Bay Meadows

Enjoy the end of summertime and get ready to usher in fall with a full month of activities in the Bay Meadows neighborhood and beyond. It’s time to Rock the Block at Hillsdale and spend September Nights on B Street. We’ve rounded up an agenda full of festivals, bike rides, movies, music, and even specialty events for you and your pup. 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.

September 4, 7, 11, 14, 18, 21, 25, 28, Bay Meadows Run Club with Basecamp San Mateo. Join this free fun run Wednesday evenings at 5:30pm 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!

September 7, 14, 21, 28, 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 everything you need, from the freshest summer fruits and vegetables like berries, corn, tomatoes, peppers, peaches, and summer squash to delightful extras like cut flowers, local honey, jams and sauces, locally-made olive oil, and chocolates. Also find fresh eggs, grass-fed beef, cheeses, and seafood. Seasonal Highlight: Beans, Fresh. Watch for fall favorites to start rolling in!

September 1, Ballet Barre Classes. Join Motion Arts Center for Ballet Barre Classes in San Mateo and get ready to tone your body have fun dancing!

September 6, Movies in the Park. Enjoy a night under the stars and watch a movie outdoors at Central Park in San Mateo. Movies start at dusk between 7:30-7:45pm. Bring your own blanket and chair.

September 6, 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.

September 6, Rock The Block: Twist on Taylor. Performing live at Rock the Block Series at the Hillsdale Shopping Center in San Mateo.

September 7, Family Fun Ride and Bike Rodeo. Invite your family and friends and enjoy a morning of bicycle-related activities in San Mateo. Don’t forget to bring your bike or scooter and a helmet.

September 7, Hops and Props. What could be better than microbrew beer, live music and cool airplanes under the warm September sky? The Hiller Aviation Museum in San Carlos presents Hops & Props Beer Fest.

September 7, Pub in the Park. Enjoy a stocked British-style pub in Redwood City with quality beers and ciders on tap.

September 8, Geraniaceae – The Exciting World Of Geraniums And Pelargoniums. Enjoy a seminar from a Master Gardener at the San Mateo Arboretum Society in San Mateo.

September 12, September Nights on B Street. Family fun returns to B Street! Grab take-out from a local restaurant and enjoy outdoor dining in Downtown San Mateo in the pedestrian mall between First and Second Avenues. The street will be transformed into an outdoor dining pavilion with communal tables and chairs. Live music by Pure Ecstasy.

September 13, Rock The Block: Dan Ashley. Performing live at Rock the Block Series at the Hillsdale Shopping Center in San Mateo.

September 13, Movies in the Park. Enjoy a night under the stars and watch a movie outdoors at Dr. MLK Jr. Park in San Mateo. Movies start at dusk between 7:30-7:45pm. Bring your own blanket and chair.

September 14, Kids’ Carnival. Join the excitement with special activities just for kids at the Hiller in San Carlos.

September 14, Autumn Moon Festival. Enjoy a One-mile Kaiser Permanente Generation Walk for Wellness in San Mateo Central Park to celebrate the Autumn Moon Festival and support healthy living for all generations. Bring your grandparents, parents, children, friends, co-workers, and caregivers.

September 15, Bark in the Park. Bring your dog down to Central Park in San Mateo and enjoy a paw-some pup parade, contests, games and more.

September 19, September Nights on B Street. Family fun returns to B Street! Grab take-out from a local restaurant and enjoy outdoor dining in Downtown San Mateo in the pedestrian mall between First and Second Avenues. The street will be transformed into an outdoor dining pavilion with communal tables and chairs. Live music by Mercy and The Heartbeats.

September 20, Movies in the Park. Enjoy a night under the stars and watch a movie outdoors at Los Prados Park in San Mateo. Movies start at dusk between 7:30-7:45pm. Bring your own blanket and chair.

September 20, Rock The Block: Fire Peach. Performing live at Rock the Block Series at the Hillsdale Shopping Center in San Mateo.

September 20 + October 4, Movies in the Parks – Alexander Park. Enjoy annual Movies in the Parks showings in Belmont. All movies will begin at sundown. Bring your own blankets and pick up some take-out food from the nearby restaurants. Come before the movie to play games.

September 20-22 and 24-29, Oktoberfest. Dive into the heart of the season with Redwood City’s most anticipated fall event– Oktoberfest Downtown Redwood City! Immerse yourself in the exciting atmosphere of a classic Oktoberfest, where the spirit of traditional German revelry comes alive.

September 21, San Mateo Bay Trail Ride. Move San Mateo & San Mateo’s Age-Friendly Coalition are joining to organize a group bicycle ride along San Mateo’s Bayshore trail.

September 21, Rancho Day Fiesta. The San Mateo County Historical Association’s docents at the Sánchez Adobe present their annual Rancho Day Fiesta in Pacifica. A living history event, visitors will be invited to make adobe bricks, stamp leather, dip candles, make corn husk dolls, churn butter, and participate in other rancho-era activities, including learning how to dance as the early Californios did.

September 22, Yoga With Jen. Stretch your hamstrings, open the hips, release the back and relax the mind in this all levels yoga class at the Hillsdale Shopping Center in San Mateo.

September 27, Movies in the Park. Enjoy a night under the stars and watch a movie outdoors at Beresford Park in San Mateo. Movies start at dusk between 7:30-7:45pm. Bring your own blanket and chair.

September 28, September Arts & Culture Fest. This day-long event features local musicians, entertainment and cultural performances, artists and craft-makers, cuisine from around the world, wine and beer, and family-friendly activities in the heart of Downtown San Mateo. The event is free and open to the public.

September 29, September Market to Market! Belmont to San Carlos Ride. Start your Sunday with not one, but two great local Farmer’s Markets. Grab some produce, have some prepared goodies, and get a fun ride between the two markets.

September 29, Croissant and Pain Au Chocolat. Learn how to prepare melt in the mouth all butter croissants and pain au chocolat in the classic French method at Baking Arts in San Mateo.

September/October 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.

Rock the Dock Concert Series. Lounge on the Redwood City waterfront and enjoy live music, dancing, food and fun! Rock the Dock concerts run every Saturday through November 2024.

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.