Not to be confused with the city in Oregon, Portland, Maine is one seriously underrated city. You can probably tell by the title where my focus is when it comes to the city, there are tons of historical sites, artistic wonders and more. It definitely has something for everyone. While 3 days in Portland Maine isn’t nearly enough time to see everything, it leaves plenty of time for adventuring. Whether you’re new to town or you’ve visited before, you won’t want to miss this 3 days in Portland Maine itinerary. I promise it’ll keep you busy!
RELATED: If this is your first time visiting, I recommend checking out my first timer tips for Portland!
3 Days in Portland Itinerary
As you dive into the city, you’ll quickly realize just how vast Portland really is. There’s lots of ground to cover so to make the most of your three days, you’ll want to try and arrive as early as you can.
Day One: Get Acquainted
I don’t know about you, but I like having a more relaxing first day to get familiar with a city. Luckily Portland is VERY walkable, especially in the downtown core. You’ll want to put on your walking shoes as there’s plenty of ground to cover! Depending on your arrival time, you can wander at your leisure… or I recommend hopping on The Real Portland Tour.
To be honest I’m not much of a tour person myself, but this is one you don’t want to miss. Derek, a local Portlandian, will show you the ins and outs of the city. With a Masters Degree in Library Science and a passion for storytelling, you’ll be mesmerized by the tales he’ll tell you. You’ll start with some general information like how tourism is the top industry in the state as it employs 1 in 6 Mainers. He’ll tell you all about the unique businesses like a hot dog factory turned hotel, the first chewing gum factory in the USA and more! Afterwards, you’ll drive into the beautiful Eastern Promenade where you’ll see gorgeous homes along with beautiful views.
No tour of Portland would be complete without visiting a lighthouse and with Derek you’ll visit THREE. On the way to South Portland, listen to the hilarious tale of the battle for the Whoopie pie and blueberry pie. You’ll come upon Fort William Park in Cape Elizabeth which was used through World War II and then turned into a park in 1962. If you’re lucky, you might just see the Bite into Maine food truck which features some of the tastiest lobster rolls in town. It’s also home to the most photographed lighthouse in the United States – the Portland Head Lighthouse. The third oldest in the USA, it was built in 1771. Take a stroll along the pathways and admire the gorgeous coastal views before hopping back in the van for your next destination.
Next on the docket is the Spring Point Ledge Lighthouse. This caisson-style lighthouse is the only one in the country that you can actually walk up to. It sits atop a dangerous ledge that juts out along Portland’s main shipping channel. Completed in March of 1897, it has since warned vessels and helped deter shipwrecks. While you won’t have time during the tour, you might want to revisit it as you can go inside and take a peek at its inner workings. If it’s not in the cards for you, check out their virtual tour. Don’t miss taking a peek at the remains of the old military fort known as Fort Preble before you head to your final stop.
You’ll round out your tour with a visit to the Portland Breakwater Light or ‘Bug Light‘. What you see is not actually the original lighthouse (it was wooden) but rather the second built in 1875. It’s made of curved cast-iron plates situate between Corinthian columns. Located within Bug Light Park, you’ll want to take a minute to explore as the park showcases some of the area’s shipbuilding efforts during World War II. Also if you’re a history buff, you’ll be happy to hear it was added to the National Register of Historic Places in 1973.
While each of the destinations on the tour are amazing in their own way, I can’t stress enough how much information Derek shares between them. Your head just might be spinning by the end of it. I kid you not, he’s an absolute fountain of information and an absolute pleasure to listen to. This is seriously an incredible tour of Portland so don’t hesitate to book yours! Tours generally last between 90-105 minutes and have a number of start times between 9:00am and 2:00pm.
INSIDER TIP: If you don’t have a car or are looking to take a break from your wheels, this is a great way to see the lighthouses without having to drive.
Now that you’ve got your bearings, I recommend exploring the downtown a little more. Take a stroll down Congress Street and peek into some of the local shops. Don’t forget to check out some of the gorgeous street art too! Make your way to the Old Port and Portland’s historic waterfront. You’ll be immediately enamoured with the cobblestone roads and red brick buildings that scream old New England! If you’re looking for the freshest fish in the city, head to the Harbor Fish Market. This is where a number of the restaurants get their eats so why not check out where the magic happens! Afterwards, Exchange Street is not to be missed. This is where you’ll find the famous Holy Donut (more on that later in this post) along with plenty of unique stores. Whether your wallet hates you by the end is up to you. 😉
You may want to grab a bite here or further north towards downtown. There is no shortage of amazing restaurants in Portland! Some of the fan favourites include Portland Lobster Co, Gilbert’s Chowder House and DiMillo’s on the Water. You can check out my suggestions for eats later on in this post.
