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By The Way
Detours with locals. Travel tips you can trust.
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A lobster roll, grilled cheese sandwich and fries at Highroller Lobster Co.
A lobster roll, grilled cheese sandwich and fries at Highroller Lobster Co.
CITY GUIDE

A local’s guide to Portland, Maine


A lobster roll, grilled cheese sandwich and fries at Highroller Lobster Co.
A lobster roll, grilled cheese sandwich and fries at Highroller Lobster Co.
  • By Kate Gardner
  • Photos by Sarah Rice
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Some may call it the “other Portland,” but to Mainers, this is the big city. With its highly regarded restaurants, abundant craft breweries, and world-class artists and writers, Portland is a hot spot of American creativity. And while the locals love these attractions, it’s the cozy feel and sense of community that truly make it home. Portlanders have their bartenders, their coffee shops and their booksellers, but they also love welcoming new people as much as they like seeing a familiar face.

There’s a reason every other person you talk to here will say they moved back after a decade away in Boston or New York. Portland has the vibe of a city while still being quintessentially Maine. So grab a beer and a lobster bib, and come see why this little hub is making so much noise.

Meet Kate Gardner

A New Hampshire native, Kate grew up camping in Maine most summers and always knew she’d one day make the rocky coast her home. Since moving to Portland in 2014, she’s worked as a reporter, mentored teen writers at the Telling Room and holed up in coffee shops to write her first novel.

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IN THE ACTION
Old Port
In the center of Portland’s peninsula sits the heart of the city: the Old Port. The wharves and cobblestone streets aren’t just throwbacks to the days of sea merchants; Portland is still very much a working waterfront. And with restaurants and shops packed along every small street, Old Port has no shortage of things to do. Name-brand hotels here provide ocean views, while lodging options on the edge of the neighborhood, such as the newspaper-themed Press Hotel, feature fun quirks. Find this neighborhood.
LOW-KEY
West End
One of the quietest places on the peninsula, Portland’s West End can feel like another world. The tree-lined streets are populated by brownstones and Victorian mansions, making them a haven for architecture buffs. Nestled among the historical beauty are quaint inns and bed-and-breakfasts (a couple are said to be haunted), as well as a number of Airbnb rentals. The neighborhood is home to highly rated restaurants, including the much-touted Tandem Coffee Roasters, and offers a view of the White Mountains from the Western Promenade. Find this neighborhood.
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Eat

