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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.

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. 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.

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.

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.

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.