The September Event Round-Up

September brings a change of season as well as a sizzling line up of autumn activities! Pack your month with Woodstock and Autumn Moon Festivals + Oktoberfest, food truck round-ups, workshops, farm fresh finds, hiking, yoga, park playtime 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 map out your month now.

September 1 Woodstock 50th Anniversary Festival. Students from the San Mateo Chapter, and other Bay Area Schools of Rock will perform songs from the legendary line-up at the Foster City Amphitheater.

September 1, 8, 15, 22, 29, Farmers Market Bay Meadows. Shop the market, enjoy live music, catch kids activities at Sweet Peas Tent hosted by Little Wonders San Mateo, plus park your pooch at the #PoochPitStop hosted by our friends at For Sniffs and Giggles! Every Sunday on the corner of E. 31st and Delaware Streets in San Mateo from 9:30am – 1:30pm (Rain or Shine).

September 4, 11, 18, 25, Off the Grid: Foster City. Live entertainment and food trucks return to Leo Ryan Park every Wednesday night.

September 5, 12, 19 Join the fun as The City of San Mateo celebrates its 125th Anniversary with September Nights on B Street! Thursday night attendees will enjoy pop-up dining, drinks and dancing between 5-8pm in the heart of downtown San Mateo throughout September.

September 5, Kokedama Workshop. Come and enjoy making Kokedama, a handcrafted moss ball at the Foster City Library.

First Thursday September 5th, Twilight Tails. Join the line-up of professionals that cater to your canines and enjoy a romp in the park with other pet parents. Create Yappy Hour by inviting your favorite four-legged pals for a romp in the park at Bay Meadows every Thursday evening from 6-7pm in Landing Green Park (Sept 12,19, 26).

September 6, First Friday Family Night. Join CuriOdyssey to learn about Seafood Watch, snack on Pacific Catch sustainable seafood samples and learn what animals eat. Grandparents admitted free this night.

September 6, Free First Friday. Explore the History Museum in Redwood City, enjoy Playing in the Past and a General Tour.

September 6 First Friday Art Series: Paige Mason. Take in an exhibit, art activity based on Paige’s work, and refreshments at the Burlingame Main Library.

September 7 Take A Hike: Coyote Point. Kick off hiking season with a 2 mile loop along the Bluff and Bay Trails at Coyote Point Recreation Area in San Mateo.

September 7  PHS/SPCA Mobile Pet Adoptions. First Saturday of the month @ 12-2pm at Hillsdale in San Mateo.

September 7 Pub in the Park. Imagine a leisurely summer afternoon, lounging in a park, while listening to live Americana and Bluegrass music, sipping delicious local brews and enjoying lawn games.

September 8 YOGA+DJ+BEER. Spend your sunny Sunday afternoon with yoga teacher Tony Irwin and live DJ Don Kainoa for a laid back 90-minute yoga class at Devil’s Canyon Brewing in San Carlos.

September 8, 15, 22, 29, Bicycle Sundays. Weekly on 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 including jogging, bicycling, hiking, roller-skating, and walking.

September 14 Tacos & Tequila. Get ready for delicious tacos, margaritas and outdoor festivities in Hillsborough.

September 15 San Mateo Autumn Moon Festival. Spend a beautiful Autumn morning at the picturesque San Mateo Central Park and support healthy living for seniors and all generations!

September 18 Take A Hike Weekday: Coyote Point. Take a 2-mile loop along the Bluff and Bay Trails at Coyote Point Recreation Area in San Mateo.

September 19 Pink Pamper Party. Enjoy a session of indulgence and relaxation at Hillsdale Shopping Center with special treatments, tasty treats and beverages, along with live DJ music to sooth the soul.

September 21 Annual San Mateo County Disaster Preparedness Day. Explore fire trucks, SWAT & other emergency response vehicles, attend classes on CPR, First Aid & more.

September 25-29 Oktoberfest. Redwood City brings a fabulous traditional German Oktoberfest setting and live entertainment to Courthouse Square.

September 29 Family Fun Faire. Spend an afternoon of family fun and entertainment at Devil’s Canyon Brewing Company in San Carlos.

Conveniently located between San Francisco and Palo Alto in San Mateo, Bay Meadows offers new homes for sale and for rent within walking distance of Caltrain. Ease of transportation is only one reason you’ll fall in love with Bay Meadows. Smartly-designed, high-quality new homes sit among 18 acres of open space, which includes parks, a community garden, public art, ball fields, bocce and basketball courts and a new playground. All this just a walk from Whole Foods, Blue Bottle Coffee, Fieldwork Brewing Co., LIFT Fitness, Tin Pot Creamery, Hillsdale Shopping Center and more. Learn more about what Midurban life offers by following our Facebook page.