Portland, Maine: Ideas for a Fun New England Trip!

“What’s an easy trip from Boston for a romantic getaway?”

I pondered this aloud, zooming out the map. “Where can we get a great New England vacation with less than 2 hours of driving?”

Ah! Portland, Maine popped into view. Memories flowed of friends gushing: “Portland is delicious. Go there and EAT.”

Food tourism? Decision made.

My husband and I packed the car, waved a passionate thank you to our parents for babysitting the kids, and sped north for our first couples’ trip since our son was born 4 years ago.

What follows is a chronicle of our 2.5-day getaway to give YOU ideas on…

…What to do — and eat — in Portland, Maine!

The Best Activity We Did in Portland:

Ok, so this is kind of awkward, but we pretty much just ate for three days straight. Our activities were picked simply to pass the time between eating again. That said, there was one between-meals activity that stood out as our favorite: The Escape Room.

(Before I show the picture and explain what it is, a disclaimer: My husband likes to make ridiculous faces in all our photos. You have been warned.)

In The Escape Room, you have one hour to solve a series of puzzles in one of three themed rooms in order to unlock the exit. We chose “Copperhead Saloon” and were locked in with a random family of four to face the challenge.

Two things blew my mind about this activity. First, was the brilliance of the puzzles. As an English teacher, I see hidden meanings all over the universe, but most don’t actually exist. In The Escape Room, however, everything has a true hidden meaning. I can’t say anything more without giving away the secrets, but let’s just say that if you see something a tiny bit odd anywhere in the room, there’s a reason for it, and a hint hidden therein.

Second, every person in your team has something to offer. When we were placed with the random family — including their two young kids — I snobbishly thought, “That young boy will just slow us down.” However, I was a fool, because the lad ended up solving two of the hardest puzzles, and his size proved an asset in seeing a next step.

Are there other activities in Portland? Of course! There’s live music, massages, theatre, and even a Cryptozoology Museum (to explore Bigfoot?!), and much more. But the highlight of Portland is… the food.

Food in Portland, ME: Where to Eat!

The best meal we ate in Portland, Maine knocked our socks off so far that those socks are likely now all the way in Portland, Oregon. That stupendous meal was dinner at Bolster, Snow, and Co. nestled in the first floor of a hotel called (affiliate link) The Francis.

The key was the freshness, and the artful combinations of flavors. I ate the best salad of my life that night, among six other stellar dishes. How good was the food? I had a 10% off coupon from Yelp, and decided NOT to use it because I literally wanted to pay every penny to honor that food.

Painful December 2018 update: Alas, Bolster, Snow, & Co. has announced they are closing! I will follow the chef to find out where he ends up. Sniffle!

Right across from Bolster, Snow, and Co. is a coffee shop you must check out: Tandem. This cafe is located inside an old-fashioned gas station! That detail highlights the zingy ways in which Portland merges old, new, food, and art.

Tandem was actually the first place we went in Portland, and its bright walls and exciting pastries set the artsy-foodie tone perfectly for the whole trip. I mean, where else can you get a goat-cheese, honey, fennel scone?? (I think Portland has a crush on fennel as a flavor.)

It was a darn good scone. Can you almost taste the crispy exterior and butter-fluffed interior through the screen?

By the way, there’s a meal missing from these photos… it’s the epic tasting menu at EVO that I spent my whole first Portland, ME article explaining! Just click on over to that link if you want to see it.

Meanwhile, back at Tandem… even the spiraled table legs were cool.

Next up for deliciousness was Central Provisions. This restaurant earned rave recommendations from all our Portland-loving friends, and indeed was scrumptious — and gorgeous.

Our favorite dish was the tuna crudo, and speaking of raw, we also tried the famed raw beef salad, which made me feel like a powerful caveman. Sorry — my photos of it just look obscene, so you’ll have to visualize what a raw beef salad looks like and be content with a pretty BEET salad instead. (Oh, how much changes with a single letter.)

The surprise dish of Central Provisions — which we’re thankful to a friend for recommending — was the “Bread and Butter” pictured below. I thought it would be hum-drum standard bread and butter, but turns out there’s caviar in it! Among other hidden magic.

At the next spot, we made a tactical error. The restaurant was the famed casual eatery, Dutch’s. The biscuit sandwich pictured below was SO GOOD, as were the hash browns.

