The Bay Meadows May Agenda

Get ready to enjoy a full month of May activities in the Bay Meadows neighborhood and beyond. May is bike month so get rolling! We’ve rounded up an agenda that includes fun ways to celebrate with Mom, SF Peninsula pottery and cooking classes, outdoor concerts, comedy and much, much more. When you live just steps from Caltrain it’s easy to get from here to ‘there’ car-free! Get the Hillsdale Caltrain schedule here. Explore our roundup and plan your month.

May is Bike Month. Show us How You Roll. Pledge to Ride. Bike Wherever! Download our Bay Meadows Bike Map and read all about the bicycle happenings this May.

Too Hot to Handle – Clayroom San Mateo Exhibit runs through May 15! Stop by Monday-Friday from 10-9 or Sat/Sun from 10-6 at 3050 South Delaware Street to view these extraordinary clay mugs hand crafted by our community.

Sign up now for May/June Sessions at Clayroom San Mateo at Bay Meadows. When signing up for 6-week classes at Clayroom San Mateo, 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.

Introducing the Basecamp San Mateo Run Club at Bay Meadows = Wed Evenings and Sat Mornings:

May 1, 4, 8, 11, 15, 18, 22, 25, 29, Bay Meadows Run Club. Wednesday evenings at 5:30pm and Saturday mornings at 8am. Meet at 3050 S. Delaware just beneath Survey Monkey’s HQ 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 after each run. Plus, there’s no fee! You heard right – membership is not required.

May 4, 11, 18, 25, 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. Bring a big shopping bag or two because the farmers’ tables are filled with the freshest spring fruits and vegetables like berries and spring greens to delightful gifts like cut flowers, local honey, jams and sauces, locally-made olive oil, and chocolates. Also find fresh eggs, grass-fed beef, cheeses, and seafood.

May 2, Cinco de Mayo at The Alexandria Center. Join The Alexandria’s Salt + Brine Restaurant for a Cinco De Mayo celebration with Tacos, Pinata, Chihuahua Races, Mezcal Tastings, a Mariachi band and more.

May 3, Bair Island Walking Tour. Learn about this beautiful post protected space and enjoy a 1-mile gentle/flat walking tour of Bair Island in Redwood City.

May 3, First Friday. The San Mateo County History Museum in Redwood City will be open without admission fees the first Friday of every month as part of its continuing “FREE First Fridays” program.

May 4, Take A Hike with SMC. This month’s San Mateo County ‘Take A Hike’ challenge hike is at Cowell-Purisima Trail from 9-11am. The routes for the in-person hiking events are the same as those for the 2024 challenge, so you can complete the challenge on your own or with the event attendees monthly.  Register here.

May 4, Happy San Mateo County Day. The SMC History Museum in Redwood City will celebrate the county’s 168th birthday. The theme for this year’s party is the 1940s with craft activities from the era.

May 4, Star Wars Party @ Blue Oak Brewing Co. Calling all Jedi, Sith, and intergalactic beings! Join Blue Oak Brewing for an epic Star Wars Party in San Carlos.

May 4, Cinco de Mayo Celebration. Experience the ultimate fiesta at Hillsdale in San Mateo, featuring a mesmerizing Ballet Folklorico, dance to the soulful melodies of a live mariachi band, plus kids activities.

May 4, Lobster Fest. Join the Rotary Club of Belmont and Redwood Shores for their annual Lobster Fest Fundraiser. Enjoy a lobster dinner, bar, silent and live auctions, music, and more.

May 5, ​All About Edible Herbs & Edible Flowers​. Discover or renew a new gardening excitement and learn the basics of growing, harvesting, and using culinary herbs and edible flowers in San Mateo.

May 7, The monthly Fieldwork Brewing San Mateo Pizza Party returns Tuesday, May 7 at 5pm! Every first Tuesday of the month, @fieldworkbrewing_sanmateo is throwing a pizza party in the Bay Meadows Beer Garden- $13, all you can eat pizza, 5-8pm or until the pizza is gone. Be there or be square (like the Detroit-style all-you-can-eat pizza)

May 7 + 19, lululemon Hillsdale Run Club. The first Tuesday evening of every month + the third Sunday morning join the local lululemon team in San Mateo. From beginners to experts, strollers to dogs or babies, there’s a place for you in our Run Club.