BREAKFAST
Coffee Me Up
In addition to having possibly the smoothest nitro cold brew in town, this shop serves up some of the biggest, and best, breakfast sandwiches. They’re a struggle to get your mouth around, stacked high with egg, meat, cheese, greens, avocado and whatever else is on special that day. What’s more, most of them come with liptao, an incredible spread of mashed potato, roasted red peppers, feta cheese, chives and garlic. If you’re feeling something lighter, the croissants and fruit-filled pastries are flaky and delicious.
BTW: There’s seating out back on a small deck that’s hidden from sight. Go through the back door if it’s crowded inside.
221 Cumberland Ave., Portland, Maine 04101
BREAKFAST
Local 188
Portland has no shortage of quality brunch spots, but Local 188, with its Spanish-inspired dishes, is something unique. Located in the West End, the high-ceilinged lounge space is casual yet bold, with deep-red decor and funky art. The menu works well for picky eaters and adventure-seekers alike, boasting both your traditional eggs and home fries as well as a breakfast paella with bacon, eggs and mussels. If you find yourself somewhere in the middle, go for the mushroom-and-herb scramble, made with tangy goat cheese.
BTW: People don’t realize there’s a parking lot behind the restaurant. Head back there instead of struggling to find a spot on the street.
685 Congress St., Portland, Maine 04102
LUNCH
Sisters Gourmet Deli
Mainers love a good sandwich (the Italian was invented in Portland), and Sisters Gourmet Deli comes through with some of the best. There are over a dozen on the menu, each thin but packed tightly with fresh ingredients between the shop’s light-yet-doughy circular bread. A fan favorite is the Macintuscan — imagine a turkey club, but add apple slices and honey mustard. What the shop, located in Monument Square, lacks in size it makes up for with personality and color: It’s hard to miss its neon “Peace, Love, Sandwiches” sign from the window.
BTW: If sandwiches aren’t your thing, anything on the menu can be turned into a salad.
15 Monument Sq., Portland, Maine 04101
LUNCH
Bao Bao Dumpling House
Whether you’re looking for a light lunch or you’re full-on hangry, Bao Bao will satisfy. The snug West End spot is owned by a mother-daughter duo with an impressive résumé both in Maine and abroad. (Daughter Cara Stadler studied under Guy Savoy and Gordon Ramsay.) The dumplings, which are pan-fried or boiled, come six to a plate, so order a few different ones to share as a group. The menu also has hot and cold sections; the best from each are the sheng jian bao and the somen noodles, respectively.
BTW: The bulgogi beef dumplings come with their own creamy dipping sauce that will have you ordering a second round.
133 Spring St., Portland, Maine 04101
DINNER
The Highroller Lobster Co.
You can’t visit Portland and not eat lobster. While some people prefer to eat theirs by the water, Highroller is tucked away, making its back patio feel as if you’ve stumbled upon a secret. This seafood diner, which originated as a food cart, offers more than the typical lobster roll — try the lobster taco with the deep-fried cheese shell, or the lobster grilled cheese sandwich. If you’re looking for something truly unique, get the lobby pop and eat the Maine favorite on a stick.
BTW: To cool down, you can’t go wrong with the frosé. It’s a local hit.
104 Exchange St., Portland, Maine 04101
DINNER
Roma Cafe
While the 1880s-era mansion that houses Roma Cafe has been renovated many times over the years, walking inside still feels like walking into someone’s home. To the left of the foyer is a compact bar, and to the right is a cozy dining room. The candlelit atmosphere is warm and romantic, and the pasta is made fresh. You can’t go wrong ordering the rigatoni Bolognese.
BTW: If you’re looking to grab drinks before dinner or while you wait for a table, head downstairs to Bramhall. The basement bar has a wide selection of local beer and strong cocktails.
767 Congress St., Portland, Maine 04102
LATE-NIGHT
Arcadia National Bar
With a name inspired by Maine’s Acadia National Park, this arcade bar is a gamer’s paradise. Arcadia has pinball machines, old-school arcade games, Skee-Ball, board games, modern and vintage video-game consoles, and couches for non-gamers (or those in need of a rest from all of the above). The bar has a good selection of craft beer and cocktails, too — if you’re a fan of “The Office,” try the Bears, Beets, Battlestar Galactica. The comfort food is made to be paired with drinking, so get a grilled cheese or all-night breakfast sandwich and put your game face on.
BTW: If you want to bring kids, Arcadia is open to all ages from noon to 4 p.m. on Saturdays.
24 Preble St., Portland, Maine 04101
Temporarily closed
LATE-NIGHT
The Portland Zoo
This little place may not have any animals, but it is a great local watering hole. When the Zoo opened in Portland’s East Bayside neighborhood in fall 2018, it quickly became a favorite of those who prefer a more laid-back approach to a night out. The inside is small and intimate, while the larger backyard space, accented by cafe lights, has plenty of seating. Aside from the relaxed atmosphere, it’s the curated craft-beer selection that gives the Zoo its edge. With both local standouts and choice options from farther away, it’ll make you want to stay awhile.
BTW: Chat up your neighbors, especially if you’re sitting inside. The bar only seats eight, and unlike some zoo animals, Portlanders don’t bite.
41 Fox St., Portland, Maine 04101
(Matt W. Moore for The Washington Post)
LOCALS THINK YOU SHOULD KNOW
  1. Portland is all about buying local, so skip the national coffee chains and head to one of the city’s many charming independent shops. At Speckled Ax, you can request Fruity Pebbles milk in your drink.
  2. Parking is pretty terrible, and the garages and lots near the water will gouge you. Try to park farther up in the Old Port or in one of the other neighborhoods. The good news: Sunday street parking is free.
  3. Spend at least part of your visit off the peninsula. Take a ferry out to an island in Casco Bay or explore Woodfords Corner on your way to the breweries.
(Matt W. Moore for The Washington Post)

