Bay Meadows

Get ready for an exciting month in the Bay Meadows neighborhood and beyond! Go ‘Off the Grid’, laugh out loud at a local comedy show, shop the 25th Avenue Farmers’ Market, enjoy craft beer with dad in Bay Meadows Fieldwork Beer Garden, HEAD WEST in downtown San Mateo, and hit the San Mateo Pride Parade and Celebration in Central Park. Explore our curated agenda, explore, and plan a month bursting with fun and adventure!

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: Arugula.

June – August, Central Park Music Series. 2025 concerts to be announced. Central Park Music Series is a signature summer event that brings you free live music every Thursday evening. Music lovers of all ages gather for an evening of music, dancing, food, and fun!

June 1, Karaoke World Championships. Are you the next Karaoke World Champion for 2025? Audition at McGoverns in San Mateo and share your voice with the ranks of some of the most talented singers from around the nation & world and find out how far your voice might take you this year!

June 1, Summer Care for Your Roses. This San Mateo class will teach you how to care for your roses in the summer months to maximize repeat and profuse blooming.

June 1-8, 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.

June 3, 10, 17, 24 25th Avenue San Mateo Farmers’ Market – Tuesdays 3 to 7 pm. Back through October 21st 2025, the 25th Avenue San Mateo 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.

June 4, 11, 18, 25 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.

June 5-August 28, Movies on the Square. Every Thursday evening for twelve weeks Courthouse Square in Redwood City transforms into a magical open-air theater with free double features for all ages.

June 6, First Friday Nights. Swing into the weekend with live music, a food truck, animals, and fun at CuriOdyssey in San Mateo.

June 6, 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.

June 7, Cinema & Chill (at Chill Spot Rendezvous). Hangout and enjoy family friendly movies- free every Saturday in San Mateo. Bring yourself and/or your family for movies throughout the day and enjoy laughter, adventure, and excitement as they showcase fun and meaningful films.

June 8, French Macarons. This intimate, 4-person class in San Mateo teaches students how to create macarons from start to finish. Short on ingredients and long on technique, these addictive little treats, crunchy and chewy at the same time, are simply irresistible.

June 11–September 18, Summer Nights at Fioli. Every Wednesday and Thursday evening this summer, experience Filoli in Woodside like never before with exclusive after-hours access. Stroll through the Garden, enjoy live acoustic music, savor local food trucks, or hike the Natural Lands at twilight.

June 13, Laugh Out Loud Comedy Night at Pinstripes Hillsdale in San Mateo. Sip on bold cocktails and share chef-crafted bites while the hilarious comics turn the night into something worth talking about.

June 13-15, Pride Month in Woodside. Celebrate the LGBTQ+ community with a weekend of performances and experiences. Filoli bursts into rainbow color with festive decor, artwork, and live performances.

June 14, San Mateo Pride Parade and Celebration. Enjoy DJ music, food trucks and join neighbors to come together as a community in support of inclusion and wellness for LGBTQIA+ folks and allies at the 13th Annual San Mateo County Pride Parade and Celebration in Central Park on Saturday, June 14. The parade runs 10:30 to 11:30am with a celebration in Central Park from 11am to 5pm. Free and open to all, including pets!

June 14, Biggest Little Air Show at the Hiller in San Carlos. San Carlos Airport will close to regular traffic from to allow realistic electric and gas-powered model aircraft to roll down the runway and into the sky to take their part in a unique aerial extravaganza including aerobatic helicopters, drones, quadrotors and more!

June 14, Summer Bar Crawl Series. Every restaurant at Hillsdale in San Mateo will have a specialty drink, starter and/or specials during their time frame. Purchase what you’d like with your friends. Check in at Pinstripes between 5:30-6pm to receive a card and stamp it along participating bars. Gather all stamps to be entered into a raffle.

June 15-July 13, Belmont Summer Concert Series. Join the Belmont Park Boosters for their annual Summer Concert Series in Twin Pines Meadow. Concerts are held every Sunday from 1-4pm. Open lawn seating. Light concessions will be for sale.

June 15, Father’s Day in the Beer Garden. Dad’s love beer and the outdoors! Combine the two and bring dad to Bay Meadows for some family-friendly fun at Fieldwork Brewing Beer Garden. Open Sunday 11am to 9pm.

June 15, 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!

June 15, 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.

June 15, Father’s Day Brunch at Pinstripes in San Mateo. Offering brunch along with additional proteins such as burger, brats, and chicken for all the hungry fathers.

June 18-August 20, Music in the Park. Ten weeks of free live performances at Stafford Park every Wednesday! Enjoy classic park fare—hamburgers, hot dogs, chips, and drinks in Redwood City.

June 28, Flying Gatsby Ball. Step back in time and celebrate the glitz and glamour of the Roaring 20s at the Flying Gatsby Ball at the Hiller in San Carlos.

Thru August 29, Music on the Square. From rock, reggae, and funk to Latin, soul, and everything in between, this fourteen-week series delivers high-energy performances that keep Courthouse Square in Redwood City rocking and features top-tier talent from across the Bay and beyond. Grab a bite from nearby restaurants, bring a lawn chair or blanket, and let the music move you—it’s the Peninsula’s favorite way to spend a Friday evening.

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.

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! 

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.

When you live just steps from Caltrain it’s easy to get from here to ‘there’ car-free! Get the Hillsdale Caltrain schedule here.

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.