Sunset Trivia (at O'Neills)
2026-10-07 19:15 - 21:00, 2026-10-14 19:15 - 21:00, 2026-10-21 19:15 - 21:00 (America/Los_Angeles) | O’Neill’s Irish Pub, 34 South B Street, San Mateo, CA, 94401, United States
Unearth your team’s potential at O’Neills Irish Pub in San Mateo! This vibrant spot, perfect for continuing your evening, hosts exhilarating trivia every Wednesday at 7:15 PM. Gather your sharpest minds, join the craic, and put your knowledge to the ultimate test. Will you be the lucky team to claim victory?
This is a recurring event. Please check with O’Neills in case of cancellation or schedule changes.

Karaoke (at Blue Moon Bar)
2026-10-07 21:30 - 23:59, 2026-10-09 21:30 - 23:59, 2026-10-14 21:30 - 23:59, 2026-10-16 21:30 - 23:59, 2026-10-21 21:30 - 23:59, 2026-10-23 21:30 - 23:59 (Africa/Abidjan) | Blue Moon Bar, 215 S B Street, San Mateo, CA, 94401, United States
From Blue Moon Bar:
Join us every Wednesday and Friday at 9:30 PM with your host @xfallingstarx. Sing your heart out in the heart of Downtown San Mateo.

Happy Hour at Porter House
2026-10-08 16:30 - 18:00, 2026-10-15 16:30 - 18:00, 2026-10-22 16:30 - 18:00 (Africa/Abidjan) | Porterhouse, 164 S. B Street, San Mateo, CA, 94401
Join us at Porter House. Unwind after a long day of work and join us for Happy Hour Daily (Monday – Friday) from 4:30PM-6PM in our Bar and Patio, featuring drink specials, appetizers, and great service!
The DSMA calendar is intended to share the exciting events and promotions provided by our Downtown San Mateo businesses. We do our best to keep up with changes, but please always confirm details with the individual business.

Happy Hour at La Cumbre
2026-10-08 18:00 - 20:00, 2026-10-15 18:00 - 20:00, 2026-10-22 18:00 - 20:00 (Africa/Abidjan) | Taqueria La Cumbre, 28 N B St, San Mateo, CA, 94401, United States
Join us at Taqueria La Cumbre. Come every Thursday from 6:00PM-8:00PM and have any cocktail you want for $3.99!
The DSMA calendar is intended to share the exciting events and promotions provided by our Downtown San Mateo businesses. We do our best to keep up with changes, but please always confirm details with the individual business.

Karaoke at McGovern's
2026-10-08 21:30 - 23:59, 2026-10-11 21:30 - 23:59, 2026-10-15 21:30 - 23:59, 2026-10-18 21:30 - 23:59, 2026-10-22 21:30 - 23:59, 2026-10-25 21:30 - 23:59 (Africa/Abidjan) | McGoverns, 215 E 4th Ave, San Mateo, CA, 94401, United States
From McGovern’s:
Sing your heart out every Thursday and Sunday night at McGovern’s! We offer the best prices in downtown San Mateo with $6 well drinks and $7 draft specials starting at 9:30 PM.
The DSMA calendar is intended to share the exciting events and promotions provided by our Downtown San Mateo businesses. We do our best to keep up with changes, but please always confirm details with the individual business.

Salon Happy Hour Special (at Y Salon)
2026-10-12 10:00 - 15:00, 2026-10-19 10:00 - 15:00, 2026-10-26 10:00 - 15:00 (Africa/Abidjan) | Y Salon Spa, 241 S San Mateo Dr,, San Mateo, CA, 94401, United States
Take advantage of a special Happy Hour promotion at Y Salon & Spa! Happy Hour is available Monday through Thursday from 10:00 am to 3:00 pm. Join us for great complimentary drinks and service specials to get up to 20% off during these hours.
The DSMA calendar is intended to share the exciting events and promotions provided by our Downtown San Mateo businesses. We do our best to keep up with changes, but please always confirm details with the individual business.

Discount Tuesday (at Cinemark Century San Mateo 12)
2026-10-13, 2026-10-20 | Cinemark Century San Mateo 12, 320 East 2nd Ave, San Mateo, 94401, United States
From Cinemark:
TUESDAY MOVIE DEALS FOR ALL MOVIE LOVERS
EVERYONE SAVES!
Find Cheap Movie Theaters Near You
Discount Tuesday may not apply on or near holidays. See Cinemark for more details.
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.
https://www.cinemark.com/discounts/discount-tuesdays/

DSMA Board Meeting (Open to the Public)
2026-10-13 09:00 - 10:00 (America/Los_Angeles) | CA
The Downtown San Mateo Association Board and staff, representatives from the City of San Mateo, DSMA members, and other community members gather each month to discuss DSMA business.
If you have questions or to confirm the meeting location, please email us at HQ@dsma.org.
If you would like to make a presentation to the DSMA Board, reach out by email at least one month before the scheduled meeting.

Trivia Night at McGovern's
2026-10-13 20:00 - 22:00, 2026-10-20 20:00 - 22:00 (Africa/Abidjan) | McGoverns, 215 E 4th Ave, San Mateo, CA, 94401, United States
Join us for McGovern’s Trivia Night every Tuesday at 8:00 PM. Hosted by “Questionable Behavior with Misha,” come ready to play for prizes.
The DSMA calendar is intended to share the exciting events and promotions provided by our Downtown San Mateo businesses. We do our best to keep up with changes, but please always confirm details with the individual business.

HEAD WEST Marketplace
2026-10-17 11:00 - 17:00 (America/Los_Angeles) | B Street between 1st and 3rd Aves
Visit Downtown San Mateo’s B Street for HEAD WEST Marketplace on the third Saturday of every month in 2026! Browse unique gifts or find a treat for yourself from local Makers, Merchants, Crafters, Designers, and Artists. While you’re here, explore Downtown’s retail offerings, and enjoy delicious food from our local spots—there’s something for everyone!
More about HEAD WEST:

HEAD WEST provides a marketplace for emerging + established local brands and small businesses to have physical selling space multiple times per month at various neighborhood venues. From hand-made ceramics to locally sourced vintage, there are always new categories of goods available to explore. Connecting people, forging community + sustaining the local economy, we continue to build upon our presence by offering expanded resources for small businesses to learn, grow, connect + share. Interested in applying to be a HEAD WEST participant? Visit headwestmarketplace.com/apply
Need help finding your way to Downtown San Mateo? Visit our DIRECTIONS and PARKING pages
*Event details may change due to inclement weather.
