I popped up to the pine tree state for a few days to attend the Women in Travel Summit, and I was absolutely charmed! Here are all the unique things to do in Portland, Maine if you find yourself visiting. Just a warning, they’re probably 90% food-related.

Surprise! I went up to Maine recently when I said I was hunkering down for the month to get ahead on work. The lovely Alex from Alex in Wanderland asked me if I wanted to go since she had an extra ticket. I looked up some accommodation options and the logistics of driving up, and thought, “Why not?!” 

It was such a great weekend! I always get anxious thinking about attending conferences, and then I wind up have the best time. It’s not everyday you get to hangout with people who love travel like you do, and, wow, did WITS bring some incredibly inspiring speakers this year! Seriously, just look up Deesha Dyer and Deidre Mathis.

Of course, in between the conference talks and sessions, I wanted to get to know Portland! Between saving some places on my phone, chatting with my hostel roomies, and asking random locals about the city, I wound up doing quite a lot in only a few days. Here’s all I got up to!

Why Visit Portland, Maine

If you’re not familiar with Maine or New England, there’s a certain vibe to the area that’s quite unique. See Taylor Swift’s Red era when she was dating the Kennedy kid or, you know, the Kennedy family and Hyannis Port, but maybe not as WASP-y.

Portland, which is more in southern Maine, embodies all of it and mixes it with what feels like a bit of its own hipster touch. Oh, and, of course, layers it all with an abundance of delicious food and restaurants with their own personality. 

Map of Things to Do in Portland Maine

Tips for Visiting Portland 

Where to Stay

Budget: Black Elephant Hostel

This is where I stayed! It’s hands down one of the cutest hostels I think I’ve ever stayed at. I mean, just look at that pupper modeling like it’s his day job. (Sadly it seems he’s since passed!)

The hostel isn’t right in the center, but it’s kind of a nice midpoint between the waterfront and Portland Observatory and downtown. I slept in a 6-bed female dorm, and my roommates were awesome! We chatted about where to eat, the conference, and just travel in general. It was a pretty spacious room, and we had our own bathroom plus bathrooms in the hall and a nice sink area.

Book on Booking or Hotels.com

Mid-Range: Holiday Inn by the Bay

This is where we had our conference, so I thought I’d add it as a bit of a mid-range option (still around $200+ a night). It’s very close to everything downtown and across the street from the Portland Museum of Art. 

Book on Booking or Hotels.com

Luxury: Press Hotel

I feel like if you want a luxury stay and you find an Autograph Collection hotel, stay there! All the hotels are independently owned and operated, so they remain unique, and often the designs fit the vibe of the city they’re in. I stayed at one in Kissimmee, and I’m still so obsessed with the decor there.

The Press Hotel is right in the middle of downtown, and I walked by it frequently visiting other places. Of course, peeking at photos, it’s easy to see how beautifully it’s decorated!

Book on Booking or Hotels.com


I just switched to AT&T on my recent trip home since T-Mobile was crap abroad and I never seemed to get even semi-decent service stateside. I had plenty of service in Portland and never had an issue connecting to data. 

Wifi was also fine most places I went. It was a little wonky at the Holiday Inn, but I also assume that has to do with the fact that a giant conference of female travelers was going on, and we all are digitally connected.

You should be able to pick up a SIM card at the airports, but if you can’t, try to get to an AT&T store, and they can help get you set up. 

What to Pack/Expect for Weather

I can’t believe I forgot this, but Maine is kind of cold! Now that I’ve been back, I remember camping in Bar Harbor and wearing the same long jeans everyday because it was so cold in the summer. Portland in early May is no exception. I was dressed poorly for the entire trip with summery dresses, skirts, and sandals. 

If I was repacking, I’d bring my trench coat and pack some nice slacks and pants with some cute tops instead of dresses. I’d also swap out my sandals for my loafers.

Transportation Logistics

Getting in

The closest airport to Portland is Portland International Jetport (PWM) and it’s only a 10-minute drive to downtown Portland. You can easily grab a Lyft over or rent a car. 

