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Situated in the historic West End—what some consider to be Portland’s prettiest area—this red-brick, Federal-style mansion has housed a Prohibition-era hideout, a boarding school and, for the past two decades, the intimate Danforth Inn. Today, its nine rooms are uniquely furnished with a mix of contemporary European pieces and Asian influences, as well as nearly a million dollars’ worth of modern art.


A small garden blooms with lilacs, fragrant herbs, and edible flowers in the spring and summer, while 13 working fireplaces—there’s one in each room and two in the West End Suite—make for cozy evenings come fall and winter. After a renovation completed in 2015, Tempo Dulu, a 36-seat Southeast Asian restaurant, opened with dishes like grilled lobster with spring onion cake, and dramatic design details such as a live-moss chandelier.


In 2017, the inn expanded on the Asian theme with its Opium bar; decor is meant to evoke a 1920s Shanghai speakeasy, and cocktails include the Danforth Swizzle, a rum-based drink accented with Chinese five spice–infused bitters.

Right around the corner from Powell’s Bookstore and Sizzle Pie, the vibe here is fantastic. The walls are kind of spartan, there’s a record player in the corner, and you can roam on free Internet to your heart’s content. These guys definitely know the food scene here and have great tips. My iced chai latte? Served in a mason jar. Yum and Yum. And those caneles, pictured? They were featured in Portland Monthly. I believe Courier is following the ice cube trend with one big block of ice in either a square or rectangle. I also love the everyday musings on their blog.

Situated on Northeast Portland’s Alberta Street, smack in the middle of the Alberta Arts District, Caravan is an unique alternative to the same old hotels or vacation rentals. The hotel is comprised of six tiny, individually styled houses for rent, from the cabin-like Skyline (made mostly from upcycled material) to the Amazing Mysterium (a vaguely steampunk affair modeled after a vardo gypsy wagon, with lovely additions such as stained-glass windows and lots of built-in shelving). In true Portland style, the houses are clustered together in a “pod,” similar to how many of the city’s famous food carts are arranged. In lieu of a lobby, there’s a central outdoor common area with a fire pit (s’more-making is encouraged, and supplies are provided). Note that live bands perform for guests and a limited number of community members on Wednesday evenings during the summer months, and the whole area gets busy on the first Thursday of every month, when Alberta Street transforms into a pedestrian-only night market-cum-street party that lasts well into the evening.

Rising from the ashes of the 60’s Red Lion Hotel is the east side’s latest entry into Portland’s hip hotel scene—the Eastlund. Cut from the same pedigree as the downtown Modera Hotel, the Eastlund is a welcome upgrade in the evolving convention center area. The fun starts in the bright, expansive lobby, where eye-catching art welcomes visitors. The staff is tuned to deliver exceptional customer service, and the vibe is genuine and unpretentious. Amenities include great food, local spirits, tech-savvy rooms, and super-fast Wi-Fi throughout the property.

The rooms and public spaces put art front and center, while the meeting areas are wired for productivity. Business and leisure travelers also benefit from attention to detail and a staff committed to getting it if it’s not already available. The efficient, comfort-forward rooms boast big flat-screens and colorful décor, and the river and city views from the upper levels are spectacular day and night. An easy MAX ride from the airport, The Eastlund is also delightfully located within walking distance of a variety of transportation, entertainment, meeting, and dining opportunities. With so many on-site amenities, however, you might just find yourself pleasantly planted during your Portland stay.

This is one of the new hot bars, just a few blocks down from the Jupiter Hotel on SE Grand and Morrision. Checkpoints: skinny hot bartenders in wifebeaters who shake up some inventive cocktails, a DJ, a 110-year old piano, a horseshoe bar and an impressive late night menu (cuban sandwiches, anyone?). I had the Sam Issacs which was mentioned in Portland Monthly as the drink to have but not even on their menu. It has bourbon, mint, blackberries and lime. It’s DELICIOUS. Portland seems to have a thing for libations with ginger beer and I’m loving it. I followed up with 96 Tears, a combination of vodka, lime, ginger and ginger beer. This was light but boozy. The perfect way to start a night or in this case, I’d end it here if you want to dance.

Anyone taking diligent notes on Portland decor is sure to notice similarities in design from location to location beyond a love for taxidermy. Much of that Rose City decorating style emanates from Schoolhouse Electric. Located in a 115-year-old redbrick warehouse and factory building in an industrial part of the city’s West Side, Schoolhouse Electric sells everything from perfect reproductions of 1960s-era IBM clocks to more vintage sconces and analogue clocks than you can shake a stick at. The store’s Ristretto Roasters coffee bar provides a caffeine boost when your energy for curated doorknobs reaches its limit.

Housed in a converted elementary school dating back to 1915, this sprawling hotel complex has long drawn out-of-towners and local Portlanders alike with its bars, restaurants, miniature movie theater, and even a heated soaking pool that’s open to the public for a small fee. While these amenities—along with the hotel’s sprawling school grounds and proximity to the popular Alberta Arts District—are enough to make it one of the most attractive spots to stay in town, its real cred shines through in the 57 guest rooms, many of which are actually converted classrooms (and still have some of the original scholastic features, such as chalkboards, integrated into the room design). Don’t leave without sampling some of the McMenamins signature brews in the Boiler Room Bar, housed in what was once the school’s boiler room.