So what was the tactical mistake we made there? We didn’t honor that those hash browns are SERIOUS business. If your aim in Portland, as ours was, is to eat all day, do not eat 100% of Dutch’s potatoes on your plate, delicious as they are. For if you do, you will not be hungry again for hours, despite yearning to consume more food. Powerful potatoes!

Tip: Peek at the bathroom decor at Dutch’s! It’s a hoot, but I didn’t want to photograph it because it just felt creepy bringing my giant camera into the bathroom.

Get a flavor for the decorations at Dutch’s from this wall view, below. Oh, and if you’re enjoying my fashion in this article, find out more about the travel dresses here!

Bellies still rotund from Dutch’s 3 hours later, Colin and I decided on a “light soup lunch” at Pai Men Miyake.

The “light” part of the equation was slapped in the face when we opted for the $2 Brussels sprouts side dish add-on to our ramen (“How big can a $2 side dish be?”)… and ended up with our table packed to its edges with all the food pictured below. Needless to say, after that meal, our bellies could fit no more before sleep.

The following day, refreshed in belly and soul, my spouse and I moseyed to the laid-back Ohno Cafe for bagel sandwiches, that were just the thing. The local Coffee by Design (CBD) served there was the best coffee I’ve had in a while — and I drink a lot of coffee to keep up with juggling the parts of my life right now!

Now, we couldn’t leave Portland without dessert for the road, right? After an agonizing debate about which gelato spot was best, we opted for Gelato Fiasco. Turns out that even in a size Small, you still can put in as many flavors as you want! Ever the indecisive Libra, I squeezed (squoze?) 4 tastes into my cup.

Sigh… We didn’t even scratch the surface of the world-class food that exists in Portland (Duckfat fries, I’m looking at you), but at least we got started and gave it a taste. Now, if you know the city, I’m curious for you to leave your restaurant recommendations in the comments!

The Portland Museum of Art:

Full as heck and need a stroll and some culture? The relaxed and welcoming Portland Museum of Art is the place to go. Here are some of my favorite works of art in the building… not including the Picasso that I was politely instructed was off-limits to photograph.

Excellent Views of Portland from Above:

Is your art stomach satiated? For the next activity, ’tis always a thrill to ogle the city one is visiting from a high-up vantage point. Head to the (affiliate link) Westin Hotel‘s highest floor, Top of the East, which is open to the public as a restaurant, and provides exceptional panoramic sights of Portland. The lounge has been open since 1963, and is a perfect afternoon beverage-and-views break.

For an outdoor option, North Street Park is on a hill that overlooks downtown.

The Portland Head Light: A Must-See Lighthouse!

Now, no matter how short your visit to Portland, you MUST visit the Portland Head Light. This lighthouse stands on Cape Elizabeth, a mere 15 minute drive from Portland. If you’re looking for a romantic place to stay, Inn by the Sea, Maine is right nearby.

It was built in 1791 (that’s historic!) and by some measurements, is the most photographed lighthouse in the country. Just be sure to pack layers, because it sure gets blustery with all those ocean breezes!

Where to Stay in Portland, Maine:

Convinced a trip to Portland is for you? Now comes the bed-planning part! (Note: Accommodation links here are affiliates that provide a small commission at no extra cost to you. Note #2: Don’t mix up Portland, ME with Portsmouth, NH and book a hotel for the wrong city!)

During our Portland stay, we were guests at the Holiday Inn by the Bay and enjoyed a comfortable room on the 10th floor with panoramic views of Portland’s harbor. A major perk of that hotel is its perfectly located between the Arts District and the delicious central Old Port area. We parked our car in the garage and didn’t need to take it out once except for the lighthouse trip.

That Holiday Inn is also host to a number of gatherings and conferences because of its ample space… including the 2019 Women in Travel Summit (WITS) run by my friend Beth!

If you’re seeking a character-filled boutique hotel experience, the Press Hotel is where to stay, as the entire building is decorated with newspaper-themed items… including typewriters hanging off its walls.

Finally, Portland has some great options for renting houses and condos through Vrbo — economical options if you’re traveling with kids or a larger group.

See Why Portland is the Perfect New England Mini-Vacation?

We loved our Portland getaway, and think you will too! If you haven’t been, what are you most intrigued by? If you have visited already, what advice would you add? Do share!

Looking for other New England Getaways? Try Woodstock, VT or Provincetown, MA!

We were guests of Visit Portland and the Holiday Inn by the Bay, but all opinions and gluttony are my own.