Bay Meadows

May your month be filled with fun! We’ve rounded up an agenda packed with activities including Bike Month events, ping pong nights, live music, workshops, biking and hiking events, and much, much more at Bay Meadows and beyond. When you live just steps from Caltrain it’s easy to get from here to ‘there’ car-free! Get the Hillsdale Caltrain schedule here. Explore our roundup and plan your month.

Bicycle Sundays. 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.

May 1, Edgewood Park for Beginning Birders, San Mateo County. Take the Clarkia Trail through grassland, chapparal, and oak habitat while looking for resident birds and visiting spring breeding birds.

May 2, Yoga in the Bungalow. This one hour class in Redwood City is intended to increase your flexibility, strength and balance.

May 5, Family Ping Pong Night: Star Wars Night! There will be an option Jedi Tournament for those who love a fun competition. Dress up in your favorite Star Wars gear and get free open play passes in Burlingame.

May 5, Free First Friday. Admission is free at the SMC History Museum in Redwood City. Online, preschoolers can listen to a story and make a craft. Docents will also lead an online tour of the Museum.

May 5, First Friday Nights. Swing into the weekend with music, science, animals and fun! On the first Friday of every month, from 5 pm until 8 pm, where parents and kids celebrate together at CuriOdyssey.

May 6, Take A Hike Challenge 2023: Sawyer Camp South of Dam Trail. Hike begins at 9am at the Sawyer Camp Trail Southern Entrance, offering a 2.4 mile hike along the trail South of Crystal Springs Dam.

May 6, Live Music at MidiCi. Join MidiCi for the debut performance of Red Vinyl, a local band covering dance music from Elvis to Pitbull. Enjoy authentic Italian cuisine while indulging in great music.

May 6, Pinewood Derby Finals. Ready, set…race! Watch these tiny wooden cars tear up the track in Nordstrom Court at Hillsdale. Hosted by The Boy Scouts of America and Pacific Skyline Council.

May 6, Shakespeare on Tour’s ‘A Midsummer Night’s Dream’. All are invited to attend SF Shakespeare Festival’s touring performance of this antic comedy. Admission is free, courtesy of the Belmont Library.

May 7, Popular Houseplants. Learn to propagate houseplants and then go into specific “categories” of houseplants in San Mateo.

May 9, lululemon Burlingame Run Club. From beginner to expert, strollers to dogs, there’s a place for you at Run Club. Join the run, walk, jog and connect with the Burlingame store team and community.

May 11, Art on the Runway. Watch art parade by on the runway while enjoying wine, a signature cocktail, and an in-flight menu of international hors d’oeuvres in San Carlos.

May 13,  Happy San Mateo County Day. Celebrate San Mateo County’s birthday with an exploration of our past! The theme of this year’s birthday party in the Aughts (decade of 1900-1909) with craft activities of the era.

May 13, “Almost” Mother’s Day Kids Concert. Families will enjoy a kids concert with Andy Z and the Andyland Band, an inflatable playland, and can also create a Mother’s Day Gift in the craft area in Redwood City.

May 13, Mother’s Day Flower Arranging Workshop. In this hands-on experience at luludi living art in San Mateo, you will learn how to put together your own succulent terrarium inside a glass vessel.

May 13, Patchwork Show Makers Market. Market featuring 100+ local makers, crafters, junior entrepreneurs, designers, and food artisans, all surrounded by downtown Redwood City restaurants and shops.

May 13, Mental Health and Wellness Walk. De-stress at the San Mateo Youth Commission Mental Heath and Wellness Walk in San Mateo. The event is open to everyone, and food will be provided.

May 14, Mother’s Day Terrarium and Brunch Experience. Join luludi living art for an annual celebration and create beautiful flower arrangements while you enjoy brunch at this workshop in San Mateo.

May 14, Kids Carnival. Aircraft checkouts, cockpit exploration, glider and helicopter construction and more are just some of the activities available at the Hiller Aviation Museum in San Carlos.

May 17, Hirsch Vineyards Wine Dinner. A dinner featuring a special selection of Hirsch Vineyards’ wines paired with a multi-course menu in Redwood City.

May 18-20, Bike Wherever Days return to the San Francisco Peninsula and Silicon Valley! Pledge to ride. Just by biking, you’ll be helping SVBC on its mission to build healthier and more just communities. The celebration is happening all through May. See all Bike Month events.

May 18, Bike Bash San Mateo. Come as you are and enjoy food, beverages and merriment with your fellow bike commuters at the San Mateo location.

May 19, Chocolate Truffle Workshop & Beer Pairing. Follow instruction by Chef Teena at the Chocolate Truffle Workshop at Devil’s Canyon Brewing Company in San Carlos.

May 19-27, Eat Local! Peninsula Restaurant Week. This week, grab a meal to-go or make a dinner date with family or friends. This is your opportunity to check out new restaurants and specials.

May 20, Bike Ride to Tour the Many Murals of Redwood City. In celebration of lovely weather, community artwork, and Bay Area Bike To Wherever Days, hop on two wheels and enjoy a free, open-to-the-public group bike ride to meet artists, tour various murals, and get some exercise and fresh air with friends.

May 21, The Silicon Valley Whisk(e)y Festival. The whiskey festival The Bay Area has been waiting for is finally here! Join Domenico Winery in San Carlos for a delicious array of whiskeys from around the world.

May 25, Pause for a Wine Dinner with Vignalta. Join Chef Andrea in San Mateo for a four course tasting dinner to pair with an amazing collection of wines from Vignalta.

May 26, FoodieLand Night Market. FoodieLand is a three-day outdoor multicultural food festival for foodies in San Mateo. Featuring over 170+ vendors in attendance.

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.