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May Fun Downtown

April was a whirlwind of energy. We saw the return of the HEAD WEST Marketplace on B Street and an incredible turnout for our 3rd Annual Boba Day. Whether you joined us for Easter festivities, laughed at a comedy night, or discovered a new favorite vendor at the Farmers Market, thank you for making our streets so vibrant.

The momentum isn’t slowing down. May is packed with reasons to visit, including our Mother’s Day Pop-Up, another round of HEAD WEST, and the kickoff of the Love Local Summer Festival.

Want to stay in the loop? Make sure you’re following us on Facebook and Instagram. You can also head over to DSMA.org, which serves as your ultimate Downtown guide. There, you can explore our Events Calendar, Restaurant Guide, and even a Historic Walking Tour. Thank you for continuing to show up for our small business community!

Photo credit: Salena Chiang @sugarspice.realestateadvice

Mother’s Day Pop-Up

Treat the moms in your life this Mother’s Day! As an added incentive to celebrate Mother’s Day in Downtown San Mateo, DSMA is hosting the following on B Street on May 10, from 12-2pm:

• Free family photos* (1 printout for each mother, with digital copies available after the event)
• Special Jazz on B Street performance by Swingatto

Mom of 3, mom-to-be, dog mom, grandma – moms and families of all types are welcome!

Need help deciding where to make brunch or dinner reservations? Check out our Downtown San Mateo Restaurant Guide!

*Details may change in case of inclement weather. Photos are first come, first served, while supplies last

Love Local Summer Festival

Your new favorite summer afternoon is happening on Saturday, May 30, from 1-5pm.

Love Local Summer Festival by Celery Retail is taking over B Street in Downtown San Mateo with an incredible lineup of local brands, a dedicated vintage corner, live DJ, and good energy for everyone. Whether you’re shopping, exploring, or just soaking up the vibe, there’s something here for you.

Come out, shop local, and celebrate the community that makes San Mateo special. 

Find details here on how to participate.

AAPI Heritage Month Celebration

The Asian American and Pacific Islander (AAPI) Heritage Month Celebration will take place at Central Park on Saturday, May 2, from 12-3pm.

Celebrate, honor, and amplify AAPI heritage with fun activities, including:

• Live Demonstrations of Hula, Tai Chi, Kendo, and Japanese Calligraphy.
• Food Vendors 
• Arts & Crafts 
• Resource & Community Booths 
• Koi Fish Feeding at the Japanese Garden 

This event is hosted by the City of San Mateo Parks and Recreation Department. More details here.

HEAD WEST Marketplace

HEAD WEST Marketplace returns to B Street on Saturday, May 16, from 11am to 5pm.

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!

Apply now to join the HEAD WEST Family of local makers, crafters, artists, designers, and small biz merchants for 2026 dates.

• May 1 – Monthly Friday Night Dinner Dance (Peninsula Italian American Social Club)
• May 1 – Bachata Social Dance Party (Motion Arts Center)(also May 15)
• May 1 – Karaoke (Blue Moon Bar)(every Wednesday and Friday)
• May 1 – Tokie’s Cocktail Lounge (Tokie’s)
• May 2 – Free Comic Book Day (Main Library)
• May 2 – Free Community Skin Cancer Screening (Dorothy Schneider Cancer Center/Mills Peninsula Medical Center)
• May 2 – Pause, Sip, Explore… Bubbles & Rose (Pausa)
• May 3 – Gratitude Meditation (Chill Spot Rendezvous)
• May 3 – Compost Happens! / Master Gardener Plant Clinic (San Mateo Arboretum Society)
• May 3 – Family Approved Secret Movie Series (Cinemark Century San Mateo 12)
• May 3 – Wildstyle Karaoke (McGoverns)(every Sunday and Thursday)
• May 4 – May the 4th Be With You! (Main Library)
• May 4 – Swing Social (Motion Arts Center)
• May 5 – Cinco de Mayo Special Cumbia Class and Dance Party (Motion Arts Center)
• May 5- Trivia Tuesdays (McGoverns)(every Tuesday)
• May 6 – One Book One Coast Book Club: George Takei’s They Called Us Enemy – Book Discussion (Main Library)
• May 6 – Sunset Trivia (O’Neill’s)(every Wednesday)
• May 8 – Salsa Social Dance Party (Motion Arts Center)(also May 22)
• May 9 – Cocktail Masters Class: Advanced Mixology (Fogbird)
• May 9 – Calabria Night Dinner Dance (Peninsula Italian American Social Club)
• May 11 – Secret Movie Series (Cinemark Century San Mateo 12)
• May 16 – Wedding First Dance Workshop (Motion Arts Center)
• May 22 – Ladies Bunko Night (Peninsula Italian American Social Club)
• May 25 – Memorial Day Wreath-Laying Ceremony (Central Park)
• May 30 – Mixology 101: Classic Cocktails (Fogbird)
• May 30 – Milonga Sentimental Tango Party (Motion Arts Center)
• May 31 – One Book One Coast Book Club: George Takei’s They Called Us Enemy – Q&A with George Takei via Zoom (Main Library)
• June 12 – Save the Date: Soccer Social Pop Up
• June 13 – Save the Date: San Mateo County Pride Celebration
• June 25 – Save the Date: USA Soccer Watch Party

