Last weekend, I was lucky enough to go to Portland, Maine for a long weekend over Labor Day. And to be honest, I literally knew nothing about Portland, Maine – I just knew it wasn’t the one in Oregon and that I could finally fulfill my lifelong dream of eating an entire lobster. Really, it’s been on my bucket list for years (feel free to judge me, it’s the little things!)

We were headed to a wedding, so I wasn’t totally sure what to expect and how much downtime we’d have. Luckily for me, a few readers gave me some super helpful tips, and I ran into my friend Seth at the airport who just happened to be on my flight to Maine AND had spent most of his summers as a kid going to his grandmother’s house right outside of Portland. I super scored in the tips department!

So while I had a pretty whirlwind weekend, I was able to sample some of the best things the city had to offer – and I’m already planning another trip back in the near future to explore some more! Here’s what to do in Portland, Maine if you’re planning a trip there soon!

What to do in Portland, Maine Breweries:

Again, being a total Portland novice, I had no idea how many incredible breweries were in Portland before I headed there last weekend. Turns out, if you read any travel guides beforehand (unlike me, whoops!) you’ll soon find that Portland is a mecca for amazing craft breweries all around town.

Allagash Brewery:

I was lucky enough to have a tour at Allagash with a few friends, and learned so much the craft that goes into making their delicious beers, and how they are committed to being a nearly no-waste brewery. They are fiercely independent (and have time and again turned down many offers from the big guys to be bought out!) and put so much care into the beers they brew – whether they’re commercial or unique wild beers made to test out new flavors and styles. The guys there were seriously the nicest and sent us back to our AirBnB with enough beer to last us two weekends! I personally liked their more sour, funky beer they made in small batches that were available locally – but the whole tour experience was definitely one I won’t forget.

Other Breweries:

Besides Allagash, we also explored Rising Tide and Austin Street breweries, which were both equally impressive. You could probably spend a whole day touring breweries and doing a little tasting tour through the down – so if you happen to be a beer fan, make sure to visit at least a few breweries when you visit!

Where To Eat:

I was most concerned about finding the best places to eat while we were in Portland, mostly because I desperately wanted to check eating a whole lobster off my bucket list. I don’t know why, but for some reason I had this idea that it was going to be the greatest experience to have on the East Coast – and after trying a few lobsters last weekend, I’m happy I held out for the real deal 😉

If you’re not a lobster fan, there’s still tons of amazing restaurants in Portland – so much so, that Bon Appetit named the city the best restaurant city of the year this year (not to shabby!). While I didn’t have the time to do the same extensive research (I’d defer to Bon Appetit, always), here were a few of my favorite places we tried – and I few I’m regretting we didn’t make it to!

Tandem Bakery:

Tandem gets it’s own shout out because it was right by our AirBnB (score!) and we made it Saturday and Sunday because it was just that good. There was a long line outside the bakery both days, but that didn’t stop us from trying it out, and then ordering almost everything off the menu. Don’t be intimidated by the line, but definitely be prepared to wait up to 25-30 minutes to get your coffee and treats.

Everything we had was delicious, but I especially loved the blueberry scones. My friends also said nothing but amazing things about their breakfast sandwiches, cakes and epic cinnamon rolls we all ate like we’d never tasted sugar before. Next time I’m in Portland, I’ll still probably come here at least once every day I’m there – it’s just that good.

Seafood:

As it’s been super apparent throughout this silly post, I was dead determined to eat a whole lobster, so you know that as soon as I got off the airplane that I B-lined for J’s Oyster downtown. It’s a Portland original, and it’s an affordable, laid back seafood restaurant the locals love. Our waitress was kind enough to show me how to crack open a lobster, and it was beautiful to sit out by the ocean with a big glass of $5 wine (really, Chicago’s giving us a raw deal on wine pours). Get the lobster, the oysters, and the lobster roll too! Again, you might have to wait a bit, but it’s well worth it. People also let us know that Eventide was a must-go-to place (that we didn’t make it too), but friends in the wedding party raved that it was the best seafood they’ve ever had, which I definitely don’t take lightly. The brown butter lobster roll is said to be amazing, and the crudos are always a fan favorite. Our friends also mentioned that you can’t sneeze without waiting in a line in Portland during tourist season, so if you’re headed to Eventide, prepare yourself for a long wait. And if you are waiting, the Cantina across the street is known for their local brews and tequila shots!

Other places of interest include Duckfat (known for their incredible duck fat fries, and really cooking everything in duck fat), Scales for fancier seafood, and Taco Escabarr for their delicious tacos with pillowy tortillas. And if you’re still looking for some recommendations, Bon Appetit probably knows what’s up since they’re all professional eaters, unlike my novice, lobster loving self 🙂

Shopping:

While I enjoy a good shopping tour around town, my friends were far more interested in brewery hopping than trying on flannel shirts. And even though I didn’t get to do too much shopping firsthand, I heard amazing things about Portland Dry Goods (which I’d describe as hipster-chic Patagonia, if that was a thing) for all your campleisure needs. And yes, I am coining the new phrase, “campleisure” – please spread it like wildfire! (bad joke…don’t start any wildfires…)

Longfellow Books is another Portland original for new and used books that I’d love to stop into next time I’m in town after hearing of local’s love of it. Find is also supposed to be an awesome thrift store – and if you’re shopping for the whole family, Pinecone + Chickadee is adorable too!

And I would be remiss to fail to mention that a little known store called L.L. Bean is also from Maine, a little outside of Portland in Freeport. I was vetoed many times when requesting we visit the outlet, but if you have friends who also enjoy shopping from time to time, definitely make sure to visit their company store!

Cape Elizabeth:

On Sunday before I had to make my way back to Chicago, we spend the early afternoon outside of Portland in Cape Elizabeth to explore the coast and state parks, and of course eat one more lobster before I left. We walked around Two Lights State Park and spent most of the afternoon tackling the rocky coastline where the rocks looked more like ancient logs than actual rocks. It was a beautiful place to watch the waves roll in, and between the rocks there were tons of tide pools with crabs, mussels and other little sea creatures. We probably walked a mile or so around the coastline and then turned back around to eat at the Lobster Shack, another local favorite in the area. It was another long wait (so be prepared!) but the lobster was delicious, and I ate a whole side of fries a little too quickly. It’s quite the experience and well worth the wait!

Since I was only there for a few days, we tried to squeeze in as much as possible – but again, I’m definitely looking forward to going back to visit Portland again soon! I’ve already started seeding the idea to my parents too to see if they’ll get in on the party too 😉

Hopefully this helped you figure out what to do in Portland, Maine in case you’re planning a trip too! And since I’m planning my next trip – please share what your favorite things are to do too! I’ll make sure to update this post as I have more favorite places to add in. xx