Benny’s Tiramisu, Union Station’s Fall & Portland Events Guide

Start With the Tiramisu

The first time I tasted Benny’s, it wasn’t actually at Benny’s.

I was posted at the counter at Another Round, with a cortado, working on The Portland Logbook—half-writing, half-talking, which is usually how it comes together.

Emma, one of Benny’s sous-chefs, walked in with a vegan sub for Heather—the manager at Another Round and a good friend of mine—to try ahead of Benny’s opening. Heather tore it in half and slid me a piece.

I hesitated. Vegan subs rarely deliver. But this one? Crispy seitan, melty cheese, sesame roll still steaming. No weird aftertaste. It didn’t taste like a meat substitute, it tasted like something you'd go out of your way to eat again. And I will.

Then Nick walked in. Benny’s pastry chef. He handed Heather two quart containers of tiramisu like he was dropping off leftovers. Heather’s allergic to dairy—unlucky for them, lucky for me—so I got to bring it home. I was trying to be good, so I only took a few bites before bed. But then I woke up at 2 a.m., sat on my couch in the dark, pants nowhere in sight, and ate the entire container straight out of the quart. No regrets. It was boozy and rich and perfectly salted.

I’ve had a lot of tiramisu. It’s my go-to dessert whenever its on the menu. This one doesn’t just win; it mocks the others.

Watching Benny’s Take Shape

As mentioned, I write the Portland Logbook most days at Another Round. And Benny's... turns out it was opening right next door. I didn’t even notice at first, but Josh Sobel—the chef and owner—was always posted up a seat or two away.

I feel like I watched Benny’s take shape one interview at a time. Bartenders. Servers. Line cooks. All hired from the same table I was sending emails from. I wasn’t eavesdropping. Not really. I was just there. Over time, I saw Josh’s team growing, meeting quietly with the people who’d eventually run the place. You could feel it coming together in real time. One bartender. One cook. One server. The kind of crew that doesn’t happen by accident.

Then the space took shape. Josh brought in Mey & Co. the Portland design team behind Bread & Friends, Mr. Tuna, Ramona’s. Pros at making places feel like they’ve always been there. Benny’s fits the mold: warm, unfussy, and personal.

Woodhull handled the build.
Grace Rote lit the room with a soft glow that holds everything together.
Joe Watts developed the bar program, trained the staff, and laid out the bar
Three Left Hands Sign Makers painted every mirror, sign, and window by hand.
Family Bros did the Branding and Graphic Design

It’s a crew that knew exactly what they were doing. No flash, no overthinking—just people who built a place that feels good the second you walk in. Benny’s didn’t try too hard. It just got it right.

The Kind of Restaurant That Matters

Benny’s isn’t trying to be the next hot thing. It’s not gimmicky. There’s no Instagram wall. What it is, is thoughtful. Rooted. Built with intention from the ground up by people who give a damn.

In a city where restaurants open fast and close faster, where the next concept is already in the works before the current one has settled, Benny’s feels like a long game. Like something made to last.

I watched it happen, one table over. I feel like I ate my way through the edges of it before the front doors ever opened. And now that it’s here, it feels right. Like it’s been here all along.

The Hit List
Here’s what I’ll keep ordering until someone cuts me off:

Stuffed Peppers
Ramona’s Meatballs
Philly Cheese
Meatball Sub
Vegan Jawn
Cavatelli
Cannoli
Tiramisu (get your own quart, mine’s spoken for)

The Day Portland Tore Down Its Crown Jewel

The Station We Shouldn’t Have Lost

At the corner of Congress and St. John, there used to be a train station the size of a cathedral. Granite archways. A 200-foot clock tower that sliced the sky. You could hear its bell echoing across Portland, marking time for a city that doesn’t always keep it.

This was Union Station. And we bulldozed it for a strip mall.

The building was massive, Romanesque architecture, arched stone entryways, a 200-foot tower that marked the city skyline for decades. It connected Portland to Boston, Montreal, New York. You could board a train and be somewhere new by sundown. It made Portland feel like it belonged to something bigger.

Inside: wood benches, glass canopy ceilings, the kind of design that didn’t just serve a function—it made a statement. This was before travel was plastic and miserable. Back then, the journey still had style.

And then they knocked it down. Not because it was falling apart. Not because we didn’t use it. Just because we thought highways and parking lots were more important. Urban renewal, they called it. We traded one of the most beautiful public buildings in Maine for a place to park.

There’s a plaque now. The original bell sits a few blocks away in Congress Square Park, silent. Most people walk right past it. I thought it was a broken down elevator to a subterranean parking lot before I stopped to look at it.

We didn’t just lose a train station—we lost proof that public space can be built to impress. That a city should have an entrance worth showing off.

And now, after all that, we’re planning to build a new station right down the street. Different design, same reason. Because we finally remembered what we used to know: trains matter—and so does how we welcome people in.

📍Portland’s Union Station: Would You Bring It Back?

We traded one of the most beautiful public buildings in Maine for a place to park.

🐾 Adoptable Buddies of the Week! 🐾

🐈 Ellie – A long-haired beauty with diva energy. Shy at first, but once she trusts you? Biscuits, cheek rubs, and mouse toy marathons. Best for a quiet home with no kids and a patient heart.

🐕 Joker – 57 lbs of high-energy goofball. Loves games, jokes, and training time. Needs eye treatment, but he's all heart. Great with kids 8+, might be down for a chill dog buddy. Not cat-tested yet.

🐈 Wallace – 14 and fabulous. A sunbeam-chasing, pillow-sharing, forehead-kiss-loving gentleman. Loves face brushing and tunnel toys. Needs a mellow home (no kids or dogs), and someone willing to manage his ongoing medical care.

🐕 Interested? Check them out here