If there was ever a city that resembles New England’s beauty and vigor, it’s Portland, Maine. If you can picture a bustling coastal city teeming with lush parks and Victorian architecture, then you might as well already be in Portland.
Aside from what you can expect in a city, some unique things make this city pop with life. In a day, there are plenty of things to see in Portland, Maine. For starters, how about the culinary delights found downtown or the picturesque lighthouses that dot the landscape?
For these reasons and more, Portland is easily one of my fave New England cities!
Get ready to learn about the ultimate day trip to Portland, Maine, with no detail left unsaid.
By the end, you’ll be planning your New England fall road trip and enjoying all the trip must-dos in Portland, Maine!
And hey! I’m giving you a map you can use on your trip too!
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Must-Know Things for the Ultimate Portland, ME Day Trip
Let’s cover all the nitty gritty details, from when to go to what to do in Portland, Maine.
How to Get Around for One Day in Portland, Maine
Although Portland is a very walkable city, there are some things to see that are just outside the central city!
I recommend having a car with you during your trip, as this can help save time on what is a very jam-packed day in Portland, Maine.
However, if you don’t have a car, here are some public services you can use to get around the city!
Metro—This is a bus service providing easy and reliable access throughout Portland. As you’ll only be in Portland for the day, it’s easiest to use cash to pay for rides. You’ll need the exact amount, so make sure you’ve got loose change. Each trip will cost between $1 and $4.
Bike Rentals—Bike rentals are another great way to get around the city. There are plenty of bike lanes in and around Portland, and most hotels rent out bikes you can use for the day.
Uber—Taking an Uber is a very reliable way to get around the city, but it’s also the most expensive mode of transportation. I would only recommend using an Uber as a last-ditch attempt to see everything on this list if you are running behind schedule.
Next Read: Learn how to become an Instagram influencer so you have the opportunity to travel to unique places like Portland.
Best Time to Visit Portland, Maine
This isn’t an easy question to answer, as each season in Portland has unique charms.
But if I have to pick, September to October is a wonderful time!
The trees in the streets and parks change from lush greens to vibrant shades of oranges and reds.
This makes the city a wonderland of color and something you’ll kick yourself for if you miss it.
Now let’s dive into the itinerary!
Insider Tip: Going in the fall means you can also head to Acadia National Park in the fall!
Your Day Trip to Portland, Maine
Arrive in Portland
Depending on where you are traveling from, you’ll want to try and get to the city around 7:30 am so you can settle into your hotel.
If you fly to Portland International Jetport, you’ll want to catch the earliest possible flight.
Another option is to fly or drive into the city the night before and settle in before an exciting day.
The aim is to start your day by 8 am, so you have plenty of time for all the best things to do in Portland, Maine.
Top Tip: If you are flying into Portland and need a car, use Rental Cars to find the best vehicle for you.
You’ll spend the morning exploring downtown Portland and all the lovely sights and museums in the area.
Breakfast + Coffee
Start your day right with a coffee in hand and a legendary donut from The Holy Donut.
The cafe opens at 7 am, so if you want a super early start to the day, you can go for it.
It’s best to go to The Holy Donuts on Commercial Street in downtown Portland, as it’s close to all the main morning attractions.
Since 2010, The Holy Donuts has been providing delicious potato donuts – yes, potato – to the Portland area.
It’s safe to say this is a fantastic way to get going, with over 35 original flavors like the savory bacon and cheddar or sweet pumpkin spice donut!
Pumpkin spice was my fave when Scott and I visited— just saying.
Portland City Hall and Merrill Auditorium
Now you’re all ready to start exploring, take a seven-minute walk to the dramatic Portland City Hall.
This is the governmental base for the city, and although this may not sound interesting, the architecture is simply stunning.
With its Renaissance revival style, this building from 1912 would feel right at home in the center of Rome.
Its tower reaches an incredible 200 feet in height, so it would be hard to miss this iconic building.
Another fantastic feature of this building is the Merrill Auditorium, which is an addition to the eastern wing of the City Hall.
It can seat a staggering 1,908 people and hosts many eye-catching performances each year. Aside from admiring the concert hall’s vast scale, you can gaze upon the Hermann Kotzschmar Memorial Organ.
Top Tip: If you plan on spending a couple of days in Portland, catch a showing at this extraordinary venue.
Wadsworth-Longfellow House and Longfellow Bookstore
The historic Wadsworth-Longfellow House is the next stop and only a five-minute walk from city hall.
You can travel back in time here and learn about four generations’ worth of history.
This three-story brick building sticks out amongst the more industrial buildings in the area.
