Kitchn’s Bite-Sized Guide to Portland, Maine

updated Jun 3, 2019
We independently select these products—if you buy from one of our links, we may earn a commission. All prices were accurate at the time of publishing.
Post Image
Credit: Erin Little

In the sixth installment of our Bite-Sized Guide series, we’re heading to the small coastal city of Portland, Maine. Yes, Portland, Maine. The small New England city has become known for its booming food and drink scene, on par with larger cities. The last decade has seen chefs and brewers opening restaurants and breweries in droves. The awards and accolades continue unabated — and people are taking notice.

(Image credit: Erin Little)
(Image credit: Erin Little)

Why Portland Is the Best Small City for Food-Lovers

Portland is one of many small U.S. cities experiencing a reimagining of American dining, and it’s perfectly positioned for this renaissance, both geographically and culturally.

Because the city is compact — the heart of downtown, located on a peninsula, is only two miles wide — Maine didn’t experience the suburban sprawl of other New England states, meaning the farms for that farm-to-table dining are only a few miles away from restaurants downtown. That Portland is located right on the ocean means there’s access to some of the world’s best seafood, from the famed lobster to sea scallops, uni, and oysters.

(Image credit: Erin Little)

The connections here are easy to make, from chefs sharing tips on who forages mushrooms to brewers working with farms to source Maine-grown hops and grains. You’ll notice it, too: While sipping a cocktail at happy hour, the bartender will recommend a restaurant for dinner, and when you get to that restaurant, your server will happily suggest a great spot to grab breakfast tomorrow. You’d be hard-pressed to find another city where its locals are as enthusiastic and supportive as Portland’s.

(Image credit: Erin Little)

The Food of Portland, Maine

When I moved here in 2008, I had no idea Portland had such a thriving restaurant scene. I started a food blog, The Blueberry Files, to document my exploration of the city’s food scene (primarily for my family, living “from away” as Mainers call anything out-of-state). Nine years later, it’s all I can do to keep up with all of the new restaurant and brewery openings.

While you can find the requisite fried seafood and soft-serve ice cream of other coastal towns, you’re more likely to indulge in a plate of fried cauliflower and chickpeas or a wild blueberry milkshake in Portland.

(Image credit: Erin Little)

The Best Time to Go to Portland, Maine

Have we convinced you to visit? Lucky for you, now is the best time to visit Portland. Maine’s cold, harsh winter is nothing but a distant memory come July and August. Whether you want to explore the whole city on foot, take a ferry to nearby Peaks Island, enjoy your brown butter lobster roll al fresco, catch a movie on the rooftop of a bowling alley, or check out the Saturday Portland Farmers Market in Deering Oaks Park, summer is the dreamiest time to visit.

It’s also the busiest, meaning you’ll experience the longest waits to get into popular restaurants (seriously, we’ve heard of two-hour-plus waits for a table at Duckfat and Eventide) and the highest prices for lodging. If you’re looking further ahead, fall is a nice time to visit, as families with kids head back to school, and the days are still warm. Spring can be a bit iffy weather-wise, but if you get a nice stretch, you’ll have all the perks of summer without the crowds.

Portland is a year-round destination with plenty to do no matter the season, meaning businesses don’t close in the off-season. There’s usually plenty of snow on the ground December through March, and even April snowstorms are not unheard of, making travel tenuous. Winter visits usually mean diminished crowds, although as the word continues to spread about Portland, this is increasingly less true, especially in popular breweries’ tasting rooms.

(Image credit: Erin Little)

Portland, Maine by Neighborhood

Portland is a small city of 65,000 people, and its downtown area is located on a peninsula framed by the Fore River and Casco Bay. Most of the food and drink spots you’ll be looking to visit are on the peninsula, save a few breweries easily accessible by Uber or Lyft. Portland neighborhoods are small, only a few square blocks each, as the whole peninsula is only two miles from end to end.

East End/Munjoy Hill

This neighborhood is marked by Munjoy Hill, its apex the highest point on the peninsula, and the Eastern Prom, a sweeping green space with fantastic views of the islands of Casco Bay. The East End is mostly residential and prime for an Airbnb stay with coffee shops, boutiques, and its proximity to downtown. Congress Street, the main artery of the city, runs up Munjoy Hill, with most of the businesses along it at the base and top of the hill.

(Image credit: Erin Little)
(Image credit: Erin Little)

West End

Portland’s West End was where wealthy merchants and ship captains lived, so you’ll find a concentration of historic homes and scenic streets here. The heart of the West End is the intersection of Brackett and Pine Streets, where you’ll find restaurants, markets, and cafes. Longfellow Square marks the Eastern border of the West End and is another hot spot for bars and restaurants.

Arts District

So named for the galleries that line Congress Street and the Portland Art Museum, the Arts District also contains restaurants, boutiques, and thrift shops. The monthly First Friday Art Walk happens here, and the area is home to many of Portland’s music venues like The State Theater and Port City Music Hall.

(Image credit: Erin Little)
(Image credit: Erin Little)

Old Port

The commercial heart of Portland, this district is Portland’s busiest with shops, restaurants, bars, and plenty of tourists. Commercial Street runs along the waterfront with piers extending into the harbor. Some contain shops and markets, while others are private for commercial purposes. Definitely visit the Old Port during your stay, but also venture further afield for a taste of how the locals live.

(Image credit: Erin Little)

East Bayside

On the back side of the peninsula and bordered by the highway, this neighborhood was recently home to industrial businesses and light manufacturing. After a few breweries and artist studios opened up, however, the area attracted other drink-related businesses, making it a great place to spend an afternoon. You can easily walk to the tasting rooms of several breweries, a distillery, a coffee shop, and even a “fermentory,” a kombucha, cider, and beer brewery.

Getting There & Staying There

With the regally named Portland International Jetport (airport code: PWM) located 15 minutes from the city center, flying into Portland is a great option. Concord Coach Lines and Amtrak Downeaster both offer service from Boston to Portland’s Transportation Center. A car is not necessary, as much of downtown Portland is walkable, with cabs, Uber, and Lyft available to take you to any off-peninsula destination. Portland’s Old Port can be very congested with traffic and pedestrians in peak summer months, and parking can be hard to find. Street parking is metered six days a week, excluding Sundays, from 9 a.m. until 6 p.m.

(Image credit: Erin Little)

Downtown Portland has an increasing number of hotels, but the rooms will come at a premium on prime weekends. If you’re traveling by car, hotels in South Portland or by the airport are a short drive from downtown Portland, and many offer a free shuttle to the Old Port. Those looking for a boutique experience should check out The Press Hotel downtown, the West End’s Pomegranate Inn, and The Mercury Inn in Parkside. Airbnb offerings grow every season, with options on the peninsula the best for those looking to walk everywhere.

Read More About Portland, Maine:

(Image credit: Kate McCarty)

About me: I blog about Maine food at The Blueberry Files and have written food and drink features for several alt-weeklies and magazines. I teach food preservation at the University of Maine Cooperative Extension. I am the co-founder of the Portland Spirits Society, a women’s whiskey appreciation club, and also the author of two books, Distilled in Maine: A History of Libations, Temperance & Craft Spirits and Portland Food: The Culinary Capital of Maine.