Bay Meadows October Agenda

October brings crisp fall days, festive nights, and plenty of reasons to explore the Peninsula. From pumpkin season and Halloween celebrations to outdoor markets, art festivals, hands-on workshops, and community traditions, the calendar is packed with ways to celebrate autumn close to Bay Meadows.

Get into the spirit with Nightfall at Filoli, the Half Moon Bay Art & Pumpkin Festival, haunted happenings at Hiller Aviation Museum, and trick-or-treating throughout the Peninsula. Or slow things down with a farmers market stroll, a scenic hike, a baking class, or a Saturday spent browsing local makers. With so much happening in San Mateo and beyond, October is the perfect time to get out, connect, and enjoy everything the season has to offer. We want to see your season! Show us your spooky decorated stoops, the stunning colors of our neighborhood landscape, your fall harvest in Persimmon Park, plus favorite seasonal sips at Blue Bottle Café and bites in Town Square.

Be sure to invite us to collaborate and tag us at @baymeadowslife in your autumn Instagram photos this fall.

When you live just steps from Caltrain, getting from here to there is easy and car-free. Grab the Hillsdale Caltrain schedule and dive into our monthly event roundup to discover all the ways to celebrate, create, explore, and connect throughout the month ahead.

Bay Meadows Run Club with Basecamp San Mateo. Join this free fun run Wednesday evenings at 6pm and Saturday mornings at 8am. Meet at 3050 S. Delaware for a 2-, 3-, 4- or 6-mile loop (something for everyone) to get moving. Run, jog, or walk. Happening weekly – rain or shine. All paces and people are welcome. Members often gather in Town Square for a Blue Bottle coffee or at Fieldwork Brewing Beer Garden after each run. Plus, there’s no fee! You heard right – membership is not required. This is a community building fun run, compliments of our neighbors at Basecamp Bay Meadows.

Sunday Downtown San Mateo Farmers Market. West Coast Farmer’s market runs year-round at 222 East 4th Avenue Sundays from 9am to 2pm in Downtown San Mateo. The farmer’s market has a curated selection of fresh fruits, veggies, and a couple of tasty food trucks to fuel your morning stroll.

College of San Mateo Farmers’ Market. Shop seasonally and fresh each Saturday from 9am to 1pm (year-round) at San Mateo’s largest farmer’s market located at 1700 West Hillsdale Boulevard.

The 25th Avenue in San Mateo Farmers’ Market. May through October 20 on Tuesdays from 3pm to 7 pm, this farmers market is an easy walk or bike ride from Bay Meadows (~0.8 mi), bringing the best Peninsula produce and makers moments from your door.

October 1- Nov 13, Cans for Change by Rise by Bozzuto. 🍁In the spirit of giving back, Rise by Bozzuto’s mission is to tackle hunger this holiday season. 🥫Join The Apartment Collection at Bay Meadows as they host a food drive to collect canned goods to support the San Francisco Marin Food Bank. Starting, Thursday, October 1st, through Friday, November 13th, you will have the opportunity to drop off your donations.

Participating is as easy as purchasing new, unopened canned goods and dropping them off in The Russell Leasing Office.

📍 3098 Kyne Street West, San Mateo, CA 94403
650-855-8768 | BayMeadows@bozzuto.com

October 2, First Friday Nights. On the first Friday of every month, from 5 PM until 8 PM, parents and kids celebrate together at CuriOdyssey in San Mateo. Dance to some of your favorite hits, while enjoying animal presentations and science activities.

October 2, Movies in the Park. Catch School of Rock under the stars at Barrett Community Center in Belmont, with movie snacks, raffle prizes, and plenty of outdoor movie night fun.

October 2, San Mateo County History Museum FREE First Fridays. Visit the SMCHM every Friday for free First Friday events, where children enjoy special programs including crafts and storytime, and adults can join a docent-led tour of the museum.

October 4, Autumn Succulent Terrarium Workshop. Create a festive pumpkin-shaped succulent terrarium, perfect for your autumn décor, at this hands-on seasonal workshop in San Mateo.

October 6, Marsh Hike at Coyote Point. Explore Coyote Point’s vibrant wetlands in San Mateo on a guided CuriOdyssey hike featuring native plants, local wildlife, and seasonal discoveries.

October 10 & 11, San Carlos Art & Wine Faire. Discover handcrafted art, local flavors, wine, brews, live entertainment, and family fun at the 34th Annual Art & Wine Faire in downtown San Carlos.