Don’t for a second think this is just a building, though, as each of the four stories holds unique furniture relevant to every generation that lived in the house.
For over a century, this has been a Maine Historical Society landmark.
Entry tickets start at $15 per adult, including access to the secluded Longfellow Garden.
Before you think that’s all in one area, walk down the road to the Longfellow bookstore.
You can fulfill your book cravings here with a wide selection of new and old books for sale.
Portland Museum of Art
No more than a ten-minute walk from Longfellow books, the Portland Museum of Art – or PMA – is a must-visit.
PMA has a vast collection with over 18,000 pieces in their collection.
You may recognize some names that make up this collection, such as Andy Warhol or Claude Monet.
But some lesser-known artists contribute to the diversity that PMA represents, such as Yasuo Kuniyoshi and Eliot Porter.
You can easily spend hours exploring the showrooms of this breathtaking building.
For the sake of time, though, it’s best to look at the works you really want to see and then move on for the sake of time.
Entry tickets are $18 per adult, but you can get in for free if you are 21 or younger.
Top Tip: Visit the David. E Shaw and Family Sculpture Park to capture the perfect photo for Stories on Instagram.
The last of the things to do in downtown Portland, Maine, is to head over to the Victoria Mansion.
It’s a short 6-minute walk from PMA and is one of the stars of the city.
The traditional Victorian architecture paired with its distinct interior makes this building a national landmark everyone should visit.
With deep oak arches and royal red carpets throughout the house, you’ll feel as though you’re in the 19th century.
Top Tip: You can also see all the sights on this itinerary on a self-guided sightseeing audio tour.
Cathedral of the Immaculate Conception (Optional)
This is where a car or bike will come in handy, as they can cut a 20-minute walk down by half the time.
Crossing downtown and entering East Bayside, you’ll come across the Cathedral of the Immaculate Conception.
This is a church with one of the prettiest facades in the entire city. It’s the mother church of the Diocese of Portland, and it’s easy to see why.
The red and white brick facade with pointed slate roofs is simply breathtaking, and the interior is just as spectacular.
Inside you’ll find grand arches that create an otherworldly experience.
Both the interior and exterior of the building provide the perfect photo opportunity.
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Explore Portlands Kombucha Breweries (Optional)
Another food frenzy that’s shot up in popularity over the last decade is kombucha.
And with such a rich food culture in Portland, it’s no wonder you can find some of the top kombucha breweries here.
Take a five-minute bike ride or a ten-minute walk to the Root Wild Kombucha Brewery and discover how to make this unique drink.
You can indulge in truly unique flavors at the Root Wild tasting room, such as spiced apple, mint melody, or vanilla rooibos.
If you think that’s all, less than a minute’s ride away is the Urban Farm Fermentory and Gruit Brewing Co.
The flavors at this tasting room are just as crazy as at Root Wilds, with ghost chilli pepper, toasted oak, and Chaga chai, to name a few.
Overall, kombucha tasting is one of the fun things to do in Portland, Maine, that doesn’t require too much energy. This is a great activity for spending 3 days in Portland, Maine too.
By this stage, it will be somewhere around 1 pm.
It’s about time to fill up on delicious food before exploring the things to do near Portland, Maine!
Grab a Lobster Roll at the Highroller Lobster Co.
Travel back into downtown Portland and grab an unforgettable lobster roll from the Highroller Lobster Co.
There is nothing that screams Portland more than a lobster roll, and this restaurant is the best of the bunch.
Imagine snacking on a freshly baked brioche filled with tasty lobster, chopped romaine, and your choice of sauce.
The restaurant highly recommends the lemon and jalapeno mayo sauce, and for a good reason — the flavors pair perfectly.
Seriously, their rolls are so good I could eat about 20.
After a lovely lunch, you’ll be re-energized for a thrilling afternoon in Portland.
Fort Williams Park
Now it’s time to head across the Fore River out of downtown and into South Portland.
Take a 15-minute car drive to Fort Williams Park, a beautiful coastal oasis.
You’ll see all the top historical sights in the park, but you can start by enjoying the relaxing garden.
This space is brimming with color as well-kept flowers and plants make for the perfect sensory experience.
Portland Head Light
As you walk through Fort Williams Park, you’ll notice various signs pointing you to the Portland Head Light.
It’s best to visit each viewpoint in the park, as each one offers a unique view of this iconic landmark.
Built in 1897, the Portland Head Light is a crucial tool that helps boats and ships navigate their way through the treacherous Atlantic Ocean.