How to Get Around

Portland is pretty walkable if you’re worried about renting a car. And if you walk too far and don’t want to walk back, there are plenty of Lyfts. Bug Lighthouse and Portland Lighthouse are a bit of a drive away, so you’ll probably want to drive to them.

I personally drove since I had my car and I needed to keep moving it. The parking near Black Elephant was only 2 hours between 9am – 5pm but free the rest of the day, so I constantly drove it over to the Holiday Inn, where we had free parking for the conference.

26 Unique Things to Do in Portland Maine

1. Grab a donut at Holy Donut

My friend RAVED about these donuts when I told her I was going to Portland. She said they’re even better than the Duck donuts I dream about from Ocean City, MD. 

Naturally, I went to try one. There are three locations: Park Ave., Exchange Street, and Scarborough, and I went to the Exchange Street one and, later, to the Scarborough one. They’re made from as many local ingredients as possible, and the Maine one is — potatoes! (Get it main, Maine, heh heh). 

They’re freaking delicious, and I didn’t even know about how much healthier and more locally-sourced they are when I got them! My first taste was toasted coconut, and then I picked up a half dozen to bring back to Corinne. I can’t remember which ones I got, but my favorite was maple bacon! 

2. Get a lobster roll at Portland Lobster Co

As soon as I rolled into Portland, I stopped here for a late lunch! It was my first experience of the city, and it was such a nice one at that. The cashier was so lovely, and the lobster roll was amazing. They also serve local Maine Root soda, which made me then ask for it everywhere I went. All their seafood is locally-sourced and as organic as they can make it. Even their straws are biodegradable in case you forget your own.

Highly recommend sitting outside. If it’s cold out, they have a heated tent section.

3. Check out the books at Longfellow Books

Okay, there are quite a few bookstores I saw around Portland, but I saw Longfellow recommended the most, and I loved it. I got two used books, a cute notebook, and the most adorable card with “There She Goes” on it! Can you tell I’m a sucker for bookstores? 

4. Grab a cone at Mount Desert Ice Cream

Before a WITS happy hour, I met up with Alex at Mount Desert Ice Cream (which, lol to ice cream when we’re freezing in the drizzly weather). All their ice cream is totally homemade. I loved the Maine sea salt caramel flavor.

5. Try the Chinese at Empire Chinese Kitchen.

So when I was checking out at Longfellows, I asked the woman at the register if she had any favorite places to eat in Portland. Empire was one of those places, and we wound up there after the conference finished the first day. 

DELICIOUS. There’s usually a bit of a wait for dinner, so I’d reserve ahead if you can. They even have soup dumplings, and the soup-meat ratio was on point. On par with the ones I had at Din Tai Fung in Kuala Lumpur. I also got duck ramen which was also mouth-watering.

6. Get a giant slice of pizza at Slab

Another place she mentioned was Slab pizza! Holy pizza, guys. It’s HUGE. Don’t get more than one slice because you probably won’t even be able to finish it. Also get the root beer with it, yum!

7. Dine at DiMillo’s on the Water

We had happy hour at DiMillo’s and it was a fun place to mingle and chat. The restaurant is on a ship in the marina, and you can grab dinner or lunch there.

8. Grab some fish and chips at Tomaso’s Canteen

We went here after finding out Eventide had an hour wait. It’s a casual bar right near Black Elephant Hostel, and the fish and chips were especially good! 

9. Walk around Old Port.

Of course, the best way to get to know the town is to walk around the Old Port. I did a little walking on my first day. It’s a super walkable city, especially the downtown area since everything is pretty much with in a 1/2 mile radius.

Old Port Tours

10. Sip on some tea and get cozy at Dobra’s Tea Room

I mean, Maine was drizzly and cold in early May, so I can’t imagine how it is in the fall, winter, and early spring! Cue a nice hang out session at Dobra’s Tea Room, probably the coziest places I visited on my trip.

