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Orchard Days at Filoli in Woodside offer live music, local artists, food and activities every weekend through October. Courtesy Filoli.
Orchard Days at Filoli in Woodside offer live music, local artists, food and activities every weekend through October. Courtesy Filoli.

Autumn is finally here. The Peninsula’s temperate climate and proximity to the beautiful Santa Cruz Mountains offer boundless opportunities to get outside and explore the great outdoors. Trail running and biking are among the popular outdoor activities for local residents looking to enjoy the beautiful weather while getting a great workout. If strolling is more your speed, there are also plenty of chances to enjoy the fall weather at a leisurely pace.

We’ve rounded up a few upcoming events that will get your blood pumping, and earn all the pumpkin-spiced treats coming your way — plus some more laid-back ways to enjoy the perfect fall weather.

Trail runs and bike rides

Historic Los Altos Bike Tour Oct. 14: Meet at the Los Altos History Museum, bike eight miles around town to see the best historic sites and homes in Los Altos, hear some stories from Los Altan of the Year Gary Hedden, then head back to the Museum for an optional $12 lunch.

Bike Tour of Historic Los Altos Saturday, Oct.14, meeting at the Los Altos History Museum, 51 S. San Antonio Road, Los Altos. eventbrite.com.

45th Annual Pumpkin Run Oct.15: There are few places in the 650 that one associates with “pumpkin” more than the coastal community of Half Moon Bay. Throughout the month of October, gourd-themed events take place in and around the town. The Great Pumpkin Run is a wonderful trail race that offers fantastic Pacific Ocean views. All proceeds benefit Senior Coastsiders, a local nonprofit dedicated to supporting successful aging for Coastside seniors.

Great Pumpkin Run Sunday, Oct. 15, starting at Hatch Elementary School, 490 Miramontes Ave., Half Moon Bay. Race distances vary: Kids Fun Run, 5K, 10K, and Half Marathon. pumpkinfest.miramarevents.com.

Woodside Trail Run Nov. 4: Run through the beautiful shaded trails of Huddart and Wunderlich Parks in the foothills of the Santa Cruz Mountains. This is a magical trail run on soft dirt trails, alongside lush ferns and a fairytale forest. Choose from several race distances and prepare for an unforgettable trail race adventure!

Woodside Trail Race Saturday, Nov. 4, starting at 1100 Kings Mountain Road, Woodside. Distances include 10K, Half Marathon, 35K and 50K. runsignup.com.

Thanksgiving Fundracer Relay Nov. 19: If you are more of a pack runner than a solo strider, check out Pacifica Runner Thanksgiving Fundracer Relay, benefitting the Pacifica Resource Center. Teams of two-to-four adults and youth compete in a four-mile relay. Prizes will be given for best performance and best costume categories.

Thanksgiving Fundracer Relay Sunday, Nov. 19, starting at Terra Nova High School, 1450 Terra Nova Blvd., Pacifica. pacificarunners.wildapricot.org.

Autumnal outings

Los Altos Wine Stroll Oct. 13: One of the most anticipated events on the Los Altos social calendar is almost here. Tickets are on sale now for this evening stroll through downtown Los Altos, with participants visiting a variety of high-end boutiques, galleries, and retailers while imbibing samples from some of the finest wineries in the area. The perfect date night, or girls’ night out!

Los Altos Wine Stroll Friday, Oct. 13, downtown Los Altos. Advance ticket purchase required. downtownlosaltos.org.

Orchard Days at Filoli through Oct. 29: Enjoy the bounty of fall in Filoli’s Gentleman’s Orchard, where the jewel-tones of autumn surround live music, spiced cider, and good times spent together. Settle into the walnut grove with a cup of cider from the bar or an autumn treat from the pop-up cafe. Explore the historic trees, learn about harvest celebrations, and find fruitful fall fun every weekend!

Orchard Days at Filoli will be held Saturdays and Sundays through Oct. 29, Filoli Historic House and Gardens, 86 Cañada Road, Woodside. filoli.org.

The Old Barn at Djerassi on Sept. 25, 2022. Photo by Angela Swartz.
The Old Barn at Djerassi on Sept. 25, 2022. Photo by Angela Swartz.

Djerassi Sculpture Hikes through Nov. 26:

The Djerassi Resident Artists Program is offering guided hikes for nature and art lovers alike through Nov. 26. The program’s hike director and volunteers guide groups of up to 20 on a 3.5 mile trek through the 583-acre ranch, stopping by over 40 sculptures. The hikes take place every Sunday.

Djerassi Sculpture Hikes, Sundays 10 a.m.-1 p.m. at Djerassi Ranch, Woodside. Tickets are $50. Reservations required. djerassi.org.

Guided Geocache Hike October 14: Join Docent Naturalists Sarah Schoen and Joyce Tang to search for geocaches, or hidden treasures, using supplied GPS units at Los Trancos Preserve. This all-ages activity is an introduction to geocaching and is geared toward the first-time geocacher but all are welcome.

Mid-Peninsula Guided Geocache Hike Saturday, Oct. 14, meeting in the parking lot at Los Trancos Preserve, across the road from the Montebello Open Space Preserve Parking lot at 4301 Page Mill Road, Los Altos. Closed-toed shoes required. Reservations accepted through Oct. 13. openspace.org.

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1 Comment

  1. Please list and detail more outdoor activities that are free. It seems that all the highlighted ones have fees. Include some walks and other outings that are easy for those who walk somewhat slowly.

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