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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.

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.

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 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 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.

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.

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.