Rise Woodfire

2 N. B St.

• Amici’s has these promotions in May: Star Wars Day Monday, May 4: Enjoy $10 off any Large New York Style Pizza on dine-in and pickup orders when you mention this promo or use code FOURTH at checkout via amicis.com or mobile app. Items of the Month: 20% off their Items of the Month: The NEW Pesto-Roni Pizza, and NEW Chopped Italian Sub Sandwich. Promo is valid on orders placed via amicis.com or the Amici’s mobile app. No code needed

• Enjoy B Street & Vine‘s dog-friendly back patio while celebrating Happy Hour Tuesday-Saturday 3-6pm

• Hassett Hardware offers Handyman Services for residences and businesses throughout San Mateo County

• Manyak Dental Group joined the list of Age-Friendly Businesses in San Mateo. Here’s a Directory and more information about the program

• McGoverns is now open Monday-Saturday at 5pm, Sunday at 7pm

• Motion Arts Center has added Yoga for Dancers classes to their schedule

• OLHSO House, Pausa, and Rise Woodfire are all celebrating Mother’s Day with special menus on Sunday, May 10. Porterhouse will be serving their full dinner menu from 2-9pm

• Porterhouse is honoring the Class of 2026 with a $40 gift card. From now through July 1, enjoy $40 off any entree for the graduate during your celebratory meal

• Celebrate Cinco de Mayo at Rise Woodfire with $10 Margaritas and $1 off all Mexican Beers

• Sama Coffee Shop‘s hours are Monday-Thursday 7am-8pm, Friday-Saturday 7am-9pm, Sunday 8am-9pm

• Effective Friday, May 1, St. Vincent de Paul’s thrift store will be open from 10am-6:30pm Monday-Saturday

• Congratulations to Urban Ritual for winning “Judges’ Choice 2026” award and to TP Tea for being voted “Downtown San Mateo’s Favorite Boba 2026” at our Boba Day 2026!

• Welcome to the neighborhood: Coin Gold & Stamp Buyer, Mahasan, Mi Tienda

Downtown San Mateo Farmers Market

The Downtown San Mateo Farmers Market has moved to Thursdays, 3-7pm. It continues to be held in the Draeger’s parking lot (222 E. 4th Ave.)

Stay Connected with the City — Introducing My San Mateo

Want an easier way to report issues, request City services, and stay connected—all in one place? The My San Mateo App and Website is your hub for quick, convenient civic engagement.

With My San Mateo, you can:

• Report issues like potholes, broken streetlights, and more
• Track the status of your service requests in real time
• Receive notifications when there are updates
• Stay connected and help keep San Mateo running smoothly—from your phone or computer

Whether you’re out in the neighborhood or at home, My San Mateo makes it simple to stay informed and take action. Visit the website to learn more

Pedestrian Safety Improvements Downtown

New pedestrian safety barriers were installed in March on 1st & 3rd Avenues and B Street.

These barriers are at the intersection of the pedestrian mall where vehicle exposure is highest, giving pedestrians extra protection. Nearby, blue bike-locker–style cabinets let City staff move and manage the barriers as needed. These enhancements help keep our Downtown vibrant and safe for everyone who lives, works, and visits here

Free Downtown Parking

Parking is FREE Downtown on Sundays and after 6pm every day. Find more information here. (Please note that this does not apply to private lots)

• The Almanac – Half Moon Bay brunch destination Johnny’s now open in San Mateo
• Hoodline – Butter Bomb Buns: Pineapple King Bakerty Rolls Into Downtown San Mateo
• Palo Alto Online – Coming soon to downtown Palo Alto: hot chicken, Turkish breakfasts, and more ( Mahasan)
• Palo Alto Online – Palo Alto’s Reposado brings Mexican fine dining to downtown San Mateo
• San Mateo Daily Journal – San Mateo celebrates 3rd annual Boba Day with contest and activities
• Scot Scoop News – From home digest: Sweet Moment edition