Day: October 22, 2024

Date Published: Oct 22nd, 2024 | Last Updated: April 22nd, 2025
Author: Abby | Category: Travel, USA
Date of travel: Aug 5th, 2025

Portland is the largest city in Maine, full of cool shops and endless lobster rolls. Spend an afternoon here walking through the old streets, sample the abundant seafood, and take a tour around town.

Fun fact: Although Portland is the largest city in Maine, the capitol is actually Augusta!

We originally did this trip in August 2024 on our way up from New York to Rockland for the lobster festival (you can read about the lobster festival here). We stopped by Portland on our way home and spent the afternoon here walking through the streets and perusing through the variety shops ranging from cool hipster vibes to fancy boutiques. There’s a LOT of restaurants here, not just seafood. Sadly, due to our short time here and limited stomach capacity, we were only able to hit up a few places, but the next time we come back I’ll definitely be crossing more off my list!

Below is a map of downtown Portland divided into 4 regions: the arts district, government district, old port district, and waterfront district. The majority of the shops and restaurants are in the old port district (in red).

What to do in Portland: Shop, Eat, and Explore!

We only had an afternoon here and from my research on Portland, we’ve hit up the most popular places. We do plan to come back again in the near future and explore some more, so I’ll be updating this post when we do – keep watching this space!

1) Shop

Commercial Street

Walk along Commercial Street and you’ll find many cute boutique and souvenir/gift shops lined up one after another. This street is right by the harbour and is one of the busiest touristy streets for shopping. It’s highlighted in the map above.

Exchange Street

Exchange Street is another street full of shops. This street is more tucked away compared to Commercial Street but I found the shops here to be a lot more interesting with a cool hipster vibe. There’s restaurants along this street as well with some nice coffee shops. I found this street to have more character compared to the more tourist-y Commercial Street. This street is also highlighted in the map above.

2) Eat

When in Maine…eat Lobster Rolls! There is no doubt an abundance of seafood in Maine and we had nothing but seafood on our brains so that’s what we focused on, but there were tons of other non-seafood restaurants that looked amazing as we walked by. In my research, the consensus for the top 3 places for lobster rolls were: Luke’s Lobster, Highroller, and Portland Lobster Company.

Portland Lobster Co.

Address: 180 Commercial St, Portland, ME 04101

Portland Seafood Co is a small shop on the harbour with limited seating inside the restaurant, but there’s a huge open back patio by the water where you can easily grab a seat. We went right when they opened and there were already a few people there. They have a decent sized menu and the prices were fair. They’re well known for their lobster rolls, but Toby really wanted to try the Lobster BLT since we had never seen it before – it was REALLY good and they were generous with the lobster meat. I had a classic steamed lobster. Unfortunately I had a bad time with gastro from an earlier donut shop (more on that later) so I couldn’t fully enjoy the extent of the meal, but from the bites I had, it was delicious. Toby was more than happy to help me finish my lobster.

Luke’s Lobster

Address: 60 Portland Pier, Portland, ME 04101

Everyone was going to Luke’s or talking about Luke’s. It’s probably the most popular lobster roll spot in Portland and it’s also situated right on the water. We didn’t end up coming here because we’ve had Luke’s in NYC (it is indeed damn good) and wanted to try something new. If you’ve never had Luke’s before, I’d highly recommend coming here.

Highroller Lobster Co.

Address: 104 Exchange St, Portland, ME 04101

Highroller Lobster Co. had really cool vibes and it was super busy. We needed to get on the road and we were still full from Portland Lobster Co. so we decided to grab takeout instead of sitting down in the restaurant. The takeout menu was much smaller, but we were mainly here to try out their lobster roll anyway so we didn’t mind (although there were some amazing looking dishes on the full menu – I’ve included photos of both the dine-in and the takeaway menu). We ordered two 2oz lobster rolls that was $17 each. Super pricy and it was also SUPER TINY 💔. The bread was good and it was a decent lobster roll, but for the long time we had to wait and the small portion, it wasn’t THAT good. Next time maybe we’ll go for dine-in and get more variety.

Duckfat

Address: 43 Middle St, Portland, ME 04101

Not seafood, but I thought I’d include it due to the sheer popularity of this place and how every single travel blog mentions it. This place was even featured on an episode of ‘Somebody Feed Phil’. Duckfat is known for their Belgian-style french fries that are cooked in, you guessed it, duck fat! Their poutine is the go-to most popular item. Unfortunately we did not get to try this place because when we arrived, the line was super long and it would’ve been at least an hour wait. We were still full from all the lobster rolls anyway and we also still had a 7 hour drive ahead of us, so we didn’t wait. They don’t take reservations, it’s walk-in only, but you can pre-order and have it as takeaway – something we didn’t realize until we got there.

