One Thing to Make Them Fall in Love with Portland

Portland is a city that reveals itself in moments. Not the Instagram slideshows, but the flashes you only catch when you live here: the sharp salt air on the Casco Bay ferry as it pulls into Peaks Island, the smell of woodsmoke drifting from Fore Street, the last streak of sunset from the top of Fort Sumner Park. The good shit. The stuff that feels like yours.

I’m working on something for the Logbook, and I want to know: what’s one thing, an experience, a place, a bite, a ritual, you’d share to make someone feel like a local here? Not the obvious stuff. The moment you’d give to someone you love so they could fall in love with the city we call home. To kick it off, I asked the author of The Portland Dirt to share theirs.

Now don’t worry, your answer doesn’t need to be as poetic or as beautiful of an answer, but that’s just who G is.

❝

“Come on everyone, we’re using our voices for good tonight!”

On Wednesdays, we go to the Jewel Box. We run in packs to the pink bar we love to find the karaoke list open for us. The night cools like August nights are supposed to. Shimmering curtains set the scene, dried flowers up in the rafters and around the disco ball, the most creative cocktail menu in the city. An honorary queer bar, more ethereal than the rest. The bartenders are friends, they know that obscure song you want to sing. Everyone echoes the reprise, “Thank you for coming!” “Thank you for being here!”

The list opens at 9PM and everyone is a celebrity sighting. There are some songs you can’t get away from at karaoke, but at the Jewel Box your options are as unlimited as YouTube - projected on the painted wall behind the bar. First come, first serve, and a bar of good company singing along, whether you’re tucked in by the windows, claiming a spot at the bar, or overseeing it all in the loft. I’ve been moved to tears, here, and uplifted high above the city with friends over every shoulder. We share a mic, we share a life, we are singing & spinning in the tight corners between the bar and the tables, between antique glasses and bowls of lost earrings. Hope glows bright in the West End. In Portland, the middle of the week is as exciting as the weekends, maybe even more so. Bring cash, I’ll meet you there.

That’s their Portland. Now I want yours.

Maybe it’s sitting on the Eastern Prom at sunset, gelato in one hand and coffee in the other. Maybe it’s waiting in line at Little Tandem on a Sunday morning, watching the whole city pass by. Maybe it’s picking blueberries until your hands stain purple, then baking something you’ll eat on the stoop.

It can be anywhere in Greater Portland. Just send me yours: the single, small, unforgettable thing that would make someone fall in love with the place we call home. I’m collecting them to share.

Click the link below to tell me!

Survey: The One Thing

Portland’s Original Group Chat

On Munjoy Hill, where the wind cuts in from the bay and gulls scream over the rooftops, there’s an octagonal tower that’s been watching this city longer than anyone alive. The Portland Observatory. Built in 1807, back when ships, not smartphones, were the lifeline.

It wasn’t built for tourists. It was the city’s early warning system. A man with a telescope scanned the horizon for sails, then ran flags up the mast to tell the wharves who was coming in. Merchants got hours of notice to get their crews ready. News traveled from hill to harbor faster than a horse could manage.

During the War of 1812, it doubled as a lookout for more dangerous arrivals. Not every set of sails was friendly.

These days it stands there quietly, paint peeling in places, wood breathing in the salt air, while joggers pass without looking up. But it is still the same tower, still keeping its watch over Casco Bay, holding the city’s first real conversation with the outside world.

If you want to see Portland the way it saw itself two hundred years ago, climb to the top on a windy day. Look east until your eyes water. That is the view everyone was waiting on.

Go visit the Portland Observatory

🐾 Adoptable Buddies of the Week! 🐾

🐕 Sweetheart – 4 years, 66 lbs
Shy, cautious, and learning the ropes. Needs a patient, cat-free home (no kids under 8). Warms up to be soft, sweet, and quietly affectionate.

🦴 Gus – 5 years, 103 lbs
Gentle giant with a goofy streak. Great with laid-back dogs and kids, but no cats or critters. Mellow, loyal, and happy to lounge with you.

🐾 Tundra – 8 years, 75 lbs
Big-hearted solo star who wants all your attention. No other pets, kids 10+. Goofy, sweet, and ready for couch cuddles and adventures.

🐕 Interested? Check them out here