72 hours in Portland, ME

How to enjoy one of the top two Portlands in America

The New York Times has a great travel section called “36 Hours in…”. But why only 36 hours? Why not spend a whole 72 hours in a place? I was left contemplating this quandary when car trouble turned a two-night stay in Portland, ME into a longer stop.

My misfortune is your gain, dear reader, as I address the age-old question: What if a visitor spent an entire 72 hours in one place? In the case of Portland, the answer is: pretty good. The more detailed answer, below, maps out how to spend three very productive days eating, drinking and sightseeing your way through Portland.

Hack! To get the inside scoop, check out where the locals eat.

Portland is not an undiscovered gem. It’s a popular place to visit, and plenty crowded during the summer. But if you are traveling from overseas, or are from outside the northeast, it’s not an obvious stop, but one worth making.

Fun fact: Maine is bigger than you think. In fact, it’s inlet-strewn coast is longer than California’s. So there is a lot to see beyond Portland.

Day 1: Nautical adventures

Breakfast: Order ahead at the Standard Baking Company (to avoid the line). Their baguette is remarkably good, and plenty of amazing pastries as well.

Portland’s harbor is very much a working one, with the sights — and smells — to match. The harbor front provides a natural geographical anchor to the city, with commercial shopping and restaurants surrounding it. If you have a hankering for Chowder, Gilbert’s Chowder House by the harbor is a local institution.

You can buy fish right on the harbor in the aptly named Harbor Fish Market.

If you want something a little less traditional, Central Provisions offers small plates characterized by a mix of bold flavors. Struggling to recall another meal where I had as many close-your-eyes-and-savor-the-flavor moments. Its a small space, so reservations are key.

Central Provisions

Activity: Sail the not-so-high seas

There are lots of ways to explore Casco Bay, which surrounds Portland, including ferries (see more below), sea kayaks, and water taxis. But let’s face it, how often do you get a chance to spend a couple of hours on a sailboat? There are plenty of options that allow you to hop on during the day or for an evening sail. They are typically BYOB, so we also brought some seafood and a bottle of wine on board to make it a dinner cruise. Even if it seems warm on land, be sure to bring a sweater because it can get quite cool on the water.

Having managed the not-so-high seas, you can reward yourself with a nautically themed cocktail at Blyth and Burrows. Going to a cocktail bar means, for me at least, trying something I would never pull off at home. Hence, the choice of the Ship Captain Crew which is made up of (checks notes) dandelion bourbon, rhum (which, it turns out, is a meaningful distinction from plain old rum), Montenegro, amontillado, lemongrass, spruce tip, and pecan wood smoke. So yes, will not be replicating this at home, no matter how delicious it was.

If you want to invest in the cocktail scene in Portland, here is a longer guide.

DAY 2: Beer and BBQ

Breakfast: The local farmers market runs on both Wednesday and Saturday mornings at Deering Oaks Park. You should buy fresh blueberries at least once while in Maine, and if they are in season, this is the place to do it.

Portlanders are serious about their coffee, and locals vary on which is the one worth waiting in line for. A few blocks from the farmers market you can find Tandem Coffee + Bakery, which offered up a peach pie with a Mezcal flavor that I won’t forget anytime soon.

Activity: Micro-brew tour

There are lots of micro-breweries in and around Portland. Unless you have a designated driver, the smart play is to find a neighborhood with a fair cluster of them. This gives you an excuse to visit the East End. We stopped at Belleflower Brewing, Lone Pine Brewing, Goodfire Brewing and Austin Street Brewing, but could have easily tagged on a few more without leaving the three block radius in the Fox/Anderson Street area that is a short walk from downtown (and if you need a pick-me-up, there is another Tandem coffee location on Anderson St).

Oxbow specializes in farmhouse ales of all kinds, including some funky mixed fermentation options. It also offers Duckfat Frites Shack, which serves, well, duckfat frites. The main Duckfat restaurant is a battle to get into, so this gives you a much more accessible option in a lovely location.