They do have a second location that only does takeaway called Duckfat Frites Shack (43 Washington Ave, Portland, ME 04101) that may have faster service. It’s another 10 min walk that we didn’t take because by then we would’ve been too far from our car. Womp womp.

The Holy Donut 🙅🏻‍♀️🙅🏻‍♀️🙅🏻‍♀️

Address: 177 Commercial St, Portland, ME 04101 (there are 3 locations in Portland, but this is the most central)

I don’t get it. I honestly don’t.

The Holy Donut is a donut shop that specializes in potato-based doughnuts. Their google reviews are off the charts. Every single travel blog says to come here and they say to come here first thing in the morning before they run out and have these doughnuts for breakfast. So we did. They open at 7am and we arrived just after 9am and there was a line of about 10 people in front of us, but the line went quick. We ordered 3 donuts (at $4.50 – $5 each): the blueberry glaze (most highly recommended), the blueberry lemon, and maple bacon. There was nowhere to sit so we ate it outside.

I was so excited to try these. After having a bite of each one… I was disappointed. I don’t get the hype. The potato-based doughnut made it really dense like a heavy cake and I felt like there was too much cake to the topping ratio so you get a small amount of flavour, then the rest of the time you have a mouthful of dry dense cake. Toby liked it, but he likes dense cake.

The aftermath was what made me curse this place. We hadn’t eaten anything apart from these donuts that morning (and I only ate a total of 2/3 of a donut to save room for lunch) but I started to have the worst acid reflux I’ve ever had (and I’m not a person that gets reflux issues!). Maybe it’s the empty stomach or the dense carbs in the donut, but after 40 mins of walking, I was sweating up a storm and vomited up acidic fluid multiple times (so glad I was able to find a restroom in time). Not appetizing, I know, but this messed up my stomach for the rest of the day which was quite upsetting because I was ramped up for more lobster meals in Portland. Never again shall I come here.

But, as much as I dislike this place, there are many more that love this place so I’ve included it in this post so you can make the judgement yourself. If you do go, I’d recommend not being on an empty stomach and bring some Tums or Pepto just in case. We struggled to find a pharmacy within walking distance.

3) Explore

We pretty much just ate and walked around town looking into the shops during our afternoon in Portland. Due to the donut incident, my stomach bothered me for the rest of the day so we didn’t do much else, but here’s a list of things I found that seemed cool for our trip next time:

• International Cryptozoology Museum (32 Resurgam Pl, Portland, ME 04102)
  • A small museum dedicated to the study of hidden or unknown animals. There are exhibits on Bigfoot, the Lochness monster, mermaids…etc. This is the only cryptozoology museum in the world.
  • This is a little out of town, so it’d be best to drive here.
• Victoria Mansion (109 Danforth St, Portland, ME 04101)
  • A 19th century mansion preserved to its original architecture from when it was built in the 1800s.
• Top of the East at The Westin Portland Harbourview hotel (15th floor, 157 High St, Portland, ME 04101)
  • This lounge serves cocktails with a view of Portland below.
• The Portland Observatory (138 Congress Street, Portland, ME)
  • A signalling tower that offers panoramic views of Portland and the harbor.
• Take a trolley tour
  • A fully narrated tour on a trolley that brings you around Portland and will also stop of Portland Head Light.
  • https://www.tripadvisor.com/AttractionProductReview-g40827-d26244845-Discover_Portland_City_and_Lighthouse_Tour-Portland_Maine.html
• Historical walking tour
  • https://www.mainehistory.org/education/walking-tours-1/
  • Self-guided freedom trail walking tour: https://www.mainehistory.org/documents/41/Portland_Freedom_Trail.pdf
• Go island-hopping on a ferry
  • https://www.cascobaylines.com/
• Take a lobster boat tour
  • https://www.luckycatch.com/
• Checking out local breweries
• Cape Elizabeth & Portland Head Light
  • The oldest and most well known lighthouse in Maine
  • Roughly 15 mins drive south of Portland

Some final thoughts

• I don’t get the hype with Holy Donuts.
• Portland is a cute town with tons of boutiques and cool shops.
• You only need a day to explore the city, but if you want to add on island-hopping, boat cruises, and museums, you can easily spend at least 2-3 days here.
• Try all the lobster rolls!

If you’ve been to Portland before, I’d love to hear about your favourite places or other places you’d recommend!

Need more travel recommendations for Maine? Check out these other places!