Bay Meadows September Agenda

September brings a fresh energy to the Peninsula, with the last days of summer blending into the first signs of fall. From outdoor movies and live music to farmers markets, community festivals, creative workshops, and seasonal celebrations, there are plenty of reasons to get out and explore close to home.

Spend an evening under the stars, shop ceramics at Art in the Meadows, stroll Downtown San Mateo for local art and entertainment, celebrate Oktoberfest in Redwood City, or enjoy a weekend hike through Belmont’s open spaces. With family-friendly activities, outdoor gatherings, and local favorites happening throughout the month, September is the perfect time to enjoy the community, culture, and easygoing Peninsula lifestyle surrounding Bay Meadows.

It’s transit month, and we’re celebrating at Bay Meadows Transit Oriented Village! When you live just steps from Caltrain, getting from here to there is easy and car-free. Grab the Hillsdale Caltrain schedule and dive into our monthly event roundup to discover all the ways to celebrate, create, explore, and connect throughout the month ahead.

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.

Sunday Downtown San Mateo Farmers Market. West Coast Farmer’s market runs year-round at 222 East 4th Avenue Sundays from 9am to 2pm in Downtown San Mateo. The farmer’s market has a curated selection of fresh fruits, veggies, and a couple of tasty food trucks to fuel your morning stroll.

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.

The 25th Avenue in San Mateo Farmers’ Market. May through October 20 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.

Thru September 3, Summer Nights. Chase the sunset at Filoli. Summer Nights brings a softer, more laid-back vibe than Summer Stage. Think of it as the more chill little brother. Held every Wednesday and Thursday, it is all about golden-hour garden strolls, drinks, bites, and live acoustic music in a relaxed midweek atmosphere.

September 3, Movies on the Square. Expect an energetic, captivating ambiance, and arrive early to claim your space or spread a blanket, then enjoy tasty take-out from nearby restaurants in Redwood City.

September 4, 11, 18 + 25, Movies in the Park. Enjoy FREE movie nights in the park under the stars in San Mateo. Every Friday in September. Bring your own blanket and chair. Mobile Rec games and crafts start at 6 p.m. Movies start at dusk, around 7:30 p.m.

September 4, 11, 18 + 25, Rock the Block. Rock into September with Hillsdale’s Rock The Block Concert Series! Every Friday evening in September from 6–8 PM for free live music, great dining, and unforgettable summer nights in the outdoor North Block Plaza.

September 4, First Friday Nights. On the first Friday of every month, from 5 PM until 8 PM, parents and kids celebrate together at CuriOdyssey in San Mateo. Dance to some of your favorite hits, while enjoying animal presentations and science activities.

September 4, Music on the Square. Grab food from acclaimed nearby restaurants, bring a lawn chair or blanket, and enjoy the show; it’s the Peninsula’s go-to Friday night tradition in Redwood City.

September 4, San Mateo County History Museum FREE First Fridays. Visit the SMCHM every Friday for free First Friday events, where children enjoy special programs including crafts and story time, and adults can join a docent-led tour of the museum.

September 6, Paint-A-Plane. Join the excitement with special activities just for kids! Paint the Cessna Cardinal, check out in an airplane or helicopter, and more at the Hiller in San Carlos.

September 10 + 17, September Nights on B Street. Enjoy free music and entertainment for the whole family in San Mateo. Join the fun between 1st and 3rd avenues from 6–8pm.

September 12, Art in the Meadows. On Saturday, September 12 from 11 am to 4 pm, Clayroom San Mateo is hosting Art in the Meadows, a late Summer Sale + Art Market in collaboration with Caltrain, inviting the community to shop local handmade ceramics and art.

September 12, Hops and Props. What could be better than microbrew beer, live music and cool airplanes under the warm September sky? The Hiller Aviation Museum presents Hops & Props Beer Fest in San Carlos.

September 13, Brunch & Burn. Start your day with an energizing outdoor yoga session at the Hillsdale Shopping Center in San Mateo, followed by a refreshing mimosa and a delicious brunch at Pinstripes. The yoga class will take place in the North Block Plaza, with brunch hosted inside Pinstripes immediately after.

September 17, Hiptwist Fitness San Mateo Grand Opening. Reserve your spot! Join Hiptwist Fitness from 4-7PM to celebrate the opening with Pilates, a ribbon cutting, bites, drinks and community at 740 Polhemus Rd in San Mateo.

September 18 + 25, Movies in the Park. Lights! Camera! Action! Head to Belmont for Movies in the Park. Movies begin at sundown. Come early to save your spot with blankets or camping chairs.

