Bay Meadows

Get ready for an exciting month in the Bay Meadows neighborhood and beyond! With a diverse range of activities, you’ll find something for everyone. 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 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 welcome. 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.

Tuesday 25th Avenue San Mateo Farmers’ Market. Back through October 21 on Tuesdays from 3pm to 7 pm, this farmers 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.

Sunday Downtown San Mateo Farmers Market. West Coast Farmer’s market is kicking off a new location at 222 East 4th Avenue Sundays from 9am to 2pm in Downtown San Mateo. The new farmer’s market will have a curated selection of fresh fruits, veggies, and a couple of tasty food trucks to fuel your morning stroll.

Saturday 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.

Wednesdays + Thursdays September 3 thru 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.

Fridays, September 5, 12, 19 and 26, Moves in the Park. Enjoy a night under the stars and watch a movie outdoors in San Mateo! Movies start at dusk between 7:30-7:45pm. Bring your own blanket and chair. Admission is free. Sept 19 INSIDE OUT 2 plays at Bay Meadows Park!

Fridays September 5, 12, 19 and 26, Hillsdale Shopping Center’s Rock the Block Concert Series. Walk on over to Hillsdale from Bay Meadows every Friday evening in September for a high energy outdoor concert series featuring four incredible musical acts, each bringing their unique sound to the North Block Stage.

September 6, San Mateo Firefighters Association’s Chili Cook Off. The SMC Firefighters Annual Chili Cook-Off is back at Central Park, Downtown San Mateo with live music, craft beer a kids jump house and more.

September 6, Pub in the Park. Pub in the Park in Redwood City is transforming Red Morton Park into the perfect hangout spot each month this summer. Relax in a cozy, inflatable British-style pub, sip a refreshing pint from local microbreweries, or enjoy a variety of delicious ciders and seltzers on tap.

September 6, Hops & Props. What could be better than microbrew beer, live music, food and cool airplanes under the warm September sky? The Hiller Aviation Museum in San Carlos presents Hops & Props Beer Fest.

September 7, Begonias. There is a begonia to fit almost any partially shaded spot in your home or garden. Learn all about begonias in this San Mateo class.

September 12, Movies in the Park. Movies at Alexander Park in Belmont begin at sundown. Bring blankets, camping chairs, and your favorite movie snack. Come early to get takeout from local restaurants.

September 19, Moves in the Park at Bay Meadows Park – INSIDE OUT 2. Enjoy a night under the stars and watch Inside Out 2 outdoors at Bay Meadows Park in San Mateo! Movies start at dusk between 7:30-7:45pm. Bring your own blanket and chair. Admission is free.

September 20, Exotic Car Show. Experience a world where speed, style, and precision meet. The Hiller Aviation Museum in San Carlos is hosting an Exotic Car Show featuring breathtaking rides from Ferrari, Lamborghini, McLaren, Porsche, and more — plus a look at the sleek Cirrus Aircraft. 

September 21, The annual Oktoberfest celebration kicks off at Fieldwork Brewing San Mateo with all the essentials: limited-edition steins, German-inspired bites, live music, fun & games, and many glorious pours of Fest & Last, the house Oktoberfest Lager brewed for peak fest season vibes.

September 21, 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.

September 25, HarringTunes. Enjoy a casual afternoon of music and chess at Frank D. Harrington Park in San Carlos. Both permanent chess boards installed by the Parks and Recreation Foundation of San Carlos will be stocked with pieces and ready to play, while you listen to live music played by local performers.

September 26, The Art and Science of Sourdough. This is a fully hands on bread making class for sourdough at Baking Arts in San Mateo. Learn the essentials of creating and maintaining natural starters, preparing sourdough breads and techniques for pulling, shaping, forming, scoring and baking.

September 27, Belmont Water Dog Run. The annual 5k, 10k, 1 mi kids, and 1 mi Fido runs have a bit of something for everyone. All events start at Twin Pines Park. The 5k run is an out-and-back with the turnaround point a bit past Carlmont Shopping Center. The 10k shares the same outbound and inbound portions as the 5k but adds a challenging and scenic trail portion up Lake Trail in Belmont Waterdog Park.

September 28, September Arts and Culture Fest. Enjoy 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.

Thru November, Rock the Dock Concert Series in Redwood City. Enjoy live music, dancing, food and fun on the waterfront. Concert-goers should bring lawn chairs, blankets, jackets and refreshments. On-site food vendors will also be available.

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 timeslot. 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.

 

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.