On Thursday afternoons this October, the Schoolhouse Parking Lot at Town Center hosts the Farmers Market. The Portola Valley Library at the same address, 765 Portola Road, runs programs for toddlers in the morning and for older kids after school that same week. In November, Community Hall, also at Town Center, hosts the one Town social event left on the calendar before the holidays.
Portola Valley's fall happens at a few addresses along one road, and it gets shorter as the weeks go on. October is full, November has room for about one evening out, and the Town's November and December calendars don't list a Halloween event or a tree lighting. Here is what's on, in order, from the busiest stretch to the quietest.
The week of October 13 at 765 Portola Road
This is the town's busiest week of the season. Everything in the table below happens at Town Center, between the library and the Schoolhouse lot.
| Day | Time | What | Where at 765 Portola Road |
|---|---|---|---|
| Tue, Oct 13 | 10:30–11:00 a.m. | Spanish Bilingual Storytime, Hora de Cuentos Bilingüe | Portola Valley Library |
| Tue, Oct 13 | 3:30–5:00 p.m. | Traditional Copal Wood Alebrije Painting for Día de los Muertos | Portola Valley Library |
| Wed, Oct 14 | 10:30–11:15 a.m. | Stories of Light: Celebrating Diwali | Portola Valley Library |
| Wed, Oct 14 | 2:00–3:00 p.m. | 3D Print and Paint | Portola Valley Library |
| Thu, Oct 15 | 10:30–11:00 a.m. | Baby Bounce Storytime | Portola Valley Library |
| Thu, Oct 15 | 2:00 p.m. | Farmers Market | Schoolhouse Parking Lot |
| Thu, Oct 15 | 3:30–4:30 p.m. | Reading Buddies | Portola Valley Library |
| Fri, Oct 16 | 10:00–11:00 a.m. | Tai Chi | Portola Valley Library |
| Fri, Oct 16 | 11:00 a.m.–1:00 p.m. | Mahjong | Portola Valley Library |
On Thursday the 15th, you can do the market and a library program in a single trip. The market opens at 2 p.m. and Reading Buddies starts at 3:30 p.m., in the same complex. The San Mateo County Libraries event page for the Portola Valley branch carries the full list. Some of these programs are tied to holidays and won't come back until next year.
The Thursday market runs all year
Several items on this calendar end on or before October 31. The Thursday Farmers Market doesn't. The Town's calendar lists it at 2 p.m. on October 15, 22 and 29, and the state's certified-market record lists the 765 Portola Road market as running year-round on Thursdays.
The two sources give different closing times. The Town's October 15 listing says 2 to 6 p.m. The California Department of Food and Agriculture's certified-market list, dated October 1, 2026, says 2 to 5 p.m. The 5 p.m. time is the safer one to plan around. With shorter days, the last hour of a late-afternoon market can be the first thing to go.
The vendor list is small and familiar. A Mercury News roundup of Bay Area farmers markets from July 2026 named Rojas Family Farms, Little Sky Bakery, The Baker Next Door and Esquivel Farms among the Portola Valley vendors. That list is from summer, so the fall lineup may differ.
Sunday the 18th: Christ Church
The first weekend event on this list is also on Portola Road, a few numbers up from Town Center. On Sunday, October 18, at 3 p.m., Christ Church Portola Valley and Woodside at 815 Portola Road hosts an "All-American Organ Recital" for the 250th anniversary of the United States.
The Almanac reported that four groups are presenting it together: the Palo Alto/Peninsula Chapter of the American Guild of Organists, the El Palo Alto Chapter of the Daughters of the American Revolution, the San Francisco Chapter of the Sons of the American Revolution, and the church itself. The organist is Barbara Baird, who taught at the University of Oregon for nearly 40 years.
All of the music is by American composers. The program includes "Concert Variations on the Star-Spangled Banner" and the "Battle Hymn of the Republic." It also has newer pieces, among them Noel Goemanne's "Partita on 'Simple Gifts,'" Joe Utterback's jazz-influenced setting of "Shall We Gather at the River," and Sharon J. Willis's "We Shall Overcome: A Suite for Solo Organ." A Sons of the American Revolution color guard in Revolutionary War uniform opens the event with a procession. The suggested donation is $20.
Sunday the 25th: Windy Hill
A week later, the season moves outdoors, and the starting point is still on Portola Road. The Midpeninsula Regional Open Space District is leading a guided Autumnal Beauty Loop Hike at Windy Hill Preserve on Sunday, October 25, from 8 a.m. to 1:30 p.m. The route is 7.5 miles. The group meets at the preserve's lower parking area on Portola Road, and Midpen says that lot fills quickly.
Windy Hill's preserve page currently shows no trail closures. Coal Creek, the other preserve close to town, has a longer closure, covered further down.
The Alpine Road deadline
The one fall attraction off Portola Road has the firmest end date. Webb Ranch Pumpkin Patch at 2718 Alpine Road is open daily from 10 a.m. to 6 p.m. through October 31, and its activity area closes at 5 p.m. The exception is Wednesday, October 14, when the activity area closes at 3:30 p.m. for a private event. InMenlo's season announcement gives the details. Shopping for pumpkins costs nothing and parking is free. The activity area requires a reservation on October weekends.
Weekend food vendors are Grillzillas, Tlaxiaco's Pizza and Mister Softee. Three weekends are left in the patch's season: October 17–18, 24–25 and 31. The 31st is a Saturday, so the season ends on a weekend day that requires an activity reservation. Buying pumpkins only on a weekday, such as after a Thursday market run, needs no reservation and no admission.
The trail that's resting until spring
At Coal Creek Preserve, the Meadow Trail has been closed since April 27, 2026, for drainage and tread improvements. The closure runs into spring. Midpen's trail conditions page gives the end date as April 5, 2027, in one place and April 7, 2027, in another. The rest of the preserve's trails stay open.
Midpen's reason for the length of the closure matters for this season. The new trail work needs to rest and "settle in" over the rainy season, so the soil of the trail bed can compact and firm up again before foot and bicycle traffic returns. As a result, the Meadow Trail is off-limits for this entire fall and winter, even on dry days. A Coal Creek walk this season has to use the preserve's other trails.
November has one evening on the calendar
After October, the Town calendar empties out. The November and December views don't list a Halloween event, a tree lighting or another standalone holiday gathering through early December. The Star Party ran on October 2, and the October Nature and Science Committee meeting was on the 8th. Both are already past.
That leaves Portola Valley Trivia Night, hosted by the Parks and Recreation Committee, on Saturday, November 14, from 6:30 to 9 p.m. at Community Hall, 765 Portola Road. Trivia begins at 7 p.m. The Town's Trivia Night page says space is limited to 16 teams of up to eight people each. That works out to at most 128 players at the only Town social event on the November calendar. Groups that want a spot should register early, or plan a full team of eight so every seat counts.
At The ReSolve Group, we follow Portola Valley's calendar the way residents do, one Thursday market and one Town Center evening at a time. If questions about your home come up between now and the Trivia Night sign-up, we're glad to talk them through calmly and without any pressure.