September 18-27, Oktoberfest Downtown Redwood City. Experience traditional cuisine, lively entertainment, and a festive atmosphere as Downtown Redwood City celebrates one of fall’s favorite traditions.

September 19, HEAD WEST Marketplace. Spend the day exploring Downtown San Mateo’s B Street during the HEAD WEST Marketplace, where you can shop handcrafted goods from local makers and artists while enjoying the neighborhood’s vibrant retail shops and dining scene.

September 23, Community Hike. Take a hike in Belmont’s beautiful open spaces! Hikes will be led by recreation staff and they will provide brochures on Belmont trails and wildflowers.

September 25, Royal Icing Cookie Decorating. This San Mateo class covers all the necessary fundamentals you will need to recreate the cookies you have seen in magazines and social media. Halloween and winter theme.

September 26, Belmont Water Dog Run 2026. The annual Belmont Water Dog Run returns on September 26. The 5k, 10k, 1 mi kids, and 1 mi Fido runs have a bit of something for everyone.

September 26, September Arts & Culture Fest. Head to the heart of Downtown San Mateo for a fun day-long celebration of art, music, dance, poetry, food, and culture. From live bands and dazzling cultural performances to interactive kids’ activities, LIVE mural painting competitions, artists selling original handcrafted artworks, and poetry open mic, the September Arts & Culture Fest has something for everyone.

Sep-Oct 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.

Discount Tuesday (at Cinemark Century San Mateo 12). There’s never been a better time to turn up on a weekday, because every Tuesday at Cinemark is Discount Tuesday—cheap movie tickets are always within reach.

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!

Bicycle Sundays. From 9am – 3pm, 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 including jogging, bicycling, hiking, roller-skating, and walking. Cañada Road between Edgewood Road to the Filoli entrance will remain open to vehicles. 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.

Art, Community & Caltrain: Clayroom San Mateo Brings Transit Month to Bay Meadows

Creativity is getting a late-summer spotlight at Bay Meadows. On Saturday, September 12 from 11 am to 4 pm, Clayroom San Mateo is hosting Art in the Meadows, a late Summer Sale + Art Market in collaboration with Caltrain, inviting the community to shop local handmade ceramics and art. The event takes place in Town Square at 3050 S Delaware St., Suite 100, just steps from Hillsdale Caltrain, making it an easy destination for Bay Meadows residents, employees, and art lovers across the San Francisco Peninsula. As part of Transit Month, visitors are encouraged to hop on Caltrain, skip the parking search, and arrive ready to discover something handmade.

Art in the Meadows is a special opportunity for our broader community to highlight local talent while showcasing artisan products, celebrating the connection between creativity, small business, public transportation, and community.

Having a creative studio like Clayroom right in the neighborhood adds another dimension to life at Bay Meadows. For residents and employees, it’s easy to step away from the workday and spend an hour shaping clay, learning a new skill, or meeting up with friends for a class. Creative activities can provide a welcome break from daily routines, helping encourage mindfulness, stress relief, and a healthier work-life balance. And because Clayroom is a community-oriented studio, the experience goes beyond the finished piece—you can meet fellow makers, build friendships, and become part of a growing local creative community without having to travel across the Bay.

It’s all part of what makes Bay Meadows a uniquely connected transit oriented, mid-urban village. With Hillsdale Caltrain nearby, residents and workers can easily arrive by rail, while the neighborhood’s walkable streets, parks, trails, Town Square, and collection of local retailers make it simple to continue the day without getting back in the car.

Mark September 12 on your calendar, hop off at Hillsdale, and make your way to Clayroom San Mateo for an afternoon of art, shopping, creativity, and community. It’s another reminder that when you live and work at Bay Meadows, inspiration—and connection—can be right outside your door.

Bay Meadows August Agenda

August is your last chance to soak in the best of Peninsula summer before the season winds down. Camp out, say “Hello Kitty”, HEAD WEST, hit Hillsdale for outdoor yoga, and get ready for Coyote Point Summerfest. From outdoor concerts and neighborhood festivals to family campouts, artisan markets, and scenic adventures, the month is filled with opportunities to get outside, connect with the community, and create lasting memories close to home.

Whether you’re spending an evening enjoying live music in the park, exploring local makers and restaurants, hiking through Filoli’s natural landscapes, or discovering hands-on experiences for all ages, there’s something happening nearly every day. Before fall arrives, make the most of the warm evenings, vibrant community events, and unforgettable summer traditions waiting just minutes from Bay Meadows.

