A music lover’s guide to Portland, Maine

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Portland is an old town with good bones. It’s a place of four true seasons, with hot summers and freezing winters. The cold filters people out of Maine: if you can’t handle it, you leave. The town has become much more cosmopolitan in recent decades – they say it has the most restaurants per capita in the US – but it still has the attitude of a working port. I grew up just outside the city, in a place called Falmouth, one of those names borrowed from Cornwall. I’ve travelled a lot but always knew I wanted to raise my kids here. There’s a classic approach to life in Portland; we’re a little bit out of time – and happier for it. 

Portland’s music scene has definitely influenced my work at Bandcamp, an online record store where fans can buy music and merch directly from artists. It’s different from a big scene like London or New York. You know the artists and they know you, which is really what Bandcamp is about. 

I’ve done a bit of touring myself, having moved from Chicago, where I studied, to Atlanta to play with a band called DPOM (Dirty Painters of Maine) in 2003. We were old friends from Portland and paid our way by painting houses. I learned what it’s like to try to pay your bills with music – partly that it’s not for me! – but that’s why I feel so passionate about offering a scaffold to help great artists to emerge.

Winter or summer, I start my days at Speckled Ax on Congress Street, a small coffee shop that also brews tea from around the world. I have a Chinese black tea and then a cup of green tea at midday. My office is nearby and it’s also where the Portland Museum of Art and the State Theatre are.

The State Theatre, a classic, almost 2,000-capacity building that used to be a movie house, was a big deal for me as a kid. At the time, Portland was not a place where many big acts played – it was the end of the line. So when a big name was here, it was an event. I saw so many special shows – all of them formative experiences – including classic acts such as Bob Dylan, John Scofield and Funkadelic. 

Here, it’s often fastest to get somewhere by boat

My first port of call for consistently fresh sushi is Mr Tuna. There’s a robust Japanese ethos here because of the outstanding seafood. A more classic spot is Scales, which has been around forever and does everything, all perfectly prepared. I’ll have the seafood stew or just ask, “What’s fresh?”

I’m also a sucker for a lobster roll. The regional debate is mayo versus butter, Maine versus Connecticut. Truthfully, it just comes down to the quality of the lobster: if it’s fresh, cooked right and there’s enough of it, you don’t need much else. Erica’s, a shack about an hour away at the end of the Harpswell peninsula, does a “crabster” roll (local crab and lobster) that was the most delicious thing I ate this year.

In Casco Bay, where Portland is, you’ll find the Calendar Islands – Calendar because there’s one for every day of the year. With all the islands, Maine has more miles of tidal coastline than California or Texas. That means it’s often fastest to get somewhere by boat. 

I don’t own a boat but I kayak a lot. I like being human-powered. I’ll often paddle towards Chebeague or take my kids to Littlejohn Island on their bikes. You head over two bridges and there’s a nature reserve on the island’s tip. There are no cars so you can just enjoy the birds. Be warned: swimming is cold, even in summer. The Gulf Stream bounces off Cape Cod so we don’t get any of that warmth.

Back in town, record shopping is a must. Enterprise Records has been around forever and only sells vinyl in mint condition. The owner, Bob, is an old-school guru type: slightly cranky, but he knows everything about music. (He has his own grading system that he’ll have to explain to you.) Moody Lords is newer but also a good shop. The last record I bought there was Wayne Siegel’s Autumn Resonance. 

For a gig, I might head to Space, a non-profit arts venue that always has interesting shows and exhibitions – jazz, world music, indie rock. Another great club is Blue Portland Maine, which is really the only venue in the area that focuses on jazz and has that small “tiny tables” feel. You might catch Dave Gutter, a Portland artist I’ve been following for a long time. He encapsulates the Portland scene: incredible songwriter, incredible producer and has been bringing up local artists for years. Portland recently passed a moratorium to stop Live Nation opening a big venue, which says all you need to know about the music here.

Coming back to Portland after travelling always feels like stepping into a sea of peace. There’s no big city bustle. I don’t remember the last time I was in a traffic jam. The people are quiet and determined but they know how to enjoy their lives. As long as you can shovel snow and deal with the ice, it’s a pretty special place to be. Portland is self-selecting in that way – you have to love all of it to be here, and I really do.