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15 Best Things to do in Portland, Maine

15 Best Things to do in Portland, Maine

As Portland’s food, beer, and overall tourism scene has exploded recently, it might seem overwhelming to decide which restaurants to check out, and activities to do while in town for a visit. Luckily, we recently spent a fair bit of time scoping all the best activities, scouring yelp, and taste testing everything we could share with you the best things to do in Portland, Maine! 

Here’s our list:

1. Eat like a Local at Eventide

Many of the best things to do in Portland, Maine involve eating and drinking. With so many options to choose from, it can be hard to narrow down where to eat, especially if you have to choose just one spot. That being said, Eventide was hands down our favorite low-key local joint, full of fresh, tangy seafood and delectable small plates.

They’re definitely known for their oysters, but don’t worry if you’re not a huge oyster fan. From Tuna Crudo, to their Greens Salad, everything else we tasted on the menu was tantalizingly tasty as well. We even had the best lobster roll to date here! Plus, if you head over at an off-peak hour (as we like to do), you can easily grab a seat at their cozy outdoor patio, which is a great place for lunch and gets lots of afternoon sunlight for you to soak in the rays.

2. 5 Lighthouse Bike Tour

If you’re planning your trip around gobbling up as many of these good Portland eats as we were, you’ll likely want a good way to burn off all those calories while doing some sightseeing. Enter the Portland 5 lighthouse bike tour. It offers an interesting and unique way for you to seamlessly leave the city and explore the coastal lighthouses, while learning more about greater Portland and its rich history. Tour groups are a small size (6-20 people),which feels more intimate than larger, traditional walking or bus tours. It runs from 9:30am to 3:30pm, so make sure you have plenty of time set aside if you want to do this!

3. Grab Breakfast with the lobstermen 

Becky’s Diner is a local joint that is a staple breakfast spot for lobstermen before they head out to a day of work on the water. They even offer packed lunches for lobstermen to take to their days at sea. So if you want to really join in on this experience, you can grab their classic lunch to go as a picnic, and sit on the shore to enjoy as you watch these same lobstermen out on the water! If you’d like to see it in full action, and get an authentic peek at this scene, be sure to head there extra early, from around 5-7am. Grabbing a bite here is without a doubt one of most unique things to do in Portland, Maine!

4. Explore Old Port 

Did you know that the city of Portland burned to the ground 3 times?! It was most recently rebuilt for the final time in 1908, this time entirely with brick, in an effort to curb any future catastrophic fires. If you take a walk around Old Port, you’ll notice that it appears frozen in time, mostly untouched since the last time it was built, with cobblestone interspersed streets and an almost European feel (think Old Port of Montreal vibes).

Make sure to take a walk down Exchange Street, and Moulton street for the best shops in town! Wander into some local shops or eateries (Like our favorite shop Seabags pictured above), and you’ll see they’ve largely preserved the original architecture. They have huge ceilings, massive front windows, and wide plank, old wooden floors that hold visible history in their well-trodden boards.  It’s also worth noting that downtown Portland, and Old Port especially, is astoundingly clean. We watched individual people walk down the street sweeping up anything stray garbage or leaves – not something you see in most cities!

5. Share some delectable bites at Central Provisions 

With all there is to see in Portland, you’ll surely work up an appetite. Whether you’re looking for a light dinner fare, or a small snack to keep your exploring going strong, check out  Central Provisions. They have a delicious menu of shared plates, full of fun flavors and unique combinations that will set your tastebuds alight. There are many plant-based options as well, so there’s sure to be something for everyone, and it’s a fun experience to order a bunch of different plates and share. Keep in mind, the plates really are small so if you’re starving, make sure you order a lot!

6. Check out Portland’s Working Waterfront 

The vibrant, working waterfront is something that makes Portland such a unique city, and one of the aspects that locals fight so hard to preserve. There has been careful consideration to avoid developing the working waterfront over the years, in order to protect the livelihood and legacy of local lobstermen, fishermen, and Portland itself. As you take a walk around to explore, you’ll see tons of lobster traps, fishing boats coming out and in, and smell those authentic wharf smells 😉

7. Eat a donut made from Maine Potatoes 

If you’re a fan of trying unique local delicacies, fresh seafood might be what’s first on your mind in Portland. However, you can’t miss tasting donuts made from Maine potatoes at Portland’s famous The Holy Donut. They’re perfect to grab and go while walking around town, or snag one of their limited bar seats by the big bay windows to people watch while you devour your donuts. This spot is definitely a must for anyone visiting Portland. Besides, where else can you say you ate a donut made from potatoes?!