Looking for a nightcap? Don’t miss visiting Vena’s Fizz House. This mixology bar and shop is super cute and eclectic. It started off as a mocktail bar but later got its license to serve adult beverages. There are so many great drinks to choose from with vodka, tequila, gin and more! If you visit during a themed week, you might even get the chance to try one of their unique concoctions. To be honest, I can’t remember what I had – all I remember is that it took some serious willpower to not drink it too fast! Don’t worry, they have non-alcoholic bevvies too. If you don’t have time to stay in for a drink, at least pop by to check out the space and grab one of their infusion jars as a souvenir.
Day Two: Brews & the East End
The sun is shining (hopefully), the birds are singing and it’s time to explore more of the city! Did you know Portland has the highest number of breweries per capita? That’s right, there are 17 breweries scattered between its 66,000 residents – and that’s not including their wineries and distilleries. That’s a lot of ground to cover in just one trip and tricky to do responsibly. Now if only you had someone to drive you around… say hello to the Maine Brew Bus!
Touring both locals and visitors around since 2012, this bright green bus will take you from A to B safely while giving you behind the scenes access at a number of establishments. There are over 20 different tours to choose throughout the week. Whether you’re thirsty on a Thursday night, want to enjoy some local beers and spirits on a Friday night or looking for a boozy weekend brunch, there’s a tour for you. Not a big beer drinker? There’s even a wine tour in the lineup (and it’s gluten-free!).
My experience with the Maine Brew Bus was nothing short of fantastic. Since I experienced it with in conjunction with the Women in Travel Summit, our tour was hand-crafted so we could get a taste of Portland’s craft beer, wine and distillery scenes. Our group of ladies hopped on the bus and made our way to our first destination – Foundation Brewing! Located in Industrial Park, it’s considered to be the birthplace of craft beer in Portland. This is where many breweries get their start and then move on to their own spaces once established. Consider it a sort of incubator for craft beers! They also do a lot of experimenting with their ‘wild beers’ by adding different yeasts and microbes. It’s a very cool spot with lots of great beer like ‘The Weekender’ which is a collaboration with Orono Brewing to help support Sebago Clean Waters.
Next, it was time to get a taste of Portland’s wine industry at Eighteen Twenty Wines. Now, this isn’t your usual winery as they actually make rhubarb wine. That’s right, you won’t find any grapes here! Though you wouldn’t know it as they taste very similar to a Sauvignon Blanc or a Pinot Gris. You have to try their Dottie Mae which is named after Amanda’s (the owner) grandmother. Why? It’s wild and sweet just like her. Eighteen Twenty Wines is absolutely adorable and a great stop on any tour.
Last but certainly not least was Hardshore Distillery, named 2017’s best craft distillery in America. We got a tour from the owner Jordan where he talked about the whole process from the grain grown on his family’s farm to how everything is done in house. They do everything as local as possible, including getting their water right from Sebago Lake. We enjoyed what I believe was dubbed their ‘Gint Mulep’ – 2 oz Hardshore Original Gin, 3/4 oz grapefruit, 1/2 oz lime juice, 1/2 oz grenadine and a spoon of honey garnished with mint leaves. I’m not a gin drinker by any means but this went down way too smoothly.
No matter what locations you go to, I know you’ll enjoy your tour. From hilarious guides to incredible stops, you can’t go wrong with a Maine Brew Bus tour!
By this point you should still have a decent amount of daylight left so I’d recommend heading east. Let’s walk off that buzz! Follow Congress Street as you pass by gorgeous architecture like that of Monument Square, Grace (church turned event venue), and Portland’s City Hall. You can easily spend hours just exploring the streets and admiring all of the gorgeous New England architecture.
INSIDER TIP: If you’re visiting in early May, chances are the cherry blossoms will be out. City Hall has cherry trees and are the perfect spot to enjoy these springtime flowers.
