Bay Meadows

Soak up the last bit of summer this September! We’ve rounded up an agenda packed with fun including live music, movies, festivals, comedy, kids’ activities, and much, much more at Bay Meadows and beyond. Map out your month! When you live just steps from Caltrain it’s easy to get from here to ‘there’ car-free! Get the Hillsdale Caltrain schedule here.

September 1, Music on the Square – Pride & Joy. Pride & Joy SF has remained the most popular party band on the Bay Area music scene. Head to Redwood City to enjoy the music!

September 1, First Friday Nights. Swing into the weekend with music, science, animals and fun! On the first Friday of every month parents and kids celebrate together at CuriOdyssey in San Mateo.

September 1, Free First Friday. Admission is free at the SMC History Museum in Redwood City. Online, preschoolers can listen to a story and make a craft.

September 1, 8, 15, 22, 29, Rock the Block Concert. Rock out for FREE and join the jam at our “Rock the Block” Concert Series every Friday evening in September from 6-8pm. Relax, dine and dance under the stars to a different sound each week. North Block Plaza at the Hillsdale Shopping Center in San Mateo.

September 2, Classic and Custom Car Show. Classic, custom & vintage cars will displayed throughout the day in San Mateo along with music, local vendors, food, beverages , and more.

September 3, Moss Wall Workshop. Bring nature into your spaces with this relaxing and fun moss wall art workshop in San Mateo.

September 7 + 14, September Nights on B Street. Grab take-out from a local restaurant and join outdoor pop-up dining in Downtown San Mateo on B Street in the pedestrian malls between First and Third Avenues.

September 7, 14 + 21, Summer Nights. Wander and wonder on Thursday nights at Filoli in Woodside.

September 8, 15, 22 + 29, Movies in the Park. Watch a movie under the stars in San Mateo. Concession sales and activities by Mobile Recreation begin at 6:00pm. Movies start at dusk between 7:30-7:45pm.

September 9, Pub In the Park. Imagine a leisurely summer afternoon in Redwood City lounging in a park, while listening to bluegrass music, sipping delicious local brews and enjoying lawn games.

September 9, 44th Annual Palestine Cultural Festival. Enjoy a day filled with vibrant celebrations of Palestinian culture in Foster City.

September 9, Open Cockpits. The doors and canopies of many aircraft at the Hiller Museum in San Carlos’ collection swing open to allow visitors a special chance to sit inside and explore.

September 10, Eco-Friendly Weed Management in San Mateo. Learn how to identify weeds and deal with them in a safe and eco-friendly way using herbicides only as a last resort.

September 12, lululemon Burlingame Run Club. Join the run, walk, jog and connect with the Burlingame store team and community.

September 16, Get to the Bay Meadows beer garden and raise a stein! Oktoberfest kicks off with beer, brats and live oompah music from Blow Musik from 3-6pm at Fieldwork Brewing Company San Mateo. Prost! This Bavarian tradition, held from 9/16-10/3, is all about fun, beer, music…beer… and you can enjoy it in your front yard at Bay Meadows!

September 16, Grapes & Giggles Comedy Show. You no longer have to travel to San Jose or San Francisco for comedy – head to the iconic Domenico Winery in San Carlos.

September 17, Fiestas Patrias. Courthouse Square in Redwood City will be transformed into a festive, beautiful, and fun setting in celebration of this important patriotic holiday in the Mexican culture.

September 20, Bird Walk-Coyote Point County Park. Join a leisurely stroll around Coyote Point Park in San Mateo looking at the abundant shorebirds and hopefully, some fall migrants.

September 22, Movies in the Parks. Head to Alexander Park in Belmont for an evening of movies under the stars.

September 23-30, Safety & Wellness Days. San Mateo Police Activities League returns to the Hillsdale Shopping Center in San Matero with two weekends of activities promoting wellness and sportsmanship.

September 24, Kids Carnival. Aircraft checkouts, cockpit exploration, glider and helicopter construction and more are just some of the activities available at the Hiller Aviation Museum in San Carlos.

September 30, Chocolate Tempering Essentials. This class in San Mateo covers all the fundamental science and technique of tempering chocolate and making a variety of dipped and molded candies.

September 30, Let’s squeeze the last of September at the best outdoor block party on the Peninsula where there is fun for all ages in the heart of downtown San Mateo. Enjoy a wide variety of music, entertainment, local arts, gastronomical delights, and family-friendly activities all day as you stroll down B Street on September 30 at the San Mateo Fall Fest. Craft beer and cider as well as a selection of local wines will be available for purchase to quench your thirst.

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.

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.