HEAD WEST Marketplace
2026-09-19 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.

Karaoke at McGovern's
2026-09-20 21:30 - 23:59, 2026-09-24 21:30 - 23:59, 2026-09-27 21:30 - 23:59, 2026-10-01 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)
2026-09-21 10:00 - 15:00, 2026-09-28 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)
2026-09-22, 2026-09-29 | 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/

Dance/Movement Therapy Support Group (Week 3) (at Tree of Life)
2026-09-22 19:00 - 20:00 (Africa/Abidjan) | Tree of Life Healing Center for the Soul, 316 S Eldorado Street, Suite 100, San Mateo, CA, 94401, United States
This 4-week support group invites participants to use dance and movement as creative tools and healing resources to connect with themselves and others. Facilitated by Nathaniel Silveira-Pyzik, a Licensed Professional Clinical Counselor and Board-Certified Dance/Movement Therapist, each session guides members through a structured warm-up, theme development, and closure. No prior dance experience is needed, and all movements can be fully adapted for physical impairments or disabilities. This group provides a non-judgmental, safe space for self-growth and healing from a variety of mental health or life issues. Participants must plan to attend all four sessions to maximize therapeutic benefit and group cohesion.
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.

Trivia Night at McGovern's
2026-09-22 20:00 - 22:00, 2026-09-29 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.

Sunset Trivia (at O'Neills)
2026-09-23 19:15 - 21:00, 2026-09-30 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)
2026-09-23 21:30 - 23:59, 2026-09-25 21:30 - 23:59, 2026-09-30 21:30 - 23:59, 2026-10-02 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
2026-09-24 16:30 - 18:00, 2026-10-01 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.

Music Bingo (at Chill Spot Rendezvous)
2026-09-24 17:30 - 19:30 (America/Los_Angeles) | Chill Spot Rendezvous, 271 Baldwin Ave., San Mateo, CA, 94401, United States
From Chill Spot Rendezvous:
2nd & 4th Tuesdays of the month 2-4pm Golden Oldies Senior Discount Day
Last Thursday of the month 5:30-7:30pm Variety Song List for Everyone!

Happy Hour at La Cumbre
2026-09-24 18:00 - 20:00, 2026-10-01 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.

Latin Night Dance Party (at Motion Arts Center)
2026-09-25 19:00 - 23:59 (America/Los_Angeles) | Motion Arts Center, 217 South Claremont Street, San Mateo, CA, 94401, United States
From Motion Arts Center:
Join us for our weekly Latin Night Dance Party filled with Salsa, Bachata, and Cumbia music!
Come, bring your friends and get ready for an unforgettable night of dancing and fun on the dance floor. We will provide snacks and light drinks.
The dance studio has air conditioning, a beautiful hardwood floor, colorful mood ambient lighting and a high quality sound system.
FRIDAY SCHEDULE:
7pm-8pm Latin Motion Fundamentals All Level Class
8pm-9pm Salsa Beginner Level Class
8pm – 9pm Bachata Beginner Level Class
9pm-12am Social Dance Party with Live DJ
TEACHERS: Tristan, Rhazel and Jesica

TICKETS PER PERSON:
$30 One single class session
$55 Two classes same day only
$15 Dance Party Only
*Social Dance Party is included when you take a class.

New Students Intro Offer: $65 7 Day Pass Unlimited For First Time Students Only (expires in 7 days, dance party is paid separately).
LOCATION:
Motion Arts Center
217 S Claremont St,
San Mateo, CA 94401

September Arts & Culture Fest 2026
2026-09-26 11:00 - 18:00 (America/Los_Angeles) | South B Street, South B Street (Between Baldwin Ave. & 2nd Ave.), San Mateo, CA, 94401, United States
From the San Mateo Area Chamber of Commerce (https://sanmateochamber.org/sept-fest/):

Save the Date! 2026 September Arts & Culture Fest

Mark your calendar for Saturday, September 26th, 2026, 11am – 6pm!
Join us in the heart of Downtown San Mateo for a fun day-long celebration of art, music, dance, poetry, food, and culture! From live bands and dazzling cultural performances to interactive kids’ activities, LIVE mural painting competitions, artists selling original handcrafted artworks, and poetry open mic, the September Arts & Culture Fest has something for everyone — and it’s completely FREE to attend.

Want to Be Part of the Fest?
I’m interested in a Vendor Booth
I’m interested in an Artist Booth
Sponsor the Event
Volunteer with Us
September Arts and Culture Fest is presented by the San Mateo Area Chamber of Commerce, County of San Mateo Office of Arts and Culture, & Downtown San Mateo Association.
Follow the Fest
Stay up to date on performers, artists, murals, and special announcements:

@smc_artsandculture
@sanmateochamber
@downtownsanmateo

Dance/Movement Therapy Support Group (Week 4) (at Tree of Life)
2026-09-29 19:00 - 20:00 (Africa/Abidjan) | Tree of Life Healing Center for the Soul, 316 S Eldorado Street, Suite 100, San Mateo, CA, 94401, United States

New Student Promo (at Motion Arts Center)
2026-10-01 - 2026-10-03 | Motion Arts Center, 217 South Claremont Street, San Mateo, CA, 94401, United States
From Motion Arts Center:
Special Intro Offer for New Students
7 Day Unlimited Pass for $65 per person (savings of up to $145!)
Expires 7 days from purchase
https://motionartscenter.com/new-students/

Welcome to Motion Arts Center!
We are thrilled to have you here at our beautiful studios in downtown San Mateo, CA.
We have a passion for dance and music and would love to share with you our experience and knowledge to make you a great dancer in a fun, comfortable and nurturing atmosphere! Whether you’re a total beginner student or an advanced level dancer enjoy learning from our friendly and professional teachers in our state-of-the-art dance studios.
Come and drop-in to any dance class, this means you can stop by at any time and choose from our diverse selection of group dance and fitness classes available throughout the day.
Online pre-registration and sign up is required for all in-person classes.
We look forward to seeing you in the studio soon!

*Terms and conditions may apply. Please see individual business for details.

Children's Bible Story Time (at Christian Science Reading Room San Mateo)
2026-10-02 10:30 - 11:30 (Africa/Abidjan) | Christian Science Reading Room San Mateo, 69 E 4th Ave, San Mateo, 94401, United States
Event from Christian Science Reading Room San Mateo
Join us for fun Bible stories! Children’s Bible Story Time takes place on the first Friday of every month at 10:30 AM. This community event is held at the Christian Science Reading Room in San Mateo. Location: 69 E. 4th Avenue, San Mateo, CA. For more information, call (650) 343-7332.
http://www.cschurchsanmateo.org/reading-room/

O'Neill's Presents: Fresh Fridays
2026-10-02 22:00 - 23:59 (Africa/Abidjan) | O’Neill’s Irish Pub, 34 South B Street, San Mateo, CA, 94401, United States
O’Neill’s Irish Pub presents “Fresh Fridays” featuring DJ Bucc Rogerz! Join us every 1st Friday of the month for a high-energy night of music. This is a 21+ event with no cover charge. The party starts at 10 PM at 34 S B St, San Mateo, CA 94401.
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.

Mixology 101 - Classic Cocktails
2026-10-03 14:30 - 16:00 (Africa/Abidjan) | Fogbird, 144 S B St, San Mateo, CA, 94401, United States
Join us at Fogbird for a Mixology 101! Fogbird cocktail classes are fun, educational and spirited. Our knowledgeable, well-trained bartenders walk you through a step-by-step process of how to build, shake and stir the perfect cocktail. You will leave with fun memories, and a recipe keepsake card. Ticket price starts at $93 and you must book online.
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.