Head to the neighbourhoods of Munjoy Hill and the Eastern Promenade. Here you’ll find picturesque homes on quaint streets. It’s also home to the Portland Observatory, America’s last maritime signal tower. From late May until the middle of October, you can enjoy some stellar views towards Peak’s Island, Diamond Cove and Mackworth State Park. If you’d like to learn more about the area, check out this audio guide you can listen to as you explore.
If you start to get thirsty again, head to Washington Avenue and stop by Maine Mead Works. While you won’t find Vikings or monks here, you will find a number of delicious adult beverages. Enjoy a flight and learn about the process as they combine the magic of wildflower honey, water and their very own yeast strain. In collaboration with Dr Garth Cambray, a South African scholar, they’ve developed a continuous fermentation system that’s state-of-the-art to create beverages such as their HoneyMaker. They also have a number of seasonal meads as well as tasty concoctions like their lavender lemonade and habanero limeade!
Finish your night with some of the best views in the city, though you’ll have to work for it a little bit. Continue along Washington Avenue just past Maine Mead Works and hang a right on Marion Street. At the end of it you’ll see a pathway which leads to Fort Sumner Park. You might be huffing and puffing by the time you get to the top but you’ll be greeted to some seriously incredible views. Put your feet up and enjoy the colours as the sun disappears behind the horizon. If that trek worked up your appetite, head back down Washington Avenue to Duckfat Friteshack before calling it a night.
Day Three: Farewell Portland
By this point the days have probably flown by way too fast and you’re sad to leave Portland. I recommend drowning your sorrows with a visit to Holy Donut if you haven’t done so already – or even if you have. Take the time to peek around the Old Port and downtown if you haven’t had a chance to do so on your trip because this really is an area you don’t want to miss! If you’d like to see even more of Portland, you could hop on a bike tour around the Portland Peninsula and explore Back Cove, an area I wasn’t able to cover in this itinerary.
If you’re driving, this is a great opportunity to check out a few things outside of town before you leave. There are a number of great eats, breweries and more that lie on the outskirts of the city. If you’ve had enough of the city vibes, this is a great chance to enjoy some quality nature time. One great option is to hop on a ferry and tour Peak’s Island which you can also do as part of a group bike tour.
BUT did you know that there’s a waterfall in Portland? If you don’t believe me, head to the Nason’s Corner neighbourhood where you’ll find the Fore River Sanctuary. There’s a small parking lot at the end of Hillcrest Avenue where you’ll find a trailhead leading right to Jewell Falls. It’s the only naturally occurring waterfall within Portland’s city limits. That’s right, if there’s a waterfall to be found, this girl’s gonna sniff it out!
Additional Things to Do in Portland
Are you spending more than three days in Portland? Maybe the suggestions above didn’t quite tickle your fancy? You could quite possibly be like me and only have 36 hours in Portland and want to hear ALL your choices before deciding. I get it! Here are a few more things to do in Portland:
- Enjoy Some of Portland’s Coffee Shops – Like any big city, there are more cafes than you can shake a stick at. I highly recommend Yordprom Coffee (their hot Thai tea latte is awesome) or Speckled Axe (known for their cereal milk lattes).
- Hop on a Food Tour – Why not take a tour where you can eat along the way? Check out this culinary tour through the Old Port where you’ll stop at up to seven eateries as you learn about the history of the area.
- Or Just a Historic Walking Tour – If you’d rather save your eats for Portland’s restaurants, check out this historic walking tour which touches on railroads, fires, wars, famous poets and Hollywood producers.
- Fire Truck Tour – Why not add a little extra heat to your tour of Portland with a vintage fire truck tour! You’ll see historic sites, vibrant neighbourhoods and of course Portland’s scenic coast.
- Portland Museum of Art – With a focus on ‘art for all’, the PMA is dedicated to exhibitions/programs that reflect the diverse community in Portland while creating experiences with art to strengthen bonds within it. It’s free to visit from 4:00-8:00pm every Friday throughout the year.
- First Friday Art Walk – Visiting during the first Friday of the month? Enjoy free admission to a number of art galleries, museum and studios from 5:00-8:00pm.
- Hunt for Portland’s Speakeasys – There are two, Lincoln’s and Blyth & Burrows. Don’t bother asking the locals, they won’t help. You’ll have to do some sleuthing to figure out where they are!
