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.

Thank You for Celebrating Resident Appreciation Day with Us!

Community is at the heart of everything we do at The Apartment Collection at Bay Meadows, and on June 25, the Bozzuto leasing team had the pleasure of celebrating the people who make this neighborhood so special during their annual Resident Appreciation Day. From morning mimosas to evening Bingo, the day was filled with opportunities to relax, connect with neighbors, and enjoy everything that makes life at Bay Meadows unique. We want to extend a heartfelt thank you to everyone who joined us and to our incredible neighborhood retail partners who helped make the celebration one to remember.

For Brian, The Apartment Collection at Bay Meadows, Sr. General Manager: Resident Appreciation Day highlighted exactly what makes Bay Meadows feel like home. “RAD Day was a great reflection of the amazing sense of community we have here at Bay Meadows. It was wonderful getting to connect with residents throughout the day and see everyone enjoying the activities, food, and time spent with their neighbors. Seeing residents meet new people, share laughs, and make memories together was truly special. We also loved seeing our four-legged residents join in on the fun—pets are family too! Events like RAD Day highlight what makes Bay Meadows such a vibrant and welcoming place to call home.”

The festivities began in the leasing office, where residents stopped by throughout the day for a complimentary mimosa, sparkling apple cider, and a chance to mingle with neighbors. The fun continued poolside at The Russell, where residents cooled off with floaties, pool games, and plenty of sunshine, while families enjoyed the Resident Fun Zone complete with a bounce house, popcorn, and cotton candy between The Russell and Hawthorne. Throughout the day, our Bay Meadows retail community showed their appreciation in thoughtful ways. The Breakfast Club at Midtown San Mateo served complimentary pancakes and resident discounts, LFBA Studios welcomed residents to a complimentary Lagree class, Basecamp Fitness offered free classes and generous swag bags with two-week memberships for Bingo winners, Clayroom San Mateo invited residents to explore their creative side with discounted pottery classes, and our San Mateo neighbors from Beem Light Sauna introduced residents to complimentary red light therapy sessions in The Russell Clubroom.

The evening wrapped up with a lively Resident Appreciation Social in The Morgan Clubroom, where neighbors gathered around a build-your-own taco bar featuring chicken, beef, fresh toppings, chips and salsa, fruit and vegetable platters, and refreshments before settling in for several spirited rounds of Bingo and prize giveaways. For Leasing Manager Victoria, one moment perfectly captured the spirit of the evening. “One of my favorite moments from RAD Day was Bingo Night. It was so much fun watching residents laugh, cheer each other on, and connect with their neighbors. The sweetest moment was when a resident’s young daughter helped call out the bingo letters and numbers. She took her job so seriously, and it was absolutely adorable. Seeing everyone come together and create those little moments of joy is what made the event so special.”

Namrita reflected on the day’s bigger picture, sharing, “What stood out to me most about RAD Day was the incredible sense of community. It was amazing to see our residents, local vendors, and neighborhood partners all come together to create such a memorable experience. From complimentary treats and fitness classes to red light therapy, an interactive jump house, and a fun pool day, there was truly something for everyone to enjoy. Events like this remind us how fortunate we are to be part of such a vibrant and connected community.”

To everyone who attended, volunteered, partnered with us, or simply stopped by to say hello—thank you for making Resident Appreciation Day such a success. We can’t wait to celebrate with our residents again at our next community event!

Bay Meadows July Agenda

July brings the best of summer to the Peninsula, with outdoor concerts, community celebrations, family-friendly festivals, and unforgettable evenings under the stars. From Fourth of July festivities and live music in local parks to garden strolls at Filoli and hands-on activities for kids, there are countless ways to make the most of the season just minutes from Bay Meadows.

This month’s lineup features beloved traditions like Music on the Square, Music in the Park, and the Central Park Music Series, alongside unique experiences including outdoor yoga and brunch, model train and aviation exhibits, artisan marketplaces, and culinary classes. Whether you’re looking for a relaxing evening of live music, a fun family outing, or a new local adventure, July offers something for every age and interest across San Mateo and the surrounding Peninsula.

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.

July 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.

July 1-25, Camp Pinstripes. Make the most of summer Saturdays at Camp Pinstripes in San Mateo, where kids can enjoy free hands-on activities like tie-dye, friendship bracelets, magic shows, princess visits, and more, plus complimentary brunch every week in June and July.

July 3, 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.

July 4, 4th of July in the Park. Celebrate red, white, and blue with a special concert on Saturday, July 4, 2026 from 11 a.m. – 2 p.m. in Central Park in San Mateo.

July 4, Celebrate July 4th in Redwood City. Enjoy a full day of patriotic fun to celebrate America’s 250th anniversary with family-friendly activities, community traditions, and the exciting return of fireworks.

