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It’s hot in Chicago and is gonna be too hot for the next little while. It’s time to head North! Perhaps to Maine, one of the most Northern states you can get to, honestly. Once you’re in Maine, hang out in Portland, it’s one of the coolest cities in the country, full of great food, chill port city vibes, and endless, beautiful nature just a short drive from downtown. The Other Portland is a great option for a long weekend or quickie last minute vacation. Here’s what to do once you get there:


You think Maine, and a few things come to mind, right? One of them is lighthouses, and for good reason: there are a lot of them and they’re pretty goddamn neat to look at. The best/most unique one I saw on my visit is also one of the most popular: the Portland Head Light at Fort Williams Park. Situated atop a truly spectacular rocky coastline just south of downtown Portland, this is a sight to behold. Don’t have a car? Check out the truly unique Portland Observatory, situated in the historic East End neighborhood, which offers amazing views of the coast, as well as pretty much the entire city.

The Portland Head Light at Fort Williams Park

On the subject of having/not having a car, that’s something that needs to be addressed pretty early on in your plans to visit Portland. If you’re comfortable staying confined to just Downtown Portland for a short weekend trip, doing the Uber/Lyft/walking thing and taking in the many bars, restaurants, and shops, you might not need a car. Beyond that, I’d fully advise you to drive up there/get a rental, because a good amount of the coolest stuff in Portland lies just outside the city.

The Maine Wildlife Park, just a brief half hour drive up the thruway in Gray, ME, is halfway between a zoo and a state park, offering visitors an intimate look at native Maine critters like moose, eagles, bears, and more. Further down the thruway is Ogunquit Beach, one of the few sandy beaches along the notoriously rocky coast, offers a traditional beach feel while still retaining the Maine charm.

If you’ve got some spare time/the weather is cooperating, a trip to a Portland Sea Dogs game is absolutely in order. Hadlock Field, home to Portland’s Double-A Minor League Baseball team, is a charming, intimate baseball diamond with all the crowd-pleasing gimmicks, like a lighthouse that erupts with sparks anytime the Sea Dogs hit a home run, and small-time charms, like the Trash Monster, their roving secondary mascot, that come along with minor leagues.


While the Portland Airbnb scene is thriving, full of charming, affordable spots in centralized locations for the budget-conscious traveller, there are also plenty of slightly more upscale, boutique-type options, if that’s your sort of thing. First off, there’s the Press Hotel, a boutique offering from the folks at Marriott, this extremely well-reviewed spot full of vintage accents and all the contemporary amenities one would expect from a spot in their mid-tier price range (starting in the low $200s and going up from there, depending on the season).

The view from the Portland Observatory

Another high quality option is the swanky Portland Harbor Hotel, located in the Old Port neighborhood, close to downtown, as well as the waterfront. Regionally appropriate flourishes help this spot stand out from the crowd, as do the variety of vacation packages and add-ons available for more ambitious travelers. Whether you take the plunge on a fancy spot like the Portland Harbor Hotel, with rates from the high $200s, for a few nights, or a more reasonably priced Airbnb (or chain hotel spot, as there are many in the area), you can’t go wrong looking in the East and/or West Bayside neighborhoods, as well as the Old Port. They’re centrally located and a short walk from many of the best spots the city has to offer.


The last time I was in Maine, I ate lobster at least once a day for seven days straight. You should aim for a similar average, if you’re looking to maximize your Mainedom. One way to consume as much lobster as possible without breaking the bank is to focus on the lobster roll, the most Maine of sandwiches. My favorite for lobster rolls is the Bite Into Maine food cart, which is quite often conveniently located in Fort Williams Park, nearby the aforementioned Portland Headlight.

For seafood treats beyond the traditional lobster roll preparation, check out the Eventide Oyster Co., which offers elevated takes on classics like the New England Clam Chowder and lobster stew, plus a well-curated selection of oysters freshly pulled from the Maine coast and beyond. If you’ve imagined what it’d be like to chase an expertly concocted craft cocktail with a fresh-from-the-sea oyster, this is your spot.

If you’re looking for something more in the fine dining world, while still retaining the Portland feel, look no further than Fore Street. Our visit to Fore Street was an unusual one, we spent the majority of the time dodging/ogling the camera crew for the Food Network show that was there shooting for the day, showing off their open kitchen and insanely decadent offerings. It was at Fore Street that I had perhaps the best plate of food I’ve ever had in my life: their Chilled and Smoked Seafood Platter, a constantly changing selection of fish, shellfish, and other sea-dwelling critters prepared in simple, elegant ways. A spot full of brilliant dishes that let the quality of their ingredients do the talking, Fore Street is a perfect capstone on a trip to Portland.