Bay Meadows

Get jammin’ in June with a full agenda! Celebrate the new summer season with giggles, music in the park, outdoor movies, airshows, hikes, and much, much more at Bay Meadows and beyond. 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.

June 3, 11, 17 + 25, Stand Up Comedy in Downtown San Mateo at Bobabia. Each week we bring the best comedians in the Bay Area and beyond right to San Mateo.

June 4 – 12, San Mateo County Fair returns with live music, fair foods, farm animals, carnival rides and more! View the music line-up and get tickets.

June 4, Bubbles & Rainbows. Science and craft stations at CuriOdyssey, including: bubble art gift wrap. how to make your own rainbow. make art with bubbles + more.

June 4, Pub In the Park. Bring lawn chairs and blankets for a picnic style afternoon, complete with FREE live music and lawn games such as croquet, cornhole (bean bag toss), and more in Redwood City.

June 5, Spring Dance Show in San Mateo. Pack a blanket, find a spot on the grass, and bring along your family and friends to enjoy the show with dance styles from Creative and Modern to Jazz, Hip Hop, Tap and Ballet.

June 5, All About Bees. Come to the San Mateo Arboretum Society Victorian Garden and meet at the Fairy Garden to explore the world of bees. The kids will hear about some amazing bee houses and discover the plants that bees like.

June 5, Sunday Funday: Sports Day. Shoot hoops, compete in rope and ladder drills, and play mini golf at the Hillsdale Shopping Center. Kids of all ages are welcomed.

June 11, Biggest Little Air Show. Join the festivities as the Biggest Little Air Show presented by PEAXY matches a thrilling aerobatic performance at the Hiller Aviation Museum in San Carlos.

June 11, Bark n’ Brewfest. Bring your pooch to West Washington Park in Burlingame for a fun filled afternoon with local craft breweries, cider makers, and a few artisan wineries will be pouring samples.

June 11, San Mateo County Pride Celebration ~ Still Here, Still Proud. This year Pride Celebration (in-person) will be on Saturday, June 11th at San Mateo Central Park from 11am-5pm. We will have live entertainment, live DJ, resource and vendor booths, family friendly and more. FREE attendance and Sober Event.

June 12, Sunday Funday: Art Day. Draw with markers, & crayons in Macy’s Center Court at the Hillsdale Shopping Center. Kids of all ages are welcomed.

June 15, Grapes & Giggles Comedy Show. Stand-up comedy at the iconic Domenico winery in San Carlos. You no longer have to travel to Napa or San Francisco for an amazing experience!

June 17, Pride Night at Devil’s Canyon! Enjoy live entertainment and music, support delicious Bay Area food trucks and refresh yourself with pitchers of crisp, cold craft beers in San Carlos.

June 18, San Mateo Team: June Community Ride. Silicon Valley Bicycle Coalition – San Mateo will lead a free community ride from downtown San Mateo to Equator Coffee & Tea near Coyote Point.

June 18, Hard Hat Happy Hour with CycleBar San Mateo. Get a tour of CycleBar San Mateo coming this Summer! Afterwards, head over to Refuge to grab a drink or a bite to eat with the Cyclebar team.

June 19, Hike at Edgewood Park and Natural Preserve. Join a Friends of Edgewood docent for a FREE kid-friendly hike at Edgewood Park and Natural Preserve in Redwood City.

June 23, Central Park Music Series. Head to Central Park in San Mateo on Thursdays from 6:00-8:00pm this summer.

June 25, Classical on the Square – Redwood City. This season, conductor Eric K will lead members of Redwood Symphony in a thrilling concert featuring the works of John Williams.

June 26, Sunday Funday: Chess & Game Day. Learn to play chess, one of the world’s most popular board games, and other strategic games at the Hillsdale Shopping Center.

June 30, Central Park Music Series. Head to Central Park in San Mateo on Thursdays from 6:00-8:00pm this summer.

Wednesdays in June, Music in the Park. Redwood City is offering free music for TEN full weeks throughout the summer! June 22 through August 24, 2022.

Fridays in June, Music on the Square. Redwood City is bringing you FREE music for FOURTEEN weeks throughout the summer on Friday evenings from 6 to 8 pm. June 3 through September 2, 2022.

June 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.

Looking for a great place to ride? Bay Meadows and the surrounding San Mateo area are bike friendly and offer many different paths to ride and sights to see including the Bay Trail directly from our MidUrban neighborhood. Plus, Bay Meadows has a convenient bike map that you can download here, so you can decide exactly where to ride. Some resident favorites include Coyote Point Park, and here’s a handy list of 10 sites within a six-mile bike ride. Be sure to join the Bay Meadows email list to stay on top of fun dates, such as Bike to Work Day!