May 11, Compost & Seedling Giveaway. Stop by the Public Works Corp Yard in San Mateo and mingle with The Master Gardeners of San Mateo and San Francisco County and learn more about home composting.

May 11, Almost Mother’s Day Kids Concert. Families will enjoy a kids concert with Andy Z and the Andyland Band, an inflatable playland, and can also create a Mother’s Day Gift in the craft area in Redwood City.

May 11, Caltrain Electric Train Tour & 160th Anniversary Celebration. Be among the first to board Caltrain’s new, modern electric trains as they unveil the future of their service in San Carlos. Explore the spacious interiors, learn about the exciting new features, and get a glimpse of what Caltrain will be like in 2024.

May 12, Floral Arranging For Mom Art Class. Join Classpop! In San Mateo for “Floral Arranging For Mom” with Instructor Liza and learn how to craft amazing food.

May 12, Melodies for Mom. Join Sound Union members and friends for a wonderful afternoon of songs to celebrate Mother’s Day at the Sound Union Loft in Redwood City.

May 16, Bay Area Bike to Work Day. Bay Area Bike to Work Day is on Thursday, May 16th to celebrate bicycling and to get your 2024 commemorative bag! Everyone on two wheels is welcome. Show us how you roll by tagging @BayMeadowsLife throughout the month of May! We want to see your errands, commutes and where you’re riding from Bay Meadows. Find an energizer station on the map here.

May 18,  Ukulele Jam led by Charlie Chin on downtown San Mateo’s B Street from 1-3pm. 🎶 Got a uke? Bring it on! 🌟 Strum, sing, and join the fun at this gathering led by San Mateo’s own musical maestro, Charlie Chin. All skill levels are welcome! Don’t worry if you don’t have one – a limited stash to borrow will be on hand, courtesy of the San Mateo Public Library. Stick around for a chance to win a pineapple or even score a brand-new ukulele! 🍍

May 18, Annual E-waste & Shredding Event. San Mateo residents with provide proof of residency can bring paper documents and confidential materials for safe and secure shredding done onsite at Beresford Park.

May 18, Seasonal Wreath Making Workshop. Have a relaxing time while creating a beautiful decorative wreath in this San Mateo class.

May 18, Soul Stroll. Enjoy a day filled with family fun and community feels in San Mateo. Walk, run, or bike while exploring our vibrant health-centered marketplace featuring nonprofits, small businesses, and more.

May 19, Chocolate Swiss Roll or Neapolitan Style Pizza. Whether you want to learn to whip up something sweet or savory, Baking Arts in San Mateo has you covered.

May 20, In A Landscape: Filoli Historic House & Garden. This outdoor concert series where America’s most stunning landscapes replace the traditional concert hall in Woodside.

May 22, Grapes and Giggles May Comedy Show. See comedians featured on late-night TV, Comedy Central, SF Sketchfest, Bay Area Festivals and more at the Domenico Winery in San Carlos.

May 25, Coyote Point Recreation Area. Enjoy a leisurely stroll around Coyote Point Park in San Mateo. With its large variety of habitats, you should see several species.

May 25, Free Art Project at Magical Bridge Playground. Projects will take place in the Kindness Corner to the right of the main entrance and will be available on a first come first served basis in Redwood City.

May 26, Glider Discovery Day. Discover the world of flight in a special outdoor family event at the Hiller Aviation Museum in San Carlos.

May 31, Music on the Square. Enjoy music for thirteen weeks throughout the summer on Friday evenings in Redwood City through August 30. With top-quality local and national musical performers — from rock and reggae, to Americana and much more— music fans of all ages will be thrilled to discover and enjoy the most popular summer concert series on the Peninsula.

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.