When you live just steps from Caltrain, getting from here to there is easy and car-free. Grab the Hillsdale Caltrain schedule and dive into our monthly event roundup to discover all the ways to celebrate, create, explore, and connect throughout the month ahead.

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.

August 1 + 29, Pub in the Park. Enjoy a day in Redwood City with music, drinks, and a welcoming community atmosphere in an inflatable British-style pub.

August 2, Paint-A-Plane. Join the excitement with special activities just for kids! Paint the Cessna Cardinal, check out in an airplane or helicopter, and more at the Hiller in San Carlos.

August 4, National Night Out. If you are not going to a registered block party, head to the Martin Luther King Jr Center from 5:30 – 8:00 pm for music, McGruff the Crime Dog, resources, raffles, goodies, and more. Strengthen your community by knowing your neighbors, watching out for each other, and working together for a safe community. This event is open to all residents and blocks in the City of San Mateo.

August 6, Central Park Music Series. Enjoy summer evenings at Central Park in San Mateo featuring live music, local food vendors, family-friendly activities, and plenty of sunshine every Thursday through August.

August 6, Sunset Hikes. Wander through Filoli’s in Woodsides natural lands in search of mushrooms, fungi, lichen, and mosses. Guided by experts, you’ll explore both familiar trails and quieter corners where these treasures await.

August 7, First Friday Nights. On the first Friday of every month, from 5 PM until 8 PM, parents and kids celebrate together at CuriOdyssey in San Mateo. Dance to some of your favorite hits, while enjoying animal presentations and science activities.

August 7, San Mateo County History Museum FREE First Fridays. Visit the SMCHM every Friday for free First Friday events, where children enjoy special programs including crafts and storytime, and adults can join a docent-led tour of the museum.

August 7-8, Family Campout. Pitch a tent and camp under the stars in Burton Park in San Carlos! This is a great way to gather with friends and enjoy a variety of activities, including crafts, field games, s’more roasting, and a movie at dusk.

August 8, Sounds of the Shores. Enjoy live music in the scenic surroundings of Redwood Shores across three Saturdays. Held at Marlin Park.

August 9, Brunch & Burn. Start your day with an energizing outdoor yoga session at the Hillsdale Shopping Center in San Mateo, followed by a refreshing mimosa and a delicious brunch at Pinstripes. The yoga class will take place in the North Block Plaza, with brunch hosted inside Pinstripes immediately after.

August 14 + 21, Music in the Park Concert Series.Spend your summer evenings at Burton Park in San Carlos during the free 2026 Music in the Park Concert Series, where live music, picnic-friendly vibes, and community fun come together every Friday from June through August.

Thru August 14, Summer Concert Series. Spend your Fridays nights from 6-8pm in the Leo Ryan Amphitheater for free live music in Foster City.

August 14-16 Foster City Summer Days 2026 takes over beautiful Leo J. Ryan Park, 650 Shell Boulevard, August 14–16 for a free, family-friendly weekend filled with live music, carnival rides, local vendors, food, and plenty of reasons to get outside.

August 15, Coyote Point Summerfest: A Community Celebration. The annual event features giant kite displays, live cultural performances, kiddie train rides, arts and crafts, community resource booths, and food trucks.

August 15, HEAD WEST Marketplace. Spend the day exploring Downtown San Mateo’s B Street during the HEAD WEST Marketplace, where you can shop handcrafted goods from local makers and artists while enjoying the neighborhood’s vibrant retail shops and dining scene.

Thru August 19, Music in the Park. Spend your summer evenings at Stafford Park in Redwood City with free live music! The 2026 lineup kicks off with the vibrant Brazilian jazz sounds of Masha Campagne, followed by a dynamic blend of funk, soul, Latin rock, and beyond. It’s an ideal setting to socialize with friends and family in a relaxed outdoor atmosphere.

August 22, Hello Kitty Café Truck. North Block Plaza at the roundabout near Cinepolis and Flores at Hillsdale Shopping Center in San Mateo. The truck will feature Hello Kitty merchandise which will be available for purchase to the public.

August 30, Chocolate Babka.This irresistible loaf cake can go from a morning brunch to the perfect way to end an evening meal. Students at Baking Arts in San Mateo will make tender, buttery brioche dough from scratch and our deliciously fudge-y chocolate filling.

Thru September 4, Music on the Square. Downtown Redwood City’s Music on the Square offers something for all ages. Featuring the best of rock, reggae, funk, Latin, and soul on Friday nights. Grab food from acclaimed nearby restaurants, bring a lawn chair or blanket, and enjoy the show; it’s the Peninsula’s go-to Friday night tradition!

