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“Soak Up the Sun” Downtown in July

June was really busy Downtown, with a Downtown Historic District Heritage Tour, a Soccer Social Pop-Up and a Watch Party, the Central Park Music Series, the Pride Celebration, and the return of our monthly HEAD WEST Marketplace.

We were also featured on ABC7News! Read about it, and see the video here: Downtown San Mateo’s revival is a playbook for other California cities.

This month we have our second Soccer Social Pop-Up, Fit Fest, Bay Area Moms Back to School Bash, HEAD WEST, and Jazz on B with Melodic Outreach Endeavor. The Central Park Music Series continues all month, and local businesses are hosting soccer watch parties.

Our neighorhood is so fun and vibrant with the Farmers Market, comedy, live music, dance parties, karaoke, and trivia.

Follow us on Facebook and Instagram so you don’t miss a thing. 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. Our past newsletters are even hanging out in our archive. Thank you for continuing to show up for our small business community!

Photo credit: @jennyli.photos

Bay Area Fit Fest

The Bay Area’s largest outdoor fitness festival is back! Join the fun at Central Park on Saturday-Sunday, July 11–12, from 10am-3pm, for a high-energy weekend. The event will feature 10 signature workouts, live DJs, a Lululemon-sponsored Lagree Microformer experience, and 40+ fitness, wellness, recovery, and beauty activations. Discover local studios, try the latest wellness trends, enjoy interactive experiences, and connect with the Bay Area’s vibrant fitness community. Whether you’re a fitness enthusiast or simply looking for a fun summer weekend, Bay Area Fit Fest has something for everyone.

Find more details and get tickets on the event page.

Central Park Music Series

The Central Park Music Series continues this month. Spend your Thursday evenings through August 6 (no concert on July 4) enjoying free music in the park, family-friendly activities, local food vendors, and quality time with friends and family. These weekly gatherings are a great way to connect with your community and truly enjoy a beautiful summer in San Mateo.

Don’t forget about the special 4th of July celebration at Central Park on Saturday, July 4.

More information here.

Bay Area Moms Back-to-School Bash

Join Bay Area Moms for an edu-taining bash on B Street! Try your hands at arts & crafts, skill games, STEM/sensory play, and activities for all ages. Pick up a goodie bag with back-to-school goodies and connect with mom-approved local businesses.

This event is free, with street parking nearby. Swing by, rock out, and celebrate back to school! Activities and goodies will be offered while supplies last, so come early for the best opportunity to participate.

HEAD WEST Marketplace

HEAD WEST Marketplace returns to B Street on Saturday, July 18, from 11am to 5pm.

Visit 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.

• July 1 – Soccer Social Pop-Up (B Street)
• July 2 – Wildstyle Karaoke (McGoverns)(every Sunday and Thursday)
• July 3 – Karaoke (Blue Moon Bar)(every Wednesday and Friday)
• July 3 – Bachata/Salsa Social Dance Party (Motion Arts Center)(every Friday)
• July 4 – 4th of July in the Park (Central Park)
• July 5 – Gratitude Meditation (Chill Spot Rendezvous)
• July 6 – Mural Celebration (Mi Rancho Supermarket)
• July 6 – Swing Social (Motion Arts Center)
• July 7 – House of Samba Kids! (Main Library)
• July 7 – Trivia Tuesdays (McGoverns)(every Tuesday)
• July 8 – Sunset Trivia (O’Neill’s)(every Wednesday)
• July 9 – Central Park Music Series (also July 16, 23, 30, August 6)
• July 10 – Monthly Friday Night Dinner Dance (Peninsula Italian American Social Club)
• July 11 – Mixology 101 Class (Fogbird)
• July 11 – Wedding First Dance Workshop (Motion Arts Center)
• July 11 – 4 Week Series: Bachata Footwork & Partnerwork (Motion Arts Center)(also July 18, 25, August 1)
• July 12 – Downtown Historic District Walking Tour (San Mateo Heritage Alliance)
• July 12 – Rethink Your Lawn / Master Gardener Plant Clinic (San Mateo Arboretum Society)
• July 14 – Adventure Theater! (Main Library)
• July 18 – Growing Herbs for Flavor and Fun (Main Library)
• July 20 – NorCal Bats! (Main Library)
• July 21 – The Wylding Woods! (Main Library)
• July 24 – PIASC Goes Country (Peninsula Italian American Social Club)
• July 25 – Jazz on B Street with Melodic Outreach Endeavor
• July 25-26 – Citywide Garage Sale
• July 28 – SF Giants Italian Heritage Night (Peninsula Italian American Social Club)
• August 2 – Save the Date: Downtown Express
• August 16 – Save the Date: Central Bark
• September 4 – Save the Date: Movies in the Park
• September 26 – Save the Date: September Arts & Culture Fest

tinyB chocolate

411 S. B St.

• Check out Amici’s monthly promotions on their social media. Promo is valid on orders placed via amicis.com or the mobile app. No code needed

• Live music is back Friday-Saturday nights at B Street & Vine

• Tickets are on sale for Cinemark Century San Mateo 12‘s Summer Movie Clubhouse. Through Thursday, August 6, 10 weeks of Mega-Fun Movies for Kids, just $1.75 per movie

• You can rent machines from Clawesome for your event, and they can even be fully customized. (They also offer in-store events)

• Society of St Vincent de Paul of San Mateo County has a special promotion at their Downtown store through July 31: $10 off a purchase of $30 or more with promo code FIFA2026

• At tinyB chocolate, after 5:30pm, buy one cookie, get one free

• Y Salon Spa has Happy Hour Monday-Thursday 10am-3pm. Join them for complimentary drinks and service specials. They also offer free haircuts with a rising stylist on Tuesdays

• Welcome to the neighborhood: DoHo, How About Dance, Mini Market Mary’s

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

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 – This Southeast Asian ingredient is leading the next flavor trend in Silicon Valley (Avenida, Fogbird)
• KQED – 3 Under-the-Radar Bay Area Rose Gardens to Stroll for Free This Summer (Central Park)
• San Francisco Chronicle – Is this the Bay Area’s best jasmine milk tea? (Molly Tea)