October 11, Croissant & Pain au Chocolat. Learn the art of classic French croissants and pain au chocolat in a hands-on baking class at Baking Arts in San Mateo.

October 17, HEAD WEST Marketplace. Spend the day exploring Downtown San Mateo’s B Street during the HEAD WEST Marketplace, where you can shop handcrafted goods from local makers and artists while enjoying the neighborhood’s vibrant retail shops and dining scene.

October 17–18, Half Moon Bay Art & Pumpkin Festival. Celebrate fall at the 54th Annual Half Moon Bay Art & Pumpkin Festival, kicking off with the legendary World Championship Pumpkin Weigh-Off.

October 23-November 1, Halloween Haunted Hangar. Come in costume and see the Gallery decked out in its spooky Halloween decorations and the “Great Pumpkin” Scavenger Hunt at the Hiller in San Carlos.

October 24, Belmont Centennial Fest. Celebrate Belmont’s 100th birthday at Twin Pines Park with a car parade and show, live music, food trucks, games, a time capsule ceremony, and an evening drone show.

October 24, Boos and Brews on B Street.Celebrate Halloween at Boos on B Street in Downtown San Mateo with trick-or-treating, crafts, music, food, and festive photo ops along the B Street Pedestrian Mall.

October 24, Halloween Spooktacular. Enjoy a spooktacular day in Redwood City with carnival games, a monster maze, creepy crafts, a haunted ambulance, mini pumpkin patch, prizes, and more Halloween fun.

October 28, Belmont Boo Bash. Celebrate Halloween at Belmont’s Boo Bash with Trunk or Treat, a haunted house, live music, food trucks, and festive fun for all ages in Belmont.

October 29, Trunk or Treat. Get ready for a spooktacular evening at the Hiller Aviation Museum’s Trunk or Treat in San Carlos, part of our annual Halloween Haunted Hangar celebration.

October 31, Doggoween at Bay Meadows. It’s back! And, it’s on Halloween! Get your dogs in costume and head to our neighborhood beer garden at Fieldwork Brewing San Mateo for a chance to WIN. The whole community comes together for this annual event. Follow Fieldwork_SanMateo and BayMeadowsLife on Instagram for more information.

October 31, Pumpkin Drop.Join a special celebration of Halloween excitement as the Hiller Aviation Museum’s witch drops her doomed pumpkin from a high flying helicopter at the Hiller in San Carlos!

Thru November 1, Nightfall. Step into Filoli after dark for a haunting Halloween adventure filled with pumpkins, firelight, mysterious clues, an enchanted mansion, glowing woodlands, and a hidden witch’s village.

Sep-Oct Sessions at Clayroom. When signing up for 6-week classes, one signs up by selecting (signing up for) the 1st class. Classes 2-6 will occur on a weekly cadence during the same day of the week and timeslot. 6-week in-studio classes for pottery.

Discount Tuesday (at Cinemark Century San Mateo 12). There’s never been a better time to turn up on a weekday, because every Tuesday at Cinemark is Discount Tuesday—cheap movie tickets are always within reach.

Bel Mateo Bowl Friday, Saturday and Sundays in San Mateo.
Karoake – Fridays from 7:30 – 11:30pm hit the mic with friends for some Karaoke.
Planet Bowling – Bowl in the dark under black lights on Fridays from 9:30 – 11:30pm and Saturdays from 8- 11:30pm.
Incredibowl – Fridays 9:30 – 11:30pm and Saturdays from 8 – 11:30pm interactive graphics elevate your bowling game with Incredibowl.
Family Pizza Night – Sundays from 5-8pm Family Pizza Nights and all you can bowl 8-10pm!
All You Can Bowl – Sundays enjoy unlimited bowling for 2 hours 8- 10pm! 

Bicycle Sundays. From 9am – 3pm, a 3.8-mile segment of Cañada Road along Crystal Springs Regional Trail is closed between the Filoli entrance and Highway 92 allowing for non-motorized activities including jogging, bicycling, hiking, roller-skating, and walking. Cañada Road between Edgewood Road to the Filoli entrance will remain open to vehicles. Check for holiday closures.

Experience Midurban life. Bay Meadows is a family-friendly neighborhood with lots of open space to enjoy all-year long. Whether it’s growing your own vegetables in an organic community garden, playing a game of pick-up basketball after work, team building over bocce in the beer garden, picnicking with family on warm summer nights or with a run around the park, there’s no shortage of green space to explore. Check out life out and about at Bay Meadows by following us on Instagram.

