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May in the Bay Meadows area is jam packed with moments that bring together culture, creativity, food, and family-friendly fun all across the Peninsula. From hands-on science and animal encounters at San Mateo’s CuriOdyssey to local history experiences at the San Mateo County History Museum, weekends are filled with opportunities to explore, learn, and connect.

This month also highlights vibrant neighborhood gatherings like Clayroom San Mateo’s Spring Craft Fair, game day and movie popups on the big screen at Fieldwork San Mateo Beer Garden, and street eats arriving moments from home. LFBA Studios is now open in Bay Meadows Town Square, give them a follow at @lfbastudios today for the latest San Mateo studio updates, special offers and fun events. And, Basecamp San Mateo is kicking off a Summer Stretch promo: 1 week of unlimited classes for just $29.99! (That’s less than the cost of a single drop-in class.) And here’s the bonus: Exclusive discounted membership rates for Bay Meadows residents. Spots fill quickly, don’t wait. Claim your week and get started today HERE. *New Members only!

Don’t miss AAPI Heritage Month celebration at Central Park, San Mateo and the culinary adventures during Taste of the Peninsula. Families can also look forward to outdoor festivals, interactive museum days at the Hiller Aviation Museum, and wellness-focused events at scenic spaces like Coyote Point Recreation Area and Seal Point Park.

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.

Whether you are planning a weekend outing, a creative class, or a community celebration, May offers something for everyone to enjoy just minutes from home.

May 1, 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!

May 1, 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.

May 1-3, Taste of the Peninsula. Explore the culinary landscape of San Mateo County at this week of special prix fixe menus at hundreds of restaurants. The first half of the festival will focus on the San Francisco Peninsula’s “bayside” restaurants while the second half on the area’s “coastside.”

May 2, AAPI Heritage Month Celebration. Join the celebration of AAPI Heritage at Central Park in San Mateo (50 E. 5th Avenue), featuring live cultural demonstrations, traditional food, arts and crafts, community booths, vendors, and more in a vibrant community gathering.

May 3, Spring Craft Fair at Clayroom San Mateo. Mix with neighbors and shop member-made art from 11am–4pm @ 3050 S Delaware St in Bay Meadows neighborhood. Find handmade ceramics, knits, baked goods, cards and more just in time for Mother’s Day!

May 3, Plant Sale & Craft Fair. Join the annual free Plant Sale & Craft Fair at the San Mateo Garden Center, located at Alameda de las Pulgas and Parkside Way near Beresford Park in San Mateo, for a community event featuring plants, crafts, and local vendors.

May 5, Improv Tuesdays. Enjoy an evening of fun improv games (no performing/no audience) at Twin Pines Manor in Belmont. This event will be held every month on the 1st and 3rd Tuesdays from 6-8pm. Bring snacks to share!

May 6, Spark & Shimmer. Join the 16th Annual CuriOdyssey Benefit in San Mateo for an inspiring evening at the museum and zoo, where community supporters come together to celebrate and raise vital funds that help ensure all children have access to joyful, hands-on science learning and discovery.

May 8-9, Porcelain Surface Stories w/Jason Walker. Join a dynamic two-day workshop at Clayroom in San Mateo with Jason Walker, where participants will explore his 30-year approach to blending imagery and form in dimensional ceramics. Working with porcelain, you’ll create functional pieces using wheel throwing and slab handbuilding, then enhance them with expressive underglaze painting and surface design.

May 9, Made with Love: A Mother’s Day Collective. Celebrate Mother’s Day at Hillsdale in San Mateo with a thoughtfully crafted afternoon in our North Block Plaza. Featuring a selection of local vendors offering hands-on, Mother’s Day-inspired experiences such as floral arranging, candle making, charm jewelry creation, and more! Whether you’re looking to create a meaningful gift for or enjoy a memorable outing, this experience is the perfect way to honor and celebrate the special women in your life.

May 9, Almost Mother’s Day Concert. Enjoy a fun-filled morning in Redwood City where the whole family can enjoy live music from Andy Z and the Andyland Band, let the kids burn off energy in the inflatable play area, and get creative making a special Mother’s Day gift for someone they love.

May 10, Chocolate Tasting & Tempering. Learn the fundamentals of chocolate making in this hands-on class at Baking Arts in San Mateo focused on tempering techniques, tasting, and understanding chocolate science like viscosity, percentages, and temperature. Students will practice dipping and molding using both hobbyist and professional molds, enjoy a rocky road demonstration, and take home their own handcrafted chocolates.

May 10, Paint-A-Plane. Join the excitement at Hiller Aviation in San Carlos with special activities just for kids!  Paint the Cessna Cardinal, check out in an airplane or helicopter, and more!

May 15-17, Hometown Days. Live entertainment, extended hours of fun, games, rides, live music, and weekend-long activities and entertainment in Burton Park in San Carlos.

May 16, Soul Stroll 2026: Movement is Resistance. Gather at Coyote Point Recreation Area in San Mateo for a morning dedicated to fun, health, and community. This joyful community event includes a 1, 3, and 5-mile run/walk, along with a Community Health Village that showcases abundant resources and partners offering essential products, screenings, and information.

May 30, PAL’s 5K Run/Walk & 10K Run and Wellness Fair. This day at Seal Point Park in San Mateo is dedicated to supporting health and mental wellness, encouraging community partnerships and educating about diverse resources.

May 31, Glider Discovery. Learn the names of the different parts of the airplane, then join in the fun to help build a full-size Penguin airplane at Hiller Aviation in San Carlos. Then, assemble a balsa wood glider and join a fun festival of flight outdoors in the museum’s Courtyard.  Each child receives a glider to take home!

May/June 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.