4th Sundays

November & December — 11a-4p

Downtown San Mateo features a bustling restaurant scene and thriving retail community all tucked into just five square blocks. You can’t possibly cover every dining and boutique experience represented Downtown in one visit, and that’s a good thing – because there’s so much here to keep you coming back.

The diversity of our Downtown entertainment and shopping options is unique for a city of our size. And so is the quality – which you can taste every night at our Michelin-starred eateries. Read about a few of our Downtown business owners’ commitment to quality and passion for making the heart of our city stronger.

Downtown San Mateo is conveniently located in the heart of the Peninsula, yet worlds away from the hustle of the rest of the Bay. Explore the many sides of our five square blocks brimming with over 100 dining destinations, shopping experiences and local art, in ideal weather day or night.

Each marketplace is light rain or shine.

All outdoor venues are kid + pet friendly, with ADA Accessible entrances and maintained portable/public restrooms for use.

Find directions HERE, with free parking available. Public Transportation, Ride Share or Bike/Scooter is also recommended.

While we may be out of a global pandemic, HEAD WEST is committed to following any and all federal, state and local ordinances as it relates to masking, physical distancing, hand sanitizing and other safe guards.

As always, we will look out for the best interests, health and well-being of our Team, Participants & Patrons.

Additionally, Participants reserve the right to enforce their own rules within their given booth spaces (i.e. asking Patrons to wear a mask, distance, sanitizing, etc).