Bay Meadows April Agenda

Spring has officially sprung in the Bay Meadows neighborhood, and April is bursting with fresh-air fun, festive traditions, and family-friendly adventures. From sweet Easter celebrations and creative workshops to outdoor strolls, hands-on classes, and community events, there’s something happening every week to keep everyone entertained. Whether you’re decorating cookies with the kids, snapping photos with the Easter Bunny, or exploring local parks and pop-ups, this month is all about making the most of the season and creating memorable moments together.

When you live just steps from Caltrain, getting from here to there is easy—and car-free. Grab the Hillsdale Caltrain schedule and dive into our monthly event roundup to discover all the ways to celebrate, create, explore, and connect throughout the month ahead.

Bay Meadows Run Club with Basecamp San Mateo. Join this free fun run Wednesday evenings at 6pm and Saturday mornings at 8am. Meet at 3050 S. Delaware for a 2-, 3-, 4- or 6-mile loop (something for everyone) to get moving. Run, jog, or walk. Happening weekly – rain or shine. All paces and people are welcome. Members often gather in Town Square for a Blue Bottle coffee or at Fieldwork Brewing Beer Garden after each run. Plus, there’s no fee! You heard right – membership is not required. This is a community building fun run, compliments of our neighbors at Basecamp Bay Meadows.

Sunday Downtown San Mateo Farmers Market. West Coast Farmer’s market runs year-round at 222 East 4th Avenue Sundays from 9am to 2pm in Downtown San Mateo. The farmer’s market has a curated selection of fresh fruits, veggies, and a couple of tasty food trucks to fuel your morning stroll.

College of San Mateo Farmers’ Market. Shop seasonally and fresh each Saturday from 9am to 1pm (year-round) at San Mateo’s largest farmer’s market located at 1700 West Hillsdale Boulevard.

The 25th Avenue in San Mateo Farmers’ Market returns in May!

April 1, Foster City Night Market by Off The Grid – Every Weds 5 to 9 pm. Ride your bikes from Bay Meadows to the Foster City Lagoon for a fun time! Running each Weds weekly through October 2026, just adjacent to Bay Meadows San Mateo in nearby Foster City, Off The Grid is bringing live entertainment and delicious mobile food options to the beautiful Leo Ryan Park meadow! Pet and family friendly with live entertainment. Read all about it HERE.

April 1, Easter Egg Cookie Decorating Workshop with Mrs. Fields. A fun springtime activity perfect for kids and families at the Hillsdale Shopping Center in San Mateo. The first 100 children will get to decorate an egg-shaped chocolate chip cookie with colorful frosting and sprinkles to take home.

April 1-4, Photos with the Easter Bunny. The Easter Bunny is hopping back into Macy’s Center Court at the Hillsdale Shopping Center for springtime photo fun from 11am–7pm daily! Bring the whole family and capture sweet seasonal memories with everyone’s favorite fluffy friend.

April 1-12, Downtown Parcade- Mini Golf & Arcade. This 18-hole mini golf course in Redwood City is ready to play, complete with glow-in-the-dark nighttime rounds for an extra challenge. Come sink a hole-in-one, battle for bragging rights, or just press play on a good time, the Parcade is open and ready. Game on!

April 2, Pysanky Egg Dyeing. This popular class is back for another spring in Redwood City! Natalie of Salayi Designs will walk you through Pysanky wax resistant egg dyeing to make your own ornate and colorful eggs for Easter or whatever your pleasure.

April 3, First Friday Nights. On the first Friday of every month parents and kids celebrate together at CuriOdyssey in San Mateo. Swing into the weekend with music, food trucks, animals, and fun!

April 3, San Mateo County History Museum FREE First Fridays. Visit the SMCHM every Friday for free First Friday events, where children enjoy special programs including crafts and storytime, and adults can join a docent-led tour of the museum.

April 4, Eggstravaganza! Eggstravaganza returns for it’s 49th year to Central Park in San Mateo! Join the spring bunny for this eggcellent family-fun spring-themed event. Enjoy kid-friendly activities, live entertainment, egg hunts, and more.

April 4, Easter Bunny Arrives by Helicopter! Get an Easter Egg straight from the Bunny and enjoy face painting, a bounce house and slide, and a model train display at Hiller Aviation Museum in San Carlos.

