24 Hours in Portland, Maine

Maybe this city doesn’t have a sketch comedy show named after it, but it still has all the gentrified hipster charm you’d expect from a city with its name. Whether you’re escaping Boston for a weekend or driving through on your way to Acadia, Portland is a small, charming city that’s great for a short visit. Here’s how I spent my 24 hours in Portland:

Friday night: Dinner and a Stroll

I suggest filling up at Black Cow, an upscale burger joint where you can pretend to be healthy by ordering a side of 2021’s trendiest vegetable, brussels sprouts. Eat on the patio, then window shop and wander through downtown Portland. If you are looking for an activity a bit more particular to the city, try seeing how many of these inexplicably ubiquitous Rick Moranis stickers you can find.

Raspberry jam is actually illegal here.

Saturday Morning: A Picnic Breakfast at Fort Williams State Park

Real estate investors, your time is now. South Portland is on the ups, and you still have time to get in before every block has an artisinal CBD-infused soap store. Scout properties as you head to Cia Cafe to pick up breakfast and coffee, and then make a quick drive to Fort Williams State Park, where you can spend the morning exploring old forts and strolling the park’s easy walking paths. It’s a low-effort, high-reward kind of outdoor excursion, meaning with little leg work, you can get views like this:

And this:

Of course, if you’re feeling adventurous and want to scramble on the rocks, go ahead! After all, we’ll be eating lunch pretty soon, and you’ll want to have room for…


The Borscht Belt has expanded, folks. It is now possible to purchase sweet and savory knishes in the great state of Maine at BenReuben’s Knishery, where you can also find excellent kugel and rugelach gems.

But also, a disclaimer: I am a mere appropriator of Jewish culture. Everything I know about Ashkenazi cuisine, I know because of boyfriend. When I was reading names of restaurants out loud to him, I asked him, “What’s a k-nish?” and weeks later, he is still laughing about it.

Saturday Afternoon: The Portland Museum of Art

They have Renoirs, so you know they’re legit.

Get cultured, idiots! Admire the fine works of Winslow Homer, Edward Hopper, and other world-class artists right in the middle of downtown Portland. If you’re put off by the admission fee, plan to go on Friday instead — that’s when entrance is free.

When you’re done, reward yourself with a scoop from Mount Desert Ice Cream. As you’re walking back to your car, jot down all the names of restaurants you want to visit next time. I promise you’ll be back.