July 4, Fourth of July Celebration. Foster City’s hosts an annual Fourth of July celebration! Festivities include breakfast, lunch, live entertainment, family games, and bike, family, and dog parade.

July 9-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.

July 10-August 14, Summer Concert Series. Spend your Fridays nights from 6-8pm in the Leo Ryan Amphitheater for free live music in Foster City.

July 10-August 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.

July 11, Pub in the Park. Enjoy a day in Redwood City with music, drinks, and a welcoming community atmosphere in an inflatable British-style pub.

July 11-12, Trains & Planes Eurowest Expo. Come and see both Planes and Trains, in a skillfully crafted display of HO scale model trains featuring the scenery and villages of Europe at the Hiller Aviation Museum in San Carlos.

July 12, 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.

July 18, 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.

July 18, Sounds of the Shores. Enjoy live music in the scenic surroundings of Redwood Shores across three Saturdays. Held at Marlin Park.

July 19, 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.

July 26, Neapolitan Style Pizza. Learn how to make a classic pizza made with hand stretched dough in the Neapolitan style at Baking Arts in San Mateo. Each student will make their own pizza dough from scratch that will be taken home.

All month long, residents can explore everything from outdoor concerts at Central Park, San Mateo and Burton Park to creative workshops, community hikes, Pride celebrations, and pop-up markets throughout San Mateo, San Carlos, Belmont, and beyond. Whether you’re looking for live entertainment, local makers, or family activities, June offers something happening nearly every weekend just minutes from home.

Bay Meadows June Agenda

June in the Bay Meadows area is packed with summer energy, bringing together festivals, live music, cultural celebrations, and hands-on community experiences across San Mateo and the surrounding Peninsula. From family-friendly events at CuriOdyssey and the San Mateo County History Museum to major seasonal highlights like the San Mateo County Fair and the Bayside 101 Music Festival, the month is filled with opportunities to get outside and connect.

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.

The 25th Avenue in San Mateo Farmers’ Market. Back 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.

June 5, First Friday Nights. On the first Friday of every month parents and kids celebrate together at CuriOdyssey in San Mateo. Swing into the weekend with music, food trucks, animals, and fun!

June 5, 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.

June 5-6, Bayside 101 Music Festival. Experience two nights of live music and festival fun at the Bayside 101 Music Festival, taking place during the San Mateo County Fair and included with general admission.

June 5-June 14, San Mateo County Fair. Celebrate summer at the San Mateo County Fair, where carnival rides, live entertainment, concerts, exhibits, fair food, games, and family-friendly fun come together for one of the Peninsula’s favorite annual traditions.

June 6, Jazz on the Hill. Celebrate 20 years of world-class music at Jazz on the Hill 2026 at College of San Mateo, a free all-day festival featuring acclaimed jazz artists, emerging young talent, and a vibrant community atmosphere on the hillside campus.

June 6, World Cup Event. Celebrate the excitement of the World Cup at Hillsdale Shopping Center in San Mateo with a family-friendly soccer celebration featuring interactive games, photo ops, vintage jerseys, custom duffle bag making, raffles, giveaways, and more.

June 6-July 25, Camp Pinstripes. Make the most of summer Saturdays at Camp Pinstripes in San Mateo, where kids can enjoy free hands-on activities like tie-dye, friendship bracelets, magic shows, princess visits, and more, plus complimentary brunch every week in June and July.

June 13, Pride in the Park. Celebrate inclusivity and show support for our LGBTQIA+ community with music, resources, performances, and group art projects in San Carlos.

June 13, Biggest Little Air Show.RC aircraft, drones, and flight demonstrations at the Hiller in San Carlos. This is one of the best little airshows in California.

June 14, Matcha Strawberry Roll Cake.Join an intimate, hands-on baking class in San Mateo where you’ll learn to create a stunning matcha strawberry roll cake with a light “no crack” chiffon sponge and fresh whipped cream filling and leave with your own party-sized dessert to take home.

June 18-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.

June 20, Barbie Truck. The Barbie Truck is rolling into Hillsdale Shopping Center in San Mateo, bringing exclusive Barbie merchandise and photo-worthy fun to the North Block Plaza near Cinepolis and Flores.

June 20, 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.

June 20-21, Clay as Canvas with Shanna Fliegel. This immersive two-day workshop at Clayroom in San Mateo invites participants to explore clay as both form and canvas for personal expression.

June 24, Community Hike. Enjoy a guided hike through the beautiful open spaces of Hidden Canyon Park in Belmont, where recreation staff will lead the way while sharing brochures featuring local trails and seasonal wildflowers.

June – August, 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.