- Try and Catch Some Lobster – That’s right, on a Lucky Catch Cruise you can try your hand at being a fisher(wo)man! Tour around Casco Bay as you hop from buoy to buoy hoping to catch a lobster or two.
Where to Eat in Portland
There are so many incredible restaurants and unfortunately my stomach only has so much room. I ate more than my weight more times than I can count! Since Portland was named the “Restaurant City of the Year” for 2018 by Bon Appetit, you know you’re in for a real treat. Here are my picks of restaurants in Portland you have to eat at!
Where to Eat Breakfast in Portland
It is the most important meal of the day, so why not start it with… lobster? Oh yes, I’m talking about the lobster omelette from Becky’s Diner. While it is on the pricier side, it is seriously to die for. I can’t recommend it enough and it’s just one of the unique was you can enjoy lobster while in Portland. Becky’s Diner is a spot where locals and visitors alike come to enjoy a meal. Whether you’re in a bit of a hurry or looking to sit down and enjoy, they’ve got you covered.
If you’re looking for something a little lighter, Higher Grounds in the heart of the old town is a perfect option. This forward-thinking coffee shop focuses on supporting locally-owned businesses from Maine. Serving Speckled Ax’s top-notch coffee, they also have a number of teas and delicious goodies. I highly recommend their morning bun. Higher Grounds also offers a number of CBD-infused items, botanicals and more… hence the ‘higher’ grounds. I didn’t get this reference until after I visited.
Best Restaurants in Portland for Lunch/Dinner
I’m not really much of a breakfast person so normally by lunchtime (and especially at dinner) I’m looking for some serious grub. You can’t go wrong at any of these restaurants.
Looking for a budget-friendly option? You can never go wrong with pizza, especially Otto’s Pizza. They have a number of locations around town including sit-down restaurants like in Munjoy Hill or a quick grab-and-go storefront in downtown Portland on Congress Street. They have options for every flavour profile and dietary restriction! As I was visiting during Portland’s Seaweed Week, I couldn’t resist trying their feature pizza. Who knew seaweed, avocado, cashews and onion could taste so good on a pizza!
What do tacos, pogos and whoopie pies have in common? You can indulge in them all at Highroller Lobster Co. While it started as a food cart it has since grown into one of the most sought-out destinations for lobster in the city. Their lobster and crab are always fresh and locally sourced and their brioche rolls are baked daily over at Southside Bakery. So Lindsay are you saying the tacos and pogos have lobster in them? Yes, it’s true and I can say from personal experience that both are incredibly tasty. If you don’t have room for dessert, be sure to take a Portland Cake Co Whoopie pie to go! And no, there’s no lobster in the Whoopie pie. That’s just gross.
One of the places I was told I had to eat at was J’s Oyster and I can see why. While you may have to line up for a table or rely on your reflexes to snag a seat at the bar, it’s 100% worth it. From a classic lobster dinner to shrimp scampi, there are dishes for lobster lovers, non-lobster yet seafood lovers and even those that prefer their meat not come from the ocean. I highly recommend some of their oyster (it is in their name after all!) and their seafood casserole is unreal. The dish may look small but it’s chock full of lobster, shrimp, scallops and crab meat in a rich butter and wine sauce… topped with more lobster. Yep, I’m drooling.
If you’re going to treat yourself, one of the best places to do so is at Bluefin. Situated within the Portland Harbor Hotel, Executive Chef Gil Plaster serves some of the best food I had the pleasure of enjoying during my time in Portland. Ingredients are locally sourced as much as possible, meaning your food will always be fresh. There are so many unique items that you can’t miss out on that you may have to visit more than once. I highly recommend their calamari fries, and lobster ‘scargot. Just thinking about them has me craving them hardcore. If only Portland wasn’t so far away from Kitchener!
Snacktime in Portland
Holy Donut is what you’ll be exclaiming after you take just one bite! In the heart of the Old Port is this delicious little shop serving tasty treats made from Maine potatoes. Yes that’s right – these are potato doughnuts. It may sound weird but I promise you they are incredibly delicious. With 16 flavours to choose from each day, I guarantee you’ll find a flavour to tickle your fancy. I couldn’t eat their margarita doughnut fast enough! My only regret is not getting more than one.