They even have those nice dais beds where you need to take off you shoes to sit and enjoy. Choose from a ton of teas from around the world. I loved the one I got. I can’t remember the name, but it was third on the menu of flowering teas, and I had it with matcha cheesecake.

11. Eat lunch at Green Elephant

I say lunch because Corinne told me she tried eating there for dinner, and it had a crazy waitlist, so you may have better luck at lunch. This was the third place the Longfellow cashier told me about, and I’d say she was 3/3 on her recommendations!

The Green Elephant will be awesome if you’re with vegans or vegetarians. It started in 2007 to be the ultimate place for vegetarians in Portland, and many of its dishes are Asian-inspired. Definitely get the Pad Thai and then sorbet for dessert! I did try the Mexicane cola here and didn’t love it as much as the root beer from Slab.

12. Get some Italian at Paciarino

Rae and I got dinner here! She said she was craving pasta, so I looked up nearby Italian places and Paciarino was the closest one! They hand make their pasta and sauces everyday, and the ravioli milano was so, so good. Our waiter also recommended our next stop!

13. Eat gelato at the CUTEST gelato place in the USA

If you get gelato anywhere in Portland, get it at Gorgeous Gelato, which is maybe a 5-minute walk from Paciarino. Don’t let the line phase you, there won’t be much of a wait, and the owners were so sweet. We spoke with Mariagrazia as we were paying, and she wound up recommending a gelato shop for me to try in Milan (will update with that one). 

The gelato and canoli we got were, of course, delicious!

14. Go to an event at the Grace

We had our opening party here! It was once a historic church and was redesigned as an event space. While it’s probably more used for things like conferences and weddings, they do have other events, like yoga! Just check their site for anything you might want to go to. 

15. See Portland Observatory

The Portland Observatory was originally built in 1807 and is now the only one of its kind still left. It’s 86ft (26m) high. Basically, because of the way the harbor is, not all ships were easily visible as they were coming in. So, they built this observatory so that people in the wharfs and the ocean could see it. 

I wasn’t in Portland in season, so it was closed, but if you go between late May and mid-October, you can take a guided tour. It’s $10 for adults and will, of course, give you a pretty view of the city!

16. French pastries at BLVL

Stop by BLVL or Belleville after you check out the Portland Observatory for some delicious French pastries. I actually parked next to it without realizing it was a cafe, so I was happy to not have to stop off elsewhere for coffee. Their ice coffee was a bit too strong for me, but I’m also still getting over not putting heaps of creamer and sugar in mine, so if you’re a regular coffee drinker, you might love it. The pastry I got with an egg in the middle, though, was delicious.

17. Check out the Portland Lighthouse

Take the morning and drive out to the Portland Head Lighthouse in Cape Elizabeth! If you want to spend the day outside, you can enjoy the whole Fort Williams Park. The lighthouse was first built in 1791 and is 101ft (31m) high. It’s considered the oldest in the whole state.

The drive is pretty easy and only takes maybe 15-minutes. If you go during the weekend, you can visit the Lighthouse Museum for $2. 

Tours to Portland’s Lighthouses

18. Then pop over to Bug Light and see some harbor views of Portland

On your way back into Portland head to Bug Light Park! Bug Light, which is officially known as the Portland Breakwater Lighthouse, is a cute, tiny lil thing. It was first constructed in 1855 and the current tower is from 1875. It’s tiny compared to just about any other lighthouse I’ve seen at only 30ft (9.1m)! 

And, of course, the park is a great place to see views of the harbor and Portland from afar! Can you see the Portland Observatory peeking out?

19. Enjoy the Eastern Promenade/waterfront

If the weather is nice, go for a walk around the waterfront! It’s just a nice, quiet area with pretty views.