Do

Arts District
A few streets up the hill from the Old Port is Portland’s vibrant Arts District, home to the city’s art museum, the Maine College of Art, and numerous galleries and performance venues. There are also a number of restaurants and shops, including used bookstores, record stores and the Flea-for-All, an eclectic shop of vintage furniture and antiques. Along Congress Street, visit Congress Square Park, a compact urban space that hosts free movie screenings, live music and dance parties. At the other end, heading northeast, is Monument Square, where you can pop into the local library’s art gallery or grab lunch at the Public Market House.
BTW: Visit on the first Friday of the month for the city’s art walk, complete with street performers, free entrance to the Portland Museum of Art and local artists selling their work.
7 Congress Sq., Portland, Maine 04101
Industrial Way
Located off the peninsula, in Portland’s Riverton neighborhood, this craft brew park is a place that few find by accident. A whole day can be spent enjoying the park’s six breweries and one distillery, which are all mere feet apart and anchored by the behemoth Allagash Brewing Co. Each tasting room and its offerings are unique, as are the breweries’ outdoor spaces. Food trucks, meanwhile, rule the lunch and dinner scene, with options ranging from seafood classics to vegan junk food and Korean barbecue.
BTW: Foundation Brewing’s website maintains a Google Doc that discloses which food trucks will be in the park each day.
1 Industrial Way, Portland, Maine 04103
Print: A Bookstore
Maine is known for its stellar writers (any Stephen King fans here?), so of course Portland caters to all the book lovers out there. Print is one of the city’s newer bookstores, having opened near the base of Munjoy Hill in 2016, but it has quickly grown a devoted following. The light-filled space houses a wide selection of contemporary and classic fiction, as well as a bevy of nonfiction titles, on topics from social justice to cooking to sports. The store also hosts frequent author readings with local writers and nationally acclaimed novelists.
BTW: Print is co-owned by writer Josh Christie and Emily Russo, daughter of Pulitzer Prize-winning author Richard Russo, so there are lots of signed copies available.
273 Congress St., Portland, Maine 04101
Back Cove Trail
Portland has over 70 miles of walking trails, including the Back Cove Trail, just off the peninsula. The 3.6-mile loop wraps around the Back Cove, allowing you to walk, run or bike along the water. (Just be sure not to go at low tide, or it won’t be as scenic.) The trail also comes with stunning views of Portland’s skyline that aren’t visible from many other areas. If you head under Tukey’s Bridge on the trail, it connects to Bayside Trail, which leads to the grassy Eastern Promenade, where you’ll have sweeping views of Casco Bay.
BTW: You can start the trail from the entrance off Preble Street, across from the Hannaford supermarket.
295 Forest Ave., Portland, Maine 04101
Washington Avenue
This stretch in the East End has had a glow-up of late, becoming a destination for up-and-coming restaurants, including the low-key Tu Casa and the raved-about Cong Tu Bot. Walk from one end to the other and you’ll find a craft brewery, an oyster shop, a pottery cafe, a cheese shop and a kombucha brewery. You can have all three of your daily meals on this street and feel as if you’ve eaten like a king.
BTW: The best stretch of Washington Avenue is between Cumberland Avenue and Walnut Street, so stick within that area.
30 Washington Ave., Portland, Maine 04101
Shop vintage at Find
Portland has many vintage and secondhand clothing stores, and Find offers a strong mix of modern and throwback styles. The racks are stuffed to the max with offbeat T-shirts, denim jackets, patterned dresses and worn-in jeans, plus there’s a large selection of jewelry, sunglasses and other accessories. If you want to blend in with the Mainers, the shop sells flannels and the occasional L.L.Bean boots. Find caters to all genders and body sizes, and the stunningly low prices will have you walking out with bags full of cool, well, finds.
BTW: If you follow Find on Instagram, you can place holds on items they post about and pick them up in-store or have them shipped to you.
16 Free St., Portland, Maine 04101
Kate Gardner
A New Hampshire native, Kate grew up camping in Maine most summers and always knew she’d one day make the rocky coast her home. Since moving to Portland in 2014, she’s worked as a reporter, mentored teen writers at the Telling Room and holed up in coffee shops to write her first novel.
Sarah Rice
Sarah is a documentary photographer who’s lived in Portland for the past year. She moved to Maine from San Francisco because she’s obsessed with living by the ocean. The good food and creative people don’t hurt, either.

CITY GUIDES