Join The City of San Mateo's Parks & Recreation Department and the Downtown San Mateo Association for a BOO-tiful day in Downtown San Mateo on Saturday, October 26 from 3:00-5:00pm! Live DJ music, photo booth, kid’s activities, pumpkin decorating, crafts, and more! Put on your FANG-tastic costume and Trick-or-Treat at San Mateo businesses! We hope […]

*** This event has unfortunately been cancelled due to inclement weather. Stay tuned for a make up date, and we'll see you on December 22nd!! *** The Holiday season is […]

Downtown San Mateo Association presents: a special Small Business Saturday Jazz on B Street featuring The Sizzling Cactuses Date: Saturday, November 30th Time: 1:00 PM - 3:00 PM Location: B […]

The Holiday season is HERE! Visit Downtown San Mateo's B Street for HEAD WEST Marketplace on Sunday, December 8 and Sunday, December 22! Browse unique holiday gifts or find a treat for yourself from 50 local Makers, Merchants, Crafters, Designers, and Artists. While you're here, explore Downtown’s retail offerings, and enjoy delicious food from our […]

🎶 Sounds of the Season in Downtown San Mateo! 🎄 Get into the holiday spirit with live music this December 8th! Join us for two festive pop up performances: ✨ 1:00 PM - Enjoy the smooth holiday harmonies of talented a cappella group, Business Casual ✨ 5:30 PM - Be enchanted by the beautiful voices […]

The Holiday season is HERE! Visit Downtown San Mateo's B Street for HEAD WEST Marketplace on Sunday, December 8, and Sunday, December 22! Browse unique holiday gifts or find a treat for yourself from 50 local Makers, Merchants, Crafters, Designers, and Artists. While you're here, explore Downtown’s retail offerings, and enjoy delicious food from our […]

Start the new year on a high note! Join us for Jazz on B Street on Saturday, January 11th, as we welcome Swingatto, a dynamic Swing and Gypsy jazz trio, to Downtown San Mateo! From 1-3pm, let their lively melodies transport you to another era while you enjoy a delightful afternoon in the heart of […]