Unique Things to Do in Portland, Maine that I Didn’t Do Yet

20. Check out Portland’s many breweries – I don’t drink beer, so I, of course, am not the target market for this one! However, Portland has a ton of cool breweries. You can check them out on your own, or try a craft drink tour, like this one. There’s also this bikes and brews tour if you want to mix in some sightseeing or this brews cruise if you want to kick back on the water.

21. Go to Duckfat – I want to try those fries fried in duck fat!

22. Eat at Eventide Oyster Co. – Everyone raved about this place, but the only time we were planning on going, it was an hour wait and you can’t call ahead. Next time!

23. Portland Art Walk & Portland Museum of Art – On the first Friday of every month, you can go on an art walk around the town and the PMoA is free! It was too cold and rainy the Friday I was there, so I didn’t want to stay outside too long.

24. Victoria Mansion – Want to see how the wealthy New Englanders lived in the 19th century? Take a tour of Victoria Mansion! WITS had some tours, but you needed to pre-register and I was too late.

25. Two Lights State Park – Another lighthouse! I wish I had seen it on the map beforehand, and I would have made to stop by.

26. Island Hopping – There are so many islands near Portland! I want to try to see more of them if I go back, but I haven’t done much more research beyond jotting down some names. 

For more on Portland:

And there you have it! A fun, little guide on all the unique things to do in Portland, Maine!

for more travel in the usa

The USA is a massive country, and I always love discovering new places to visit. I’m actually pretty sure I’ll still be hearing of new gems when I’m 90 years old and need a wheelchair to get around! Since I’ve been interested in travel, I’ve visited a number of different places in the US alone. Check out some of posts:

Popular Posts

New York Travel

California Travel

Florida Travel

New Orleans Trip

share this on pinterest

want to support?

I’m always grateful when friends and readereach out wanting to support There She Goes Again. Truthfully, I’m just happy my posts are helping people travel! If you’d like to support the blog, here are some companies and brands I’m affiliated with. Simply click the links, and I receive a small commission at no extra cost to you!


  1. Hi Samantha,
    You mentioned “Portland Lighthouse” but the correct name is “Portland Headlight” or Portland Head, as some of us natives call it. By the way, poet Henry Wadsworth Longfellow would walk from his Portland home to Portland Head frequently. He was internationally known in his day.

    I’m so glad that you mentioned Victoria Mansion, which is the work of a nationally distinguished architect and this is his only surviving work.

    For historic cemetery fans, there’s Eastern Cemetery and their Spirits Alive tours are wonderful. And Friends of Evergreen Cemetery offer docent-led tours, which often are theme-based. “Suffragettes” “Sea Captains” “Civil War”
    I’m glad that you enjoyed visiting my hometown. I cherish that place and its culture.
    Best wishes and happy travels, Patricia

  2. Being a sucker for bookstores like you makes me want to visit Maine ASAP. I can’t wait to get my hands on those cute little notebooks. The pictures of donuts & ice cream make me drool. Hanging out at Dobra’s is definitely on my bucket list…

  3. Samantha,
    I have lived in Portland for over 30 years. You did a great job of covering all of our favorite places. I totally agree when you come back you definitely have to have the worlds best French fries at DuckFat. Oh and some people will be excited to hear that because of Covid and many many restaurants moving their dining outside, yes in tents in the winter, Portland has decided to close many of the streets in the Old Port so it will be foot traffic only. 47 restaurants have agreed to go along with inside and outside dining. Similar to Burlington VT. So you and all your readers definitely come back! It’s so exciting your plan to visit the world. You go girl!!!

    1. Hi Susan, thank you for your kind words! Ugh just saying “french fries at DuckFat” has me salivating, I can’t wait to finally try them. That’s so cool about some streets being foot traffic only and how many restaurants agreed to outside dining. And aw thank you! I do love travel ha!

  4. I was just looking at blog names and thought yours was perfect; and low and behold the post that came up was this one, where I am from! Great post! Recommendations if you come up again Thai food from Boda, stand up paddle board yoga by Portland Paddle, coffee from a Coffee by Design and an event at Thompson’s Point!

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.