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Summertime Fun Downtown in June

May weekends were so much fun with our Mother’s Day Pop Up, HEAD WEST Marketplace, and a Love Local Summer Festival. The month also included the AAPI Heritage Month Celebration at Central Park.

Now summer’s here, and our neighborhood is such a great place to be! June will be busy, with a Downtown Historic District Heritage Tour, a Soccer Social Pop-Up, the Central Park Music Series, the Pride Parade, and the return of the monthly HEAD WEST Marketplace.

Downtown San Mateo is always busy with the Farmers Market, comedy, live music, dance parties, karaoke, and trivia.

Make sure you’re following 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: Mia Torres (@miatorres.photo)

Soccer Social Pop-Ups

Catch pro soccer action on Friday, June 12, and Wednesday, July 1, from 5-8pm on the B Street pedestrian mall. Enjoy match-day specials, food, games, and a fun community vibe while supporting local businesses.

These events are brought to you by the City of San Mateo in partnership with DSMA and the San Mateo Area Chamber of Commerce.

Central Park Music Series

The Central Park Music Series returns this month! Spend your Thursday evenings 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.

• Thursdays from June 18-August 6 (no concert on July 2)

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

Stay tuned for the band line-up, food vendors, and activities. Updates will be posted here.

Best of San Mateo Area

Congratulations to the winners of Best of San Mateo Area 2026!

The full list of winners is here. An Awards Celebration will take place on Thursday, June 11.

Many of our Downtown neighbors were voted the Best:

Alborzi Orthodontics, Amici’s, Appelblom Jewelry, Aragon Veterinary Clinic, Assistance League of San Mateo Turnstyle Thrift Shop, Backhaus, B Street & Vine,

Chill Spot Rendezvous, Core Taekwondo, Fiori Dental, Fitphoria/Jennifer Slaboda, Fogbird, Footwear Etc., Gao Viet Kitchen,

Happy Mozart Music School, Hassett Ace Hardware, Mills-Peninsula Medical Center-San Mateo Campus, Nandi Yoga, Pausa,

Peninsula Eye Physicians & Surgeons,

Peninsula Family Service, Prometheus,

Rise Woodfire, Sage Wellness Center, Sibby’s Cupcakery, Spa Siam Orchid,

Taqueria Pancho Villa, Teaspoon, Tokie’s, and Verkada

HEAD WEST Marketplace

HEAD WEST Marketplace returns to B Street on Saturday, June 20, 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.

• June 1 – Swing Social (Motion Arts Center)
• June 1 – Secret Movie Series (Cinemark Century San Mateo 12)
• June 2 – Trivia Tuesdays (McGoverns)(every Tuesday)
• June 3 – Wine Dinner with Poggio Landi (Pausa)
• June 3 – Sunset Trivia (O’Neill’s)(every Wednesday)
• June 3 – Karaoke (Blue Moon Bar)(every Wednesday and Friday)
• June 4 – Letting Go of the Past, Stepping into the Future with Yogeswari: A Jivamukti Master Class on Forward Bending (Nandi Yoga)
• June 4 – Wildstyle Karaoke (McGoverns)(every Sunday and Thursday)
• June 5 – Monthly Friday Night Dinner Dance (Peninsula Italian American Social Club)
• June 5 – Bachata Social Dance Party (Motion Arts Center)(also June 19)
• June 7- Gratitude Meditation (Chill Spot Rendezvous)
• June 7 – San Mateo Downtown Historic District Walking Tour (San Mateo Heritage Alliance)
• June 7 – Habitat Gardening / Master Gardener Plant Clinic (San Mateo Arboretum Society)
• June 7 – Karaoke World Championships USA Auditions – Qualifier Round (McGoverns)(also June 11, June 14)
• June 12 – Salsa Social Dance Party (Motion Arts Center)(also June 26)
• June 12 – Trivia Night (Main Library)
• June 13 – San Mateo County Pride Celebration
• June 13 – Wedding First Dance Workshop (Motion Arts Center)
• June 18 – Central Park Music Series
• June 18 – Karaoke World Championships USA Finals (McGoverns)
• June 20 – Cocktail Masters Class: Advanced Mixology (Fogbird)
• June 22 – Cooking Demonstration Dinner (Peninsula Italian American Social Club)
• June 23 – Farmer Arann! (Main Library)
• June 24 – Teen Summer Party (Main Library)
• June 25 – Central Park Music Series
• June 25 – USA Soccer Watch Party (Central Park)
• June 27 – Smart Cycling Part 1 (Main Library)
• June 27 – BTS K-Pop Workshop (Motion Arts Center)
• June 27 – Summerween! (Main Library)
• June 30 – Things That Creep! (Main Library)
• July 1 – Save the Date: Soccer Social Pop-Up
• July 11-12 – Save the Date: Bay Area Fit Fest
• July 19 – Save the Date: Bay Area Moms Back to School Bash
• July 25 – Save the Date: Jazz on B Street with Melodic Outreach Endeavor
• July 25-26 – Citywide Garage Sale

