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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, 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 storytime, and adults can join a docent-led tour of the museum.

September 4, 11, 18 + 25, Movies in the Park. Enjoy FREE movie nights under the stars at Central Park 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 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.