April 4, Egg Adventure Hunt. Join the annual Egg Adventure Hunt in Belmont where 20,000 eggs and 4 golden eggs will be hidden throughout the park for ages 3-10. Stick around after the hunt to enjoy refreshments and snap photos with the bunny.

April 5, Gratitude Meditation. Whether you are a seasoned meditator or a beginner, this gathering at Chill Spot Rendezvous in San Mateo will provide valuable connection, calming peace, and positivity. Tickets include a free scoop of ultra-premium gourmet ice cream or specialty drink.

April 7, Walk Across Bay Meadows. Enjoy a level, paved walk along two duck ponds, around the meadow, and through beautifully landscaped urban community spaces and gardens. This gentle stroll is a wonderful way to get some fresh air, chat with friends, and appreciate the scenery together.

April 9, Spring Flower Arranging. Grab some friends and have fun with flowers in Woodside. In this laid-back, hands-on experience, Filoli’s Floriculture team will show you how to turn fresh spring blooms and greenery into a gorgeous arrangement to take home.

April 11-12, Heads Up: Expressive Wall-Hanging Heads. Join Clayroom in San Mateo with ceramics artist Kyungmin Park for a two-day workshop focused on creating expressive wall-hanging ceramic heads. All levels are welcome, and no prior figurative sculpture experience is required.

April 12, Airport Runway Run. Don’t miss this rare chance to run on the real Runway at San Carlos Airport. Certified 5K/10K with 2K fun run.

April 12, Visit A Working Regenerative Farm In Woodside. Enjoy a working regenerative farm. Mission Farm is committed to soil health and therefore they use regenerative practices.

April 18, Earth Day 2026. This is a fantastic opportunity to learn about environmental resources and discover ways to enhance sustainability in the community at Twin Pines Park in Belmont.

April 19, Earth Day. Celebrate Earth Day with the City of San Carlos from 9:00 a.m. to 1:00 p.m. at the Wheeler Plaza Parking Lot on Laurel Street.

April 23–May 3, Taste of the Peninsula. Explore the culinary landscape of San Mateo County at this week of special prix fixe menus at hundreds of restaurants. The first half of the festival will focus on the San Francisco Peninsula’s “bayside” restaurants while the second half on the area’s “coastside.”

April 25, City Nature Challenge. Enjoy a public marsh hike at Coyote Point and help catalog plants and animals using iNaturalist. Your observations help scientists better understand the ecosystems around us. Bring your curiosity, your camera, and your sense of discovery.

April 26, Neapolitan Style Pizza. Learn how to make a classic pizza made with hand stretched dough in the Neapolitan style at Baking Arts & Coffee in San Mateo.

April/May Sessions at Clayroom. When signing up for 6-week classes, one signs up by selecting (signing up for) the 1st class. Classes 2-6 will occur on a weekly cadence during the same day of the week and timeslot. 6-week in-studio classes for pottery.

Discount Tuesday (at Cinemark Century San Mateo 12). There’s never been a better time to turn up on a weekday, because every Tuesday at Cinemark is Discount Tuesday—cheap movie tickets are always within reach.

Bel Mateo Bowl Friday, Saturday and Sundays in San Mateo.
Karoake – Fridays from 7:30 – 11:30pm hit the mic with friends for some Karaoke.
Planet Bowling – Bowl in the dark under black lights on Fridays from 9:30 – 11:30pm and Saturdays from 8- 11:30pm.
Incredibowl – Fridays 9:30 – 11:30pm and Saturdays from 8 – 11:30pm interactive graphics elevate your bowling game with Incredibowl.
Family Pizza Night – Sundays from 5-8pm Family Pizza Nights and all you can bowl 8-10pm!
All You Can Bowl – Sundays enjoy unlimited bowling for 2 hours 8- 10pm! 

Bicycle Sundays. From 9am – 3pm, a 3.8-mile segment of Cañada Road along Crystal Springs Regional Trail is closed between the Filoli entrance and Highway 92 allowing for non-motorized activities including jogging, bicycling, hiking, roller-skating, and walking. Cañada Road between Edgewood Road to the Filoli entrance will remain open to vehicles. Check for holiday closures.

Experience Midurban life. Bay Meadows is a family-friendly neighborhood with lots of open space to enjoy all-year long. Whether it’s growing your own vegetables in an organic community garden, playing a game of pick-up basketball after work, team building over bocce in the beer garden, picnicking with family on warm summer nights or with a run around the park, there’s no shortage of green space to explore. Check out life out and about at Bay Meadows by following us on Instagram.