Weekend Guide to Portland, Maine

I love New England. There's something about it that feels strangely like home to me, even though I'm not from the area at all. While I've visited several cities in the region for weekend trips, I had yet to check off that weekend trip to Portland, Maine I had been wanting to take for so long. 

When the opportunity came up, I immediately jumped on it to make it work. It's a decent drive (about 5.5 hours with no stops) from NYC to Maine, so I wanted to maximize my time in Portland to fit as much as possible into a single weekend.  

I knew to expect beautiful coastal scenery, lighthouses, a lot of lobster (So. Much. Lobster.), and a cute town, but what I didn't realize was how detail-oriented everything was and how friendly everyone is. The attentiveness to local everything in Portland, even in the little details, is what stood out most. Not only is it the norm to source from local farms around Maine and Vermont, but there aren't a ton of mainstream franchises here. It's all local, family-owned businesses with their unique takes on local foods and goods. Needless to say, I loved every bit of it!

Before embarking on the roadtrip up to Maine, I (along with help from my girl Mary Catherine) sourced together a list of places we wanted to go explore, but we also discovered even more while we were there.

So, I'm sharing this comprehensive guide with you guys for the ultimate weekend guide to Portland, Maine! Everything you've come to expect from my city guides and #TravelingMinnaly, from where to stay, where to eat/drink, and where to explore. There's a roundup at the bottom of the post, for those who want to skip through the photos (but you shouldn't). 

I'm also going to share some places we didn't make it to but that came highly recommended to us, along with some places I don't have photos of because it was so dark at night. 


Black Point Inn

I wrote about my wonderful experience at this beautifully historic luxury inn HERE.
It's a scenic 20 minute drive from the heart of Portland, and it is the perfect reclusive New England getaway for all occasions. Ocean views, lush greenery, warm hospitality, and plenty of amenities, Black Point Inn wins my vote.


For Coffee + Pastries:


Super adorable coffeeshop with an abundance of unique pastries ("everything" scone, banana black sesame loaf, those cinnamon rolls, but I would have gone for the biscuit with jam if I could eat gluten!) and some delicious coffee. Would be hard to have a bad start to the morning here!


This place had some delicious pourovers, and is clearly a go-to spot for people looking to work on their laptops. Was much quieter than Tandem, if you're looking for a spot to wind down a bit.


This place is famous for their potato donuts AND I was beyond ecstatic to find out they had multiple gluten-free donut options too! I loved the lemon glaze, while apparently the original potato donut lived up to its awesome reputation


For That Lobster Roll, Seafood, and Good Eats


Located right on the harbor with some beautiful views, Scales is an all-around winner. The lobster roll was a hit, the lobster bisque was so satisfying without being heavy, the steamed mussels in buttermilk were divine, and they have gluten-free cornbread! A great place to go to fit all palates and dietary preferences.


You can read all about my magical experience here, but truly a can't miss. Such creative cocktails that taste amazing, inventive southeast Asian fare, a lobster tasting menu, what more could you ask for when looking for a treat-yoself dinner?

Other Recommendations:

Eventide Oyster Co- Sad to say we missed this one, since we were still so full from our dinner at Tempo Dulu, BUT I got this recommendation from 5 people and the place looks amazing. The dashi chowder also sounds unreal.
The Honey Paw- Homemade noodles, lobster wontons, fry bread + uni butter. Nuff said. 
Central Provisions- A trendy spot by the harbor, the crudo is apparently not to be missed.
East Ender- A gastropub with everything from Korean to Latin American.
Dutch's Portland- All about the breakfast sandwiches here.


For Cocktails and Non-Alcoholic Drinks


It's gotta be mentioned twice, because the cocktail experience and bar is an entirely amazing experience on it's own. Get the award-winning Jakarta, or the Wayang (pictured above).


So sad I don't have photos since it was so dark inside, but such an awesome spot. They have fizzes, shrubs, mocktails, and cocktails, all using an impressive array of house-made bitters. They also have an expansive little shop for anyone interested in craft cocktails- everything from shakers, bitters, books, it's an amazing spot for an aspiring cocktail master!


Ciders, Meads, Kombuchas, galore! All made from local apples and made in house. Can we bring this to NYC? $5 for a tasting flight of any 5 drinks you choose. The strawberry mead was my favorite- but be careful, it's strong!

Other Recommendations:

Drifter's Wife- We missed this because of timing, but this gorgeous wine bar is still on my list!
Liquid Riot- A brewery/distillery/resto-bar, it's a one-stop shop for everyone.

Where to Shop


Do not miss this store. I repeat, do not miss this store. Kitchenware, antiques, bath, baby stuff, home decor, candles, it's seriously my dream store. It's like Anthropologie but specially curated from unique sellers in France, Japan, and right here in the US. I got a lovie for my pregnant sister, some candles for mom, and had to stop myself from taking all the serving ware home!


For the chef or the perfect gift shop for any foodie, this salt store is amazing! Everything from Himalayan pink salt blocks, to espresso salt, this was such a cool find to stumble upon. 

Where to Explore

The Harbor

Nothing much to say here, but the harbor is so fun to walk around and see all the pretty boats. Cobblestone streets, souvenir stores, mom + pop stores, all too cute to miss.

Portland Head Light

There's not much to say about this one other than the obvious.

Maine is known for it's iconic lighthouses that decorate the coast of New England. The Portland Head Light is probably one of the most-often photographed one of the bunch in this area. Located in Cape Elizabeth, it is about a 15 minute drive from the heart of Portland city center. You'll drive up to Fort Williams Park, where there are some picnic benches and areas to explore. Go a bit further in and you will reach the picturesque view that is asking to be Instagrammed.

L.L. Bean Flagship

A 15 minute drive out of Portland will take you to Freeport, the home of the famous L.L. Bean Headquarters and campus. It is quite literally a campus, with separate buildings for hunting/fishing, apparel, home, etc. It is definitely worth a visit to go explore, and don't forget to take a picture in front of the famous boot!

Other Recommendations:

Portland Museum of Art- Heard great things about this museum; great for a rainy day!
Portland Freedom Trail- Basically downtown Portland, but this map notes historical landmarks
Peaks Island Ferry- Ferry around Casco Bay, for when the weather is nice

Other than that, simply walk around downtown and wander the streets, the harbor, and lots of fun little shops to duck into to explore. You will find a TON of lobster memorabilia!

Special thanks to The Black Point Inn and Tempo Dulu for hosting and welcoming Living Minnaly. As always, all opinions and reviews are my own.