A.S.K Salon

327 E. 4th Ave.

• Amici’s has these promotions in June: Father’s Day, June 21: Enjoy HALF PRICED WINGS on dine-in and pickup orders when you mention this promo or use code DAD at checkout via amicis.com or the Amici’s mobile app. Items of the Month: 20% off the NEW Salami Honey Pie, and famous Caesar Salad. Promo is valid on orders placed via amicis.com or the mobile app. No code needed

• A.S.K Salon is celebrating their 30th anniversary. Congratulations, A.S.K!

• The Barrel Bistro & Wine Bar is now serving breakfast

• CAM EDU’s and Core Taekwondo‘s registration for Summer Camp are open

• Tickets are on sale for Cinemark Century San Mateo 12‘s Summer Movie Clubhouse. From June 1-August 6, 10 weeks of Mega-Fun Movies for Kids, just $1.75 per movie

• Colander Kitchens is available to rent for corporate events, parties, and more

• Lion’s Den Shave Parlor has a new website

• Manyak Dental Group is open one Saturday each month. Call them to book a spot, or request an appointment online

• 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

• Whisper and Wunderbar have reopened

• Welcome to the neighborhood: Dollhouse Princess Boutique

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)

• Hoodline – New Thai Hotspot Mahasan Spices Up Downtown San Mateo
• KRON4 – Giants’ Jung Hoo Lee dines at Peninsula Korean BBQ Restaurant (OLHSO House)
• M-A Chronicle – Downtown San Mateo Boba Day Features a Playful Cultural Celebration (Boba Bless, Sharetea, Sweet Moment, Teaspoon, Tong Sui, TP Tea)
• Mercury News – New Thai restaurant debuts in downtown San Mateo (Mahasan)
• Palo Alto Online – Renowned restaurants, historic architecture and a car-free Corridor: Here’s what downtown San Mateo has in store (3 Bees Coffee, Akiba HQ Anime & Gundam Store, Amour Amour, Backhaus, The Barrel Bistro & Wine Bar, Chill Spot Rendezvous, Clawesome, Daeho Kalbijjim & Beef Soup, Dash Japanese Tapas & Sushi, Draper University, Espetus, Fogbird, Gao Viet Kitchen, Golden Moon Gallery, Honey and Hive, Izumi Matcha, Kajiken, La Pinata, O’Neill’s Irish Pub, Pausa, Plato’s Closet, Rise Woodfire, Sama Coffee Shop, San Mateo Arboretum Society, Sibby’s Cupcakery, SimplyCake, Tai Er, Takahashi Market, Therapy Stores, tinyB Chocolate, Wunderbar)
• The San Francisco Peninsula Magazine – Issue 2 (Backhaus, Kajiken, Pacific Catch, San Mateo Arboretum Society, Spa Siam Orchid, Sushi Yoshizumi)
• San Mateo Daily Journal – Downtown San Mateo ‘thriving’