This walk-up fry window may not look like much but Duckfat Friteshack has some seriously delicious goodies. Enjoy the vibes of Oxbow Blending and Bottling’s beer garden while you chow down on their Belgian ‘Frites’ – fried in duck fat. These crispy critters are seriously delicious and are best enjoyed with one of their delicious dips. I recommend the truffle ketchup or curry mayo.
Getting to Portland Maine
As with any larger city, there are a number of ways to get to Portland. Whether you choose to fly, take the train or drive is up to you! Here are some details for each.
Flying to Portland Maine
While Portland is the largest city in the state of Maine, it doesn’t have a large airport. This means there aren’t a lot of direct flights so chances are you’re looking at some sort of layover. It’s my understanding that you can fly direct to and from Portland from the following cities:
- Atlanta, Georgia
- Baltimore, Maryland
- Charlotte, North Carolina
- Chicago, Illinois
- Detroit, Michigan
- Fort Myers, Florida
- New York City from both JFK and LaGuardia
- Newark, New Jersey
- Orlando, Florida
- Philadelphia, Pennsylvania
- Tampa, Florida
- Washington/Virginia from both Ronald Regan and Dulles International
Don’t see your city or area on this list? Take a look and see whether a direct flight is available from your destination using the widget below. If you can’t find one, there’s always the option to fly into Boston and then take the train from there!
Taking the Train to Portland
Speaking of Boston, taking the train from here to Portland is probably the most popular mode of transportation for visitors. Hop on the Amtrack Downeaster and say goodbye to Massachusetts because in 2.5 hours you’ll find yourself in Maine’s largest city! I haven’t done this myself as I’m slightly insane and opted to drive.
SOMETHING TO NOTE: Boston itself is a pretty rad city. You might want to extend your trip and check it out a little bit before heading to Portland. If you do, here are some of the great things to do in Boston!
Driving to Portland
Yes, I drove all the way from Kitchener, Ontario to Portland – a solid 1000+ km. What can I say? I love my road trips! While heading to Portland I had stops in Rochester, NY (thanks Megan!) and Hampshire County, MA, I straight shot the drive on the way back. Unless you’re used to long distances, I don’t recommend doing the full drive by yourself. I’ve driven 9 hours straight from Kitchener to Sault Ste Marie more times than I can count but this is next level. If I didn’t have my fantastic co-pilot Olivia to keep me alive and entertained, I would have struggled hardcore.
That being said, road trips are seriously amazing and I highly recommend it. There are so many places to stop that the journey to Portland could be a trip all on its own! If you’re thinking of exploring the state more or heading up the coast to Acadia National Park, I highly recommend having a set of wheels.
Where to Stay in Portland Maine
One thing that surprised me about Portland was how expensive the accommodation can be. It was still the shoulder season during my visit in early May, mind you my main reason for visiting was to attend a conference. My biggest tip for keeping accommodation costs low is to try and visit either mid-week or in the off-season before Portland gets busy.
I’ve got a few tricks up my sleeve to save some cash on where I sleep and I truly lucked out during my stay with an amazing Airbnb. There are honestly so many great listings in the area that it won’t take long to find a great spot to stay if you’re looking for affordable accommodation in Portland that has more space than a hotel. This fantastic apartment for ~$100/night is just blocks from tons of amazing restaurants and has a full kitchen, bathroom with bathtub, and more great amenities. If you’re looking for something a bit more bright and spacious, I’m definitely eyeing this chic one-bedroom apartment for my next stay!
However, if you’re looking to treat yourself (which we should all do more), you have to stay at the Portland Harbor Hotel. Located right in the heart of the old town, you have restaurants, bars, the waterfront and more at your fingertips. Plus with amenities like a complimentary bike rental and even a town car service, there really isn’t much more you could ask for! Don’t just take my word for it, see what others have to say about their stay or you can check out the full review of my experience. Book your stay at the Portland Harbor Hotel or take a look at the map of Portland below to see what additional hotels are available.
Ready to Explore Portland?
If you were ever wondering if Portland is worth visiting, the answer is a resounding yes! This is not a city to scoff at. Its sister city in Oregon may be more well-known but this east coast destination is not to be missed! What would be the first thing you’d check out from this 3 days in Portland itinerary? I know what mine is and it will always be LOBSTA.