8. Ride the Ferry to Nearby Islands 

Looking for a unique and affordable way to see the Portland harbor front and surrounding islands from the water? Hop aboard one of the Casco Bay ferries! There are lots of different ferries available, ranging from 2 to 7 hours roundtrip, and for many of them you’re free to hop off, and explore the islands as you please! We’d suggest taking the Mailboat to Great Diamond Island and stopping for lunch at Diamond’s Edge or even spending a night at the Inn at Diamond Cove.

9. Walk along the Eastern Promenade Trail 

Another one of the best things to do in Portland, Maine is explore the Eastern Promenade Trail. Approximately a mile walk from Old Port, and another mile in length itself, the Eastern Promenade Trail takes you on a peaceful stroll along the waterfront to the end of the East End of Portland. This used to be a less desirable part of town back in the day, as they were downwind from the fishy smell of the wharfs. However, it has recently become a vibrant and up and coming neighborhood due to its proximity to the ocean. You can walk, run, or even bike on the trail, and enjoy the views of sailboats drifting by.

10. Treat yourself to a swanky dinner at Bluefin 

After touring all over Portland, it’s definitely worth treating yourself to a nice dinner at Bluefin featuring fresh and local ingredients with a fun flair. The passionate chef, Gill Plaster, has created a menu that puts a unique spin on classic local seafood dishes, while still focusing on the freshest ingredients around. Here you’ll satisfy your Maine seafood craving in a less traditional and unique way, with dishes like Lobster S’cargot and Calamari fries. All of their pasta is made fresh in-house (a must!!), and they even make daily fresh small batches of custard-based ice cream, that has a crème brûlée base.

11. Become a lobsterman for a day

Curious about what goes on behind the scenes in the day of a lobsterman? There’s definitely no shortage of activities on the water in Portland, but one of the most unique ones is The Lucky Catch. This unique boat tour lasts about 90 minutes long, during which you’ll spend time out to sea with a group of other “first time lobstermen.” You’ll get the chance to learn all about different lobsters, their habits, and conservation efforts to keep the population high. You can even participate in hauling up the traps, or choose to sit back and take in the sights of lighthouses on the shore. At the end of the tour, you get the chance to purchase your lobster at the restaurant wholesale price (READ: a good deal). To top it all off, you can even take it across the street to the Portland Lobster Company where they’ll cook it up as part of a delicious dinner for you!

12. Eat dinner by a lighthouse

If you have a car available while you’re exploring Portland and are searching for a casual, outdoor, waterfront dining experience, definitely check out The Lobster Shack at Two Lights. With picnic tables galore filled to the brim with locals, it’s certainly not a white tablecloth experience. But, if you’re looking to take in the sunset over the ocean while you enjoy some tasty and fresh lobster bites, this place can’t be missed. As it’s a bit outside the city on Cape Elisabeth, it offers a more casual and low-key ambiance than anything you would find in downtown Portland. 

13. Take a guided Kayak tour 

With Fort Georges just off the coast and rugged islands all around, a kayak tour is a great way to explore the waterfront and the rest of Casco Bay in an up-close and intimate way. We’d highly suggest you do this with a tour, or at least a guide because it’s important you understand the ferry routes, as well as those of all the other ships in the vibrant, working waterfront we mentioned above. Huge cruise ships even come into port sometimes, which you definitely wouldn’t want to get in the way of! While in town, we heard horror stories of tourists putting their kayaks in on a foggy day and blocking traffic on the whole waterfront for hours because they didn’t take the right path, and nobody knew where they were.

14. Eat the best Molasses cookies of your life 

Even if you aren’t a fan of molasses, you need to try the molasses cookies at The Standard Baking Co. They’re not only delicious but also baked rich with history as Portland had a huge molasses import business back in the days of its thriving lumberyard. Portland would send ships of lumber to the West Indies, and because they didn’t want to send the ships back empty, they’d fill them with molasses. Eventually, this led to much of the molasses in town being turned into rum, leading to a town-wide drinking problem, and a local prohibition long before it was applied nationwide. The city still has speakeasies that you can imbibe in, and reminisce about the old days while you snack on a scrumptious molasses cookie.

15. Go for a sail

While it might seem like a pretty classic item to include, we just couldn’t conclude this list without encouraging you to get out on a sailboat while visiting Portland. There are tons of different charters to choose from, whether you want to do a day trip or a sunset cruise.

The list could go on and on, but we wanted to give you our essential and curated list to help plan your trip! If you’re heading to Portland for a long weekend, be sure to check out our 3 day itinerary here and let us know in the comments any questions you have!

Need a place to stay while you’re in Portland? Be sure to check out the Portland Harbor Hotel, where we stayed!




Saturday 6th of July 2019

Thanks for this great guide! I’m heading to Portland soon and will be using this blog post! -Caitlin


Monday 8th of July 2019

Yay!! So glad you loved it :) Would love to hear what you'd add to the list after your trip!

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