A (Choose Your Own Adventure) Day in Portland, Maine


Portland’s Old Port

I first laid eyes on Portland nearly twenty years ago, and I’ve lived here for fifteen. It’s a marvelous place to call home—small enough that its rhythms quickly become familiar, but vibrant enough that I still don’t feel as if I’ve experienced all it has to offer. The greatest difficulty in sticking to this month’s A Day In… theme was narrowing my post down to only one day’s worth of activities, so I didn’t. (I did, however, restrict myself to staying within the city limits, even though that meant no lobster rolls at Fort Williams Park—one of my go-to options whenever entertaining out-of-towners.)


It’s no secret that Portland is something of a foodie destination. (Sidebar: can we retire the word “foodie”? It sounds ridiculous.) Just ask the Boston Globe. Or the New York Times. Or Travel + Leisure. Or Food & Wine. Hell, I once stopped into the Holy Donut and saw two separate TV crews shooting spots on either side of their tiny Old Port shop.

Mmm. Nosh.

Mmm, Nosh

I could write ten posts about my favorite places in Portland to eat, but I’ll do my best to exercise (a little) restraint. If you’re passing through, you could do worse than starting your day at the aforementioned Holy Donut, or Dutch’s, or Standard Baking. Feel like pizza? Slab or Otto is sure to please. A little peckish in the afternoon? Try Ten Ten Pié. Looking for a damn fine burger? Head to Nosh or Woodford F&B. If you like barbecue, the folks behind Terlingua sure know their way around a smoker. And if you wanna have a meal so tasty it’ll change your life, hit up Central Provisions or Miyake for dinner. Afterward, be sure to swing by Hunt & Alpine for a nightcap.

Of course, that’s just one man’s opinion, and it barely scratches the surface. If you want to dig deeper into the Portland food scene, Portland Food Map is an indispensable resource. I can’t recommend the site highly enough. I’ll probably weep when Anestes tires of running it.


I’m not gonna lie to you. This is where the one-day thing gets dicey. If you wanna check out Portland’s booze scene, don’t be a hero. Prioritize. Designate a driver or take the Brew Bus. And for god’s sake, hydrate.

Free Flight Courtesy of Allagash

A free flight courtesy of Allagash

For my money, the best place to start is Industrial Way, off Riverside, where the venerable and munificent Allagash offers free flights and a spectacular tour (the latter is also free, but requires you to sign up online). Across the road from Allagash, Foundation and Austin Street are quietly brewing up some of the tastiest beer on the planet. Alas, Bissell Brothers used to be there too, but they recently moved to a snazzy new brewery on Thompson’s Point that’s more than worth the trip if you, like me, love hops… and Cellardoor Winery is right next door.

East Bayside offers you some good bang for your booze buck, with loads of options within walking distance. Rising Tide and Bunker are my favorites of the breweries. Urban Farm Fermentory makes tasty cider and kombucha. Maine Craft Distilling pours free samples of its spirits, including a shockingly good malt whiskey and a blueberry moonshine for those who like their hooch a little sweeter. And just up the hill on Washington, Oxbow and Maine Mead Works are worth a stop.


Seems to me, you’ve gotta walk off all that food and booze. To that end, here are a few suggestions.

Like museums? Whether your taste runs from fine art to cryptozoology, Portland’s got you covered. Plays? Check out Portland Stage (I’m writing this post on Saturday, and I’ve got tickets to see Heathers there tonight). We’ve got no shortage of good music coming through (I’m particularly psyched to see Julien Baker next week). And I’ve already written at length about my love for Portland Architectural Salvage.

Jewell Falls

Jewell Falls

Maybe you’d prefer something a little more outdoorsy? You could wander the Old Port (where I put Lester’s fictitious bar) or the Back Cove. Explore the islands of Casco Bay by ferry—or better yet, by kayak. You may know Portland is crisscrossed by countless nature trails, but did you know it also has its own waterfall? Until recently, I didn’t.

Portland’s got loads to offer book nerds, too. A spectacular public library. Three great indie bookstores—LetterpressLongfellow, and Sherman’s—with another on the way. (If you stop into any of them, might I recommend you pick up a copy of THE KILLING KIND? Most hardcovers in town are already signed. The paperback comes out 8/2.) And I almost hesitate to mention it because it’s something of a secret, but one of my favorite hidden spots in town is the garden tucked behind Henry Wadsworth Longfellow’s house on Congress Street.


Yes, those are typewriters.

Yes, those are typewriters

Portland’s got loads of nice hotels, but since I make my living peddling words, I wanted to highlight one in particular: The Press Hotel. Once the headquarters of the Portland Press Herald, it’s since been reborn as every writer’s ideal home away from home.

Of course, you could just move here to save yourself the trouble of finding a hotel. Lord knows it’s one of the best decisions I’ve ever made.


Chris Holm is the author of the Collector trilogy, which blends crime and fantasy, and the Michael Hendricks thrillers. His first Hendricks novel, THE KILLING KIND, was nominated for an Anthony, a Barry, a Lefty, and a Macavity Award and named a New York Times Editors’ Choice, a Boston Globe Best Book of 2015, and Strand Magazine’s #1 Book of 2015. Hendricks returns September 13th in RED RIGHT HAND.

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9 Responses to A (Choose Your Own Adventure) Day in Portland, Maine

  1. Thanks to this roundup we’re going to be overrun by even more tourists, but if they’re crime-writing fans, that will be a very good thing.

    He’s right folks. You’ll never run out of places to eat, good local beer to drink and things to do in Portland. It’s a gem in all four seasons and the people are friendly and entertaining, too!

  2. Barb Ross says:

    A wonderful list! Ticking off the things I’ve done, and adding the others to my “To Do in Portland” list.

  3. Richard Cass says:

    Nice collection, Chris! BTW, hydration points include Portland Public Library and (dogs only) Arabica, now Crema II or something on Free Street. Still waiting for the Portland Public Restroom Directory, though . . .

  4. Peter Murray says:

    Thanks Dick. I’ve got to get out more. But I did find the waterfall about a year back. Great glimpse of Portland.

  5. Chris, don’t worry, I plan to continue publishing Portland Food Map for a long time to come. That said, after 9 years it would be nice to have a week of vacation. Want to volunteer?


  6. Pingback: The Busy Season | Maine Crime Writers

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