When it comes to pub crawling in Portland, Deschutes Brewing is a classy stop to regroup and recharge in the Pearl. With more than a dozen taps pouring the usual suspects along with a collection of seasonal and experimental brews made specifically for Northwest tastes, the bar has something for every beer lover. The kitchen serves fresh, sustainable fare, including vegetarian and gluten-friendly options. Try the beer-battered halibut or the smoked brisket. The steamed clams with a side of sweet potato fries will also keep you going until your next destination.

Local is the operative word in the Portland, Maine food scene. Ask a waiter what Atlantic Day-Boat halibut is exactly, and he’ll spin a story about the local captain who pulls in with the day’s catch. At the height of summer, it seems that every ingredient is caught, raised, foraged, or grown in the vicinity. So it’s no surprise that Maine oysters take pride of place at Eventide Oyster Co. Sure, there are some bivalves from New York and the West Coast, but my advice is to quiz the waitress about the ones from West Bath, Casco Bay, and the Damariscotta River. A hit of frozen Tabasco came on the house, but these plump beauties are best with just a squeeze of lemon.

There certainly are other ways to while away a summer day in Greater Portland, but you’d be hard-pressed to find a better experience than island-hopping aboard a Casco Bay Lines ferry. Sure, you can simply ride out to an island for a look-about and return, or enjoy a sunrise, sunset, or moonlight cruise. But for a real immersion, consider the Mailboat Run. You’ll be among islanders, visitors, pets, and freight to-ing and fro-ing between Little Diamond, Great Diamond, Long, Cliff, and Chebeague islands. The 2½-to-3½-hour working cruise is offered twice daily year-round; bring your own picnic lunch on the morning run or snacks for the afternoon one.

Doughnuts are to Portland what coffee is to David Lynch, both essential fuel and calling card. While there are many pretenders to the title of the city’s best doughnuts—Voodoo Doughnuts certainly sells the most Instagrammable food products—Blue Star, from ubiquitous local restaurateur Micah Camden, is the most consistent. Flavors range from powdered sugar to maple bacon to passion fruit cocoa nibs, sold fresh daily until no more remain. The downtown location gets crowded early on weekends, so plan ahead. In a pinch, grab them at Blue Star’s airport location—which makes asking a friend to pick you up at the airport a sweet request indeed.

I was on a cruise in Italy when I heard about this place. I’d mentioned that I was heading to Portland, and a fellow cruiser, a native of the town, had told me that if they had one recommendation it would be the ice cream at Salt and Straw.

What she didn’t tell me was that the flavors are not your usual vanilla, chocolate, and raspberry ripple. In fact, the first thing I tasted at Salt and Straw was their new “Bollywood” recipe, which included carrot custard and cardamom, which sounds almost sensible when you considered that some of their most popular flavors include prosciutto and goat cheese.

There was a huge line, even on a Friday mid-afternoon, but it was worth it for the almond brittle with salted ganache, not to mention the apple pie with real chunks of cheddar cheese. They’re doing their best to “Keep Portland Weird” here...and it tastes good.

When the Last Bookstore debuted in 2005, the name was meant to be ironic. Now, in a world of Kindles and iPads, digital books (or at least digital bookstores) are the norm, and brick-and-mortar establishments such as the Last Bookstore are a dying breed. That hasn’t stopped this Downtown L.A. icon from growing. The shop still buys, sells, and trades new and used books and vinyl records just as it did when its doors first opened over a decade ago, and it shows no signs of stopping anytime soon. Come in to browse the store’s impressive collection, to hang out for an afternoon, or to catch author talks and more. The Last Bookstore puts on some killer events, and past speakers have included the cast of Portlandia, How to Kill a City author Peter Moskowitz, and Holocaust survivors. Oh, and they occasionally give away free concert tickets on their Instagram account, so it’s worth a follow even if you’re not a die-hard bookworm.

The Tin Shed is probably nowhere near wherever you might be in Portland but that matters not. Get a cab and go over there because the biscuits are so good they’ll make you wanna slap yo mama! You serve yourself coffee while you wait under the covered patio seating, they welcome dogs and their bloody mary is spectacular. This place rocks. Go check it out.

I wouldn’t normally visit a hotel restaurant just for the purpose of having a sandwich. But this is the second restaurant by Vitaly Paley, one of Portland‘s most beloved chefs, and I’d been told it was a good place for lunch. I hadn’t guessed that most of the menu would be sandwiches, and I have to admit to feeling a little disappointment when I saw it. I shouldn’t have. The dungeness crab reuben was a flaky fish marvel, while the heirloom tomato salad I had with it was a perfectly pert accompaniment. The homemade cream soda, meanwhile, was as sweet and delicious as anything in an Enid Blyton novel, and it had me suppressing the urge to exclaim “How jolly!” Anyway. That’s just me. If you like a sandwich, I think you’ll probably like these.