June-Aug 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.

One More Reason to Leave the Car Behind: The Free Hillsdale Caltrain Commuter Shuttle

Living or working at Bay Meadows means having more choices for how you get around the Peninsula. Already home to walkable streets, dedicated bike paths, and easy access to Hillsdale Caltrain, the neighborhood is also served by the free Hillsdale Caltrain Commuter (HCC) Shuttle from Commute.org. Whether you’re commuting into San Francisco, heading south to Silicon Valley, or simply making your way home from the office, this complimentary shuttle helps make the journey even easier. It’s just another example of how Bay Meadows was thoughtfully planned to support a connected, transit-oriented lifestyle.

The Hillsdale Caltrain Commuter Shuttle operates Monday through Friday with morning service from 7:00–10:00 a.m. and afternoon service from 3:00–6:30 p.m., arriving approximately every 30–45 minutes. The shuttle is fully wheelchair accessible and equipped with a bike rack, making it easy to combine walking, biking, and rail travel into one seamless commute. Bay Meadows residents can enjoy a quick connection to Hillsdale Caltrain, while employees working throughout Bay Meadows Station—including teams at Roblox, Freshworks, and Upstart—can take advantage of an easy connection between work and local stops.

The Hillsdale Caltrain Commuter Shuttle serves the following stops:

Hillsdale Caltrain Station
Saratoga Drive & Park Place (morning service only)
Saratoga Drive & Yates Way (afternoon service only)
1400 Fashion Island Boulevard
Mariners Island Boulevard & Fashion Island Boulevard
Mariners Island Boulevard & Armada Way
2207 Bridgepointe Parkway

Whether you’re looking to simplify your weekday commute, reduce time behind the wheel, or embrace a more sustainable way to travel, the Hillsdale Caltrain Commuter Shuttle makes getting around San Mateo easier than ever. If you’re considering making Bay Meadows your next home, this is one more reason to explore The Apartment Collection at Bay Meadows.

With five distinctive apartment communities, walkable access to neighborhood shops and restaurants, and convenient transit connections just outside your door, it’s a lifestyle designed to keep you connected to everything the Peninsula has to offer. To view the shuttle route and schedule, visit HERE. For real-time service alerts, text HCCALERTS to (833) 426-6688.

Where Commutes Shrink and Life Expands: Living in Motion at Bay Meadows

Living well starts with location, and Bay Meadows was thoughtfully designed to put everyday life into better balance. Situated along the Hillsdale San Mateo Caltrain line, this transit-oriented neighborhood makes moving up and down the Peninsula refreshingly simple. Caltrain Express Service connects residents to Palo Alto in just 11 minutes, San Francisco in 26 minutes, and San Jose in 33 minutes—transforming what was once a stressful commute into time reclaimed. Less time in traffic means more time to enjoy mornings that move slower, evenings that last longer, and a lifestyle that feels intentionally designed.

Experience Life in Motion at Bay Meadows

Bay Meadows is also uniquely positioned as a place where living close to work isn’t just convenient—it’s energizing. Visionary companies like Roblox, Upstart, and Freshworks already call the neighborhood home, creating a dynamic ecosystem where careers and community coexist. With five thoughtfully designed apartment communities within The Apartment Collection at Bay Meadows, residents have the flexibility to live just steps from where they work—or easily commute elsewhere—without sacrificing comfort, style, or access. It’s a model of modern living that supports productivity while leaving room to breathe.

What truly sets Bay Meadows apart is how seamlessly workday rhythms blend into everyday enjoyment. Coffee breaks happen at Blue Bottle Café. Morning brainstorms unfold over pancakes at The Breakfast Club at Midtown San Mateo. Afternoon team building workshops and post-work creative release at Clayroom San Mateo. Evenings wind down with Wine Down Wednesdays at Bahche Wine Bar or casual meetups in the Fieldwork Brewing San Mateo beer garden. Midday ping pong matches, post-work runs with the Basecamp San Mateo Bay Meadows Run Club, and spontaneous neighborhood gatherings turn ordinary moments into something more social, more active, and more human.

Beyond its vibrant social energy, Bay Meadows offers 18 acres of parks and open space designed to keep life in motion. Pocket parks invite lounging, connecting, and play, while porch swings, bocce courts, and ping pong tables create a true “front yard” feel. Walking and biking trails weave throughout the neighborhood and connect directly to the Bay Trail, making it easy to stay active without ever leaving the community. At Bay Meadows, balance isn’t a buzzword—it’s built into the streets, the green spaces, and the everyday flow of life.