Hi parents,
October is here, and the Bay Area is finally starting to feel a little more fall-ish. 🎃
This weekend has a particularly good mix: boats and marine science in Redwood City, free museum days, outdoor Shakespeare on the Coastside, music in Golden Gate Park, and the official beginning of pumpkin-patch season.
And because choosing a pumpkin patch can somehow become its own research project, I added a little guide below. Pick the version of fall your family is in the mood for and call it a day.
⭐ Weekend Pick
PortFest 2026
Saturday • 10:30 am–3:30 pm | 📍 Port of Redwood City
This one has a little bit of everything. Climb aboard a Marine Science Institute research vessel, try kayaking or stand-up paddleboarding, explore Redwood City’s working waterfront, and stop for hands-on kids activities and live music along the way.
A great mixed-age outing, especially for kids who love boats, science, or just being near the water.
All ages | Free | Get details
Happening All Weekend
Hardly Strictly Bluegrass
Friday–Sunday • Performances through 7:00 pm | 📍 Golden Gate Park, San Francisco
One of San Francisco’s biggest free music weekends returns with 70+ artists across six stages, including Mavis Staples, Los Lobos, Emmylou Harris, Robert Plant with Saving Grace, Molly Tuttle and plenty more.
With kids, I’d treat this as a pick-a-few-sets-and-settle-in outing rather than trying to cover the whole festival. Bring layers, snacks and a blanket, and public transit is strongly encouraged.
All ages | Free | Get details
Shakespeare in the Park: The Winter’s Tale
Saturday & Sunday • 2:00–4:00 pm | 📍 John L. Carter Park, Half Moon Bay
Half Moon Bay Shakespeare Company brings The Winter’s Tale outdoors for an afternoon performance in the park. Bring low chairs, settle into the amphitheater, and pair it with a pumpkin-patch stop for a very Coastside fall day.
Best for older kids who can sit through a two-hour performance | Free; donations welcome | Get details
Friday, Oct. 2
Free First Friday at the San Mateo County History Museum
10:00 am–4:00 pm | 📍 Redwood City
Free museum admission all day, with additional family programming including a preschool craft and storytime at 11:00 am. An easy indoor option if you have a younger child home during the day.
All ages; morning program best for preschoolers | Free | Learn more
Aguacate Music Kids
10:30–11:15 am | 📍 Foster City Library
A joyful interactive music session where little ones can sing, dance, play instruments and move together. This one is especially nice for the preschool crowd.
Ages 0–5 | Free | Get details
First Friday Nights at CuriOdyssey
5:00–8:00 pm | 📍 CuriOdyssey, San Mateo
If Friday night needs an easy plan, CuriOdyssey stays open late for its monthly family night. Explore the science exhibits and animals after hours without committing to a whole weekend day.
Families | Regular admission applies | Get details
Saturday, Oct. 3
Home Depot Kids Workshop: Witch Candy Box
9:00 am–12:00 pm | 📍 Participating Home Depot locations
October’s free build is appropriately Halloween-y: kids get to make their own wooden witch candy box and take it home. A simple morning activity before heading elsewhere for the day.
Best for ages 5–12; younger kids may need more help | Free | Register
African Arts Festival
11:00 am–4:00 pm | 📍 Yerba Buena Gardens, San Francisco
Live music and dance from across Africa and the African diaspora fill the Great Lawn, with interactive dance and drum lessons, face painting and food vendors alongside the performances.
This is my SF pick if you want something festive but more contained than Hardly Strictly.
All ages | Free | Get details
Maker Hangout
2:00–4:00 pm | 📍 Belmont Library
A low-key afternoon for kids who would rather make something than attend a big festival. Drop in and explore the library’s maker tools with projects that can range from crafty to techy.
All ages | Free; drop-in | Get details
Movies in the Park: The Princess Bride
7:30 pm | 📍 John L. Carter Park, Half Moon Bay
Bring blankets, layers and something warm to drink for an outdoor screening of The Princess Bride. If you’re already heading Coastside for pumpkins, this could turn the outing into a full fall day.
Families; best for school-age kids+ | Free | Get details
Sunday, Oct. 4
Sensory Sunday at Magical Bridge Playground
10:00 am–2:00 pm | 📍 Magical Bridge Playground, Palo Alto
Stanford Autism Center is hosting an inclusive morning of play, connection and sensory-friendly activities at Magical Bridge. Siblings and friends are welcome too, making this an especially thoughtful family outing.
All ages | Free; registration encouraged | Get details
Asian Art Museum Free First Sunday
10:00 am–5:00 pm | 📍 Asian Art Museum, San Francisco
General admission is free on the first Sunday of every month. Wander the galleries at your own pace and look out for hands-on artmaking, storytelling and other family-friendly programming throughout the day.
All ages | Free general admission; some special exhibitions extra | Get details
Bike Palo Alto
1:00–3:00 pm | 📍 Fairmeadow Elementary School, Palo Alto
Bring the bikes for a very practical kind of family adventure. Get help with helmet fitting, route planning and mini bike tune-ups, then choose a self-guided route and head out for a ride together.
All ages and riding levels | Free | Get details
🎃 Fall Is Here: Pick Your Pumpkin Patch
Pumpkin-patch season has officially arrived. Instead of giving you a giant list, here are four depending on what kind of outing you’re looking for.
For the full fall day: Rancho Siempre Verde
📍 Pescadero
This is the one when the pumpkin patch is the outing. Pick pumpkins and flowers, take a tractor ride, swing from giant tree swings, zoom down the tube slide, picnic overlooking the ocean and take home farm-grown apples.
Admission is per car and includes up to six guests plus five pumpkins, a bouquet of flowers, apples and the farm activities.
For maximum kid entertainment: Lemos Farm
📍 Half Moon Bay
Train rides, hay rides, pony rides, a petting zoo, slides, barn jumpers, a haunted house and, yes, pumpkins. If your kids want activities more than a peaceful stroll through a pumpkin field, this is probably your patch.
For pumpkins + a real farm feel: Andreotti Family Farms
📍 Half Moon Bay
A three-generation family farm where the pumpkins are actually grown on the property. Along with the pumpkin patch, fall brings a corn maze and hay rides. A nice middle ground between simply buying a pumpkin and the full amusement-park experience.
For the classic pumpkin-patch experience: Arata’s Pumpkin Farm
📍 Half Moon Bay
One of the Coastside classics, around since 1932. Come for pumpkins in all shapes and colors and stay for the distinctly old-school Half Moon Bay fall atmosphere.
Coastside tip: October traffic can get very real. Go early if you can, and avoid trying to squeeze three pumpkin patches into one day. One good patch + lunch or the beach is plenty.
🍂 Little Joy
Make it a pumpkin + beach day.
If you’re heading to Half Moon Bay anyway, leave a little unscheduled space.
Pick your pumpkins, grab something to eat, then head toward the coast for an hour with no agenda. October is one of those months when the outing between the outings can end up being the part everyone remembers.
Have a lovely weekend,
Akriti
Parent Pocket Guide is a weekly roundup of family-friendly things to do around the San Francisco Peninsula and beyond. If someone in your parent group always asks, “What should we do this weekend?” feel free to send this their way.
A quick question for you 💛
I’ve been making Parent Pocket Guide for a little while now, and I’d love to know if it’s actually helping you plan your weekends.
Three very quick questions below. Your answers will help me figure out what’s worth keeping, changing, or doing more of.