🗓️ Dad's Day Playbook + Weekend Outside

Good morning neighbors!

Thanks for all the feedback after last week’s launch, and for coming back for this weeks edition!

This week we’ve got all the events you need to celebrate for Father’s Day, details on Saturday’s Pride parade, and where to go for free outdoor music and movies for the family.

We’ll also cover updates on the recently approved transportation budget and early plans on where the funds will be spent.

Let’s get to it!

🚦Transportation Budget Greenlight

San Mateo County’s Transportation Authority just OK’d a $187.1 million 2026 budget aimed at unclogging commutes and funding safer ways to get around.

Expect fresh bike lanes, smoother Hwy 101 fixes and safer crossings — plus $300K for a Grand Boulevard revamp and $2 million in technical assistance to local agencies, all powered by sales-tax cash proceeds from Measures A / W. More here.

🚂 Hidden Caltrain Station Apartments

A former Caltrain station manager was just sentenced to jail and ordered to repay a restitution bill for secretly converting corners of the Burlingame and Millbrae stations into crash-pad apartments for himself and a Caltrain ex–operations chief — complete with a kitchen, shower and security cameras.

Despite Caltrain vowing tighter controls, the makeshift apartments still sit idle. Read more here.

✈️ Digital Passport Takes Off

TSA just cleared Apple’s upcoming iOS 26 Mobile Passport for use at SFO and every major California airport, so your iPhone (or Apple Watch) can double as a Real ID-compliant passport for domestic flights when the software lands this fall.

The digital ID is domestic-only and TSA still advises packing your physical passport, but it’s a big step forward with the new Real ID airport requirements — and keeps pace with Google Wallet’s own digital passports. More here.

• 🌙 Filoli Summer Nights | at Filoli | Woodside | 06/12 | More
  Twilight strolls, live acoustic sets & food-truck bites—every Wed & Thu 6-8 PM in the gardens.

• 🎬 Movies on the Square | at Courthouse Square | Redwood City | 06/12 | More
  Free double-feature: Despicable Me (6 PM) & Mean Girls (8:30 PM) outdoors!

• 🎶 Music in the Park | at Burton Park | San Carlos | 06/13 | More
  Friday-night concert series kicks off 6-8 PM—pack a picnic & groove with Mercy & the Heartbeats.

• 😈 Friday the 13th Whimsy Market | at Devil’s Canyon Brewing Co. | San Carlos | 06/13 | More
  Shop local artisans, sip craft brews & enjoy live vibes from 4 PM inside the brewery.

• 🛩️ Biggest Little Air Show | at Hiller Aviation Museum | San Carlos | 06/14 | More
  RC jets & stunt pilots light up the sky 10:30 AM–noon in this high-energy mini-airshow.

• 🏳️‍🌈 San Mateo Pride Parade | at 2nd Ave & B St | San Mateo | 06/14 | More
  March with the community at 10:30 AM as the parade winds to Central Park.

• 🛍️ HEAD WEST Market | at South B St (1st–3rd Ave) | San Mateo | 06/15 | More
  Browse 100+ local artisan and local business stalls along Downtown’s outdoor marketplace 11 AM–5 PM.

• 🎈 Kids’ Carnival | at Hiller Aviation Museum | San Carlos | 06/15 | More
  Hands-on cockpit tours, build-your-own gliders & other kid-friendly fun all afternoon.

• 🚗 Cars & Cabernet | at Auto Vino | San Carlos | 06/15 | More
  Vintage cars, local wines & gourmet bites converge for a Father’s Day showcase from 11:30 AM–2:30 PM.