I’m Jake Newman. The Portland Logbook is my love letter to this city: the food worth hunting down, the history that refuses to die, the corners you only find if you’re paying attention.

The Night Portland Moves Its Cars

Every winter, Portland does a dance.

We all move our cars at the same time and pretend we’re fine about it.

The alert hits and the math starts. Where did I park. How far am I willing to walk. Is that lot actually safe or just “safe if you squint and hope.”

Locals I’ve talked with all say the same thing. Everyone has a system. Everyone thinks their system works. Everyone has been wrong at least once.

By evening, the city shifts. Cars circling slower than usual. Headlights cutting across snowbanks that weren’t there yesterday. People scraping windshields with whatever’s closest. Credit cards. Old gift cards. Something that absolutely isn’t meant for ice.

Winter flattens us here. Renters and homeowners. People with garages and people who have never once lived somewhere with a garage. Everyone outside, bundled wrong, doing the same quiet choreography.

There’s always one car that doesn’t move. Still sitting there. Brave or doomed. Locals talk about it the next morning like a rumor. Did it survive. Did it get hauled off in the middle of the night. Was there a ticket folded under the wiper like a note left behind.

Last winter, it was the Harley on Park Street. Night after night it got buried by plow snow. Each morning it was still there, a little deeper, a little more questionable. Then one morning it was fully covered. No trace. I never saw it again.

You learn things on these nights. Which lots fill up first. Which streets always get plowed last. How far “it’s not that bad” actually is when it’s dark and the snow’s blowing sideways. You learn that winter here isn’t about snowfall totals. It’s about logistics.

By morning, everything looks rearranged. Streets wider. Snowbanks taller. Cars redistributed like someone half-finished a puzzle and walked away.

Your boots are drying by the door.
The street is clean.
And somewhere, another alert is already loading.

See Portland winter through a local’s lens

What Portland Actually Wants Right Now

A note for anyone putting events together in Portland.

We asked readers what actually gets them out the door. This isn’t trend-chasing or guesswork. It’s straight from people who show up, week after week.

Live music still leads. Small rooms. Familiar faces. The kind of nights where you plan on one set and stay for three. Portland wants a pulse, not a spectacle.

Food and drink came right after. Pop-ups, tastings, one-offs. Built around a table. No velvet ropes. No pretense. Just a reason to linger.

Right behind that was structure. Trivia nights, book clubs, run clubs. Clear start times. You know why you’re there. Tied with that, calm daytime things: yoga, talks, workshops. Proof that not everything has to happen at night or end late.

Family-friendly events matter too. Not for everyone, but deeply for the people who need them.

The common thread wasn’t hype. It was intention. People want a reason to go out that feels human, not exhausting.

If you host events here in Portland, this is your signal. Music, food, and low-pressure ways to show up and feel part of something. If you’re planning something that fits that lane, send it my way. I want to help people find it.

Here’s what people actually said they’d show up for this winter:

🟩🟩🟩🟩🟩🟩 🎶 Live music or performances (53)
🟨🟨🟨🟨🟨⬜️ 🍽️ Food or drink focused events (tastings, specials, collabs) (49)
🟨🟨🟨⬜️⬜️⬜️ 🧘 Low-key daytime events (yoga, talks, workshops) (34)
🟨⬜️⬜️⬜️⬜️⬜️ 🧒 Family or kid-friendly events (16)
🟨🟨🟨⬜️⬜️⬜️ 🎲 Social but structured events (trivia, book clubs, run clubs) (34)

186 Votes

THIS WEEKS CONDITIONS
☀️ SUNRISE: 7:15 AM
🌅 SUNSET: 4:13 PM.
🌊 SEA TEMP: 42.4 °F (Casco Bay,)
✨ Local Favorite Shop of the Week: The Artful Collector
✨ Local Artist of the Week: Jaden Kyung-Moon Bauch

Portside Real Estate Group

🏡 I write The Portland Logbook, and I also help people buy and sell homes in Portland.

If a move is on your mind, I’m always happy to help you think it through.

Work With Jake

🐾 Adoptable Buddies of the Week! 🐾

🐶 Pitch – 6 yrs
Big, handsome, and genuinely sweet. Pitch loves walks, a good game of fetch, and then settling in close on the couch. Smart, food-motivated, and eager to please. Best as the only pet. A great match if you want a loyal, steady companion.

🐱 Meka – 8 yrs
Quiet, gentle, and deeply affectionate once she feels safe. Meka loves sunbeams, brushing, and keeping close to her people on her own terms. She’ll thrive in a calm home with patience and care. Very special cat.

🐰 Snicket – 5 yrs
Shy at first, thoughtful always. Snicket needs time, space, and a calm setup to settle in. Give him room to roam and a little patience, and he’ll reward you with trust. Perfect for someone who likes to go slow and do it right.

🐕 Interested? Check them out here

If the link doesn’t open anymore, it means they’ve already been adopted!