Bay Meadows

Get ready to roll through May in the Bay Meadows neighborhood and beyond! From fair days and makers’ markets to fun runs, farmers markets, and food truck round-ups, you’ll find something for everyone. Explore our curated agenda and map out your month!

May is bike month, and when bike trails and Caltrain are at your doorstep – it’s easy to get from here to ‘there’ car-free! Get the Hillsdale Caltrain schedule here.

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 welcomed. 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.

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. Seasonal Highlight: Garlic.

May 1-2, Spring Teas at Fioli. Kick-off the spring season with an elegant tea service in Filoli’s Garden House in Woodside – a truly unique setting located in the middle of Filoli’s 16-acre garden in full bloom. Indulge in a decadent-tiered tower with both savory and sweet delights while sipping tea and sparkling wine.

May 2, First Friday Nights. Swing into the weekend with live music, a food truck, animals, and fun at CuriOdyssey in San Mateo.

May 2, SMC History Museum First Fridays. Explore exhibits and enjoy additional special programs for children and adults including docent-led tours, story readings, craft projects and more in San Mateo.

May 3, Residential E-Waste and Shredding Event. Saturday, May 3, 2025 @ 9:00 am – 12:00 pm. Located in the Beresford Park parking lot. On-site secure shredding and e-waste recycling.

May 3, Asian American & Pacific Islander Heritage Month Celebration. Head to Central Park in San Mateo as they launch a vibrant new celebration honoring Asian American and Pacific Islander (AAPI) Heritage Month. There’ll be live demos, food trucks, arts and crafts and so much more.

May 4, San Mateo’s Plant Sale & Craft Fair. Plant lovers! Bring the family to the San Mateo Garden Center for live music, a plant sale, potting tables for large and small. Mix with garden club members and more.

May 4, iPhone Flower Photography. This San Mateo class will teach you to combine your love of flowers and your favorite new addiction – the iPhone.

May 5, Cinco de Mayo at Flores. Celebrate Cinco de Mayo at Flores in the Hillsdale Shopping Center in San Mateo, with live music from 4:30-7:30pm.

May 7, 14, 21, 28 Foster City Night Market by Off The Grid – 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 2025, 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.

May 10, Compost, Seeds & Seedling Giveaway! The City of San Mateo invites you to pick up FREE plant starts, seeds and compost while supplies last from 10 am to 2 pm at The Phoenix Garden (222 Paul Scannell Drive). Learn easy ways to reduce waste, get tips from master gardeners and learn how to support local pollinators. Visit here for more learning opportunities – County-wide.

May 10, Pinewood Derby. Ready! Set! Pinewood Derby returns to Hillsdale in San Mateo! Join The Boy Scouts of America as they host their annual Derby in Nordstrom Court.

May 11, Kids’ Carnival. Join the excitement with special activities just for kids at the Hiller in San Carlos. Paint the Cessna Cardinal, check out in an airplane or helicopter, and more!

May 14, Community Hikes. Enjoy a hike in Belmont’s Waterdog Lake & Open Spaces. Hikes will be led by recreation staff, and they will provide brochures on Belmont trails and wildflowers.

May 15, Bike to Work Day + Bike To Wherever Days. May is bike month! Show us how you roll @baymeadowslife. Tag us in your fun BTWD snaps, Reels and Stories! Thursday, May 15 is bike to work day and Bay Meadows makes it easy to get rolling! Grab a PUBLIC bike (the official bike of Bay Meadows) and show us how you roll. Take the pledge to ride all month long with our friends at the Silicon Valley Bicycle Coalition. You’ll find Energizer Stations in Santa Clara & San Mateo Counties on May 15, 16, and 17! This year, all nine Bay Area counties have come together to provide resources and rewards. You can find more info at Bay Area Bike to Work.

May 15, Celebrating Our Story. Join the County of San Mateo and the San Mateo County History Museum to celebrate the county’s 169th anniversary and dedicate the new 500 County Center office building.