Across from Oxbow is the the truly excellent Terlingua for barbecue. The BBQ board (pictured below) gives you a nice sampler. And if you can still manage it, there are plenty of good local beers and an innovative cocktail list to boot. Two other excellent nearby options are Minato, a Japanese restaurant, and Cong Tu Bot, offering Vietnamese food.

If you head over to Industrial Way area, about five miles away, there is another cluster or microbrews, including Allagash Brewing Company. Another great option is Bissell Brothers, which specializes in IPAs, and has an impressive food menu to boot.

If you do have a designated driver, Main Beer Company is less than 30 minutes drive outside of Portland, in Freeport (home to LL Bean and lots of outlets, if that might be appealing to said designated driver). They are known for their flagship “Lunch” IPA but if their impressive tasting room offers a wide range of options, some only available there. They also offer excellent pizzas and salads.

DAY 3: Back to the sea

Breakfast: If you visit Portland, you will almost inevitably be directed to try one of their potato donuts. I love potatoes in almost every form, but this seemed like a stretch. But the Holy Donut made a believer out of me. The potato makes the chew a little denser, but it’s the flavors that really elevate these (I went with the maple bacon, it being breakfast and all).

Activity 1: Taking shitty pictures of lighthouses

There is something about a lighthouse that makes people want to take a picture of it, often with themselves in front of it. Later, they will notice that this lighthouse looked a lot like that one they took a picture of a couple of years ago, lighthouses not being a form of architecture given much to innovation. And yet, the urge persists. Scratch that itch at Fort Williams Park, a 15 minute drive from downtown and the reasonably photogenic Portland Head Light.

To be fair, it looks a lot better when a professional (or even moderately competent) photographer is involved:

Another must-do in Portland is to get a lobster roll. You can do it Maine-style, which is cold and features mayonnaise. This is, per my Connecticut-raised wife, blasphemy. The only true lobster roll is Connecticut-style, which involves a simple buttered roll and buttered lobster—served hot. When we visited the lighthouse, a Bite Into Maine food truck was conveniently on hand to offer both, and the Connecticut option won favor with the skeptical Connecticut girl. No word on whether she might try the more exotic options, like wasabi or curry-flavored lobster rolls. Bite Into Maine is also available at Allgash Brewing Company. In general, the microbrews attract food trucks, an example of one of nature’s symbiotic relationships.

If you want to try a lobster roll in Portland itself, there are no shortage of options. The best may be the High Roller Lobster Co. which offers a hipster diner ambience with very well executed choices.

Activity 2: Visit Peak Island

In addition to lots of coast, Portland has a lot of islands. If you want to get out on the water, the value deal is to take one of the commuter ferries to a nearby island. We visited Peak Island for a grand total of $7.70 for our 17 minute ride. (Technically, the ticket is one way, since they don’t ask to see your ticket on the way back). Once there, you can rent a golf cart or bike, but it takes little more than an hour to get around the island on foot. If you need a break from the hustle and bustle of Portland — well, maybe city life is not for you, but Peak Island offers a low-key contrast. Befitting a small island, there are not a ton of options, but the pizza from Il Leone was great. BYOB, grab a picnic table and dine al fresco.

If you want a higher end meal, consider Street & Co which basically does very well-executed local seafood. If you did not make a reservation, this is worth a gamble since they hold 25% of tables for walk-ins. You can also visit their sister restaurant Fore Street, where the hack for last-minute dining is to turn up when they open at 5pm and settle for a bar seat with a full dinner menu. They specialize in wood fired, grilled and spit options.

With a little planning, it’s almost impossible to go wrong in a town with such a lively food scene. Check out more great restaurant options here.

Sunset on Peaks Island

This post was originally from 2022, but revised and significantly expanded in 2023. If you like this travel writing, you should probably have higher standards. Check out the archive for more about Italy, Stockholm, Copenhagen, and Salzburg.