May 16, Watercolor Garden Party in Woodside. Experience the magic of Filoli’s Garden through the eyes of Erin Gleeson, artist, chef, and New York Times bestselling author. In this immersive watercolor workshop, Erin will guide you in creating a stunning watercolor piece.

May 16-18, Hometown Days. Enjoy a special Centennial Year Celebration in San Calros with live entertainment, extended hours of fun, games, rides, and weekend-long activities and entertainment in Burton Park.

May 17, Clayroom San Mateo Member Art Show. San Mateo and SF Peninsula neighbors and friends are invited inside Clayroom San Mateo at Bay Meadows to shop the special art show with handcrafted items made by members. Light refreshments will be served from 4 to 5:30pm.

May 17, Weekend Workshop: Marine Marvels. Head to CuriOdyssey in San Mateo and dive into the fascinating world of marine animals and discover the amazing creatures that inhabit our oceans, from playful dolphins to mysterious deep-sea dwellers.

May 17, Friday Outdoor Movie Night. Up for some popcorn and a movie under the stars? Grab your friends, bring your blankets and lawn chairs, and enjoy a Teen Outdoor Movie Night in Redwood City.

May 17, Soul Stroll. The Bay Area Community Health Advisory Council invites you to join this 1, 3, 5 Mile Run/Walk and health fair at Coyote Point Recreation Area in San Mateo.

May 18, HEAD WEST Marketplace. Visit Downtown San Mateo’s South B Street every third Sunday of the month. Browse unique holiday gifts or find a treat for yourself from 50 local Makers, Merchants, Crafters, Designers, and Artists. While you’re here, explore over 100 of Downtown’s retail offerings, delicious dining destinations, and local art — there’s something for everyone this season. Runs through December.

May 26, Memorial Day MURPH Challenge with Basecamp San Mateo at Bay Meadows. Meet at 10:30 AM. FREE to all. No membership required.

May 30, Croissant and Pain Au Chocolat in San Mateo. Learn how to prepare melt-in-the-mouth all-butter croissants and pain au chocolat in the classic French method.

May 30-June 8, San Mateo County Fair. Enjoy live entertainment, competitive events, unique food, arts & educational exhibits, livestock and agricultural exhibits, and an exciting, fun-filled carnival for all ages.

May 31, BAY AREA BURN with Basecamp San Mateo at Bay Meadows.  Come join this exclusive San Mateo designed workout. There’ll be a pot luck, including spicy foods. Call the studio for drop-in rates!

May 31, San Mateo PAL’s 5K Run/Walk and Wellness Fair. Start the day with a 5K Run or Walk on the bay trail at Seal Point Park. Stay after to attend a free Wellness Fair.

May 31, Belmont Blooms. Join this gardening event at Barrett Community Center in Belmont.

Fogbird San Mateo Spring Monthly Mixology 101 Class. Learn bartending tips & tricks while shaking up three fan-favorite drinks: the Wimbledon, Bourbon in Bloom, and the classic Siesta. Enjoy delicious bites, good company, and leave with a keepsake recipe card to impress at home. Limited seats available, May & June Classes – dates coming soon!

May/June 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 time-slot. 6-week in-studio classes for pottery.

Family Pizza Night at Bel Mateo Bowl in San Mateo. 2 hours of bowling, use of rental shoes, 1 large one topping pizza per lane and 1 pitcher of soft drink per lane on Sundays. Elevate your Friday or Saturday night with Incredibowl with interactive graphics and games projected right on the lanes! These animations interact with the ball as it rolls down the lane for a whole new bowling experience.

Trivia Night: Every other Monday at Hillsdale. Gather your pals every other Monday from 6-8pm for Trivia Night hosted by Sandcastle Entertainment! Fantastic food, beer and fun at The Refuge.

Bicycle Sundays. 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. 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.