The lighthouse is still in use today, and when you stand close to this landmark, you get a true sense of the dangerous rocks below.
Insider Tip: Walk around the grassy areas and along the main sidewalk to get the best photos!
Fort Williams Batteries and Goddard Mansion
As you walk through the park, you’ll notice several buildings dotted along the coast.
These are battery stations to defend the city from coastal attacks.
Each battery in the park has a unique architectural style depending on its use.
Battery Keyes was one of the last to be built, and its impressive structure is a powerful sight.
While exploring the batteries, make sure you check out Goddard Mansion, now just a remnant of its lavish past.
Although you can’t walk through the ruins, getting up close still offers a fantastic photo opportunity.
Now it’s time to enjoy the best sun-kissed beach in town!
Take an 8-minute drive to Willard beach and enjoy a few calm moments before continuing your day.
The 4-acres of blissful beachfront provide mesmerizing views of Casco Bay.
You can also admire the surrounding islands, such as Fort Scammel, Cushing Island, and Peaks Island.
Fort Preble and Spring Point Ledge Lighthouse
After relaxing on the beach, take a 7-minute walk to Fort Preble, an old military base.
The building itself is incredible to walk through, as plants growing over the old concrete walls put you in an entirely new world.
No less than a minute’s walk away is the Spring Point Ledge Lighthouse.
The walk there is breathtaking as you pass over a narrow stone path.
It’s a small lighthouse, but the views are worth the quick walk.
Bug Light Park
Less than a 5-minute drive away is the last destination for the afternoon, Bug Light Park.
This is a lovely spot for an afternoon stroll.
Let’s not forget that you can see the famous Bug Light, a small lighthouse at Portland Harbor.
This is a lovely way to end an exciting day.
But remember, the night has just begun.
Dinner & Portland Evening Activities
After a lovely afternoon, there are several ways to enjoy the Portland nightlife.
Dinner Cruise Through Downtown Portland
Start your evening with a lovely sunset dinner cruise through downtown Portland.
With a delightful three-course meal and live piano music, there is no better way to take in the Portland skyline than on a cruise ship.
Bar Hopping at the Waterfront
The best place to go bar hopping is along Fore Street, with over 11 options close to one another.
One of the best bars to visit is the Luna Rooftop Bar, with fantastic views of Portland Harbor.
Another great option is Ri Ra Irish Pub, but the best thing to do is walk along the road and find the best spot for you.
Your Day Trip to Portland, Maine, at a Glance + Map
- Breakfast at Holy Donuts
- Portland City Hall and Merrill Auditorium
- Wadsworth-Longfellow House and Longfellow Bookstore
- Portland Museum of Art
- Victoria Mansion
- Cathedral of the Immaculate Conception (Optional)
- Explore Portlands Kombucha Breweries (Optional)
- Grab a lobster roll at the Highroller Lobster Co.
- Fort Williams Park
- Portland Head Light
- Fort Williams Batteries and Goddard Mansion
- Willard Beach
- Fort Preble and Spring Point Ledge Lighthouse
- Bug Light Park
- Dinner cruise through downtown Portland
- Bar hopping at the Waterfront
Where to Stay in Portland, Maine
With a bright and early start to your day, you’ll want to be as close as possible to the area with the Maine Portland attractions.
Downtown Portland is the best place to stay for quick access to everything.
Not only does downtown have some fantastic options, but it’s also the city’s cultural hub.
Below are three of my top recommendations that cater to everyone’s budget.
The Press Hotel—If you want the height of luxury, consider the Press Hotel, which is a part of the Autograph Collection. This 4-star hotel is in the heart of downtown Portland and is pet friendly. Each room has sophisticated finishings and unique touches, like a temporary art gallery that will make your stay unforgettable.
The West End Inn—Look at the lovely West End Inn for something in the mid-range level. This is another downtown accommodation that provides easy access to key sights, such as the Victorian Mansion, which is only 0.5 miles away. You can have a great time here with a delicious breakfast menu and themed dinner nights.
Inn at St John Portland in-Town—With a budget in mind, the Inn at St John Portland is a fantastic option. The old victorian style interior has a slight modern makeover, and it’s a pet-friendly establishment. This is an excellent option in downtown Portland, with great restaurants nearby, like Pizza Villa.
Final Thoughts on The Best Day Trip to Portland, Maine
Portland might not seem like it has much to offer, but this itinerary shows just how diverse and exciting a city it is. There are plenty of fantastic Portland, Maine, things to do that’ll leave you loving this city and wishing you could stay forever!
You won’t run out of things to see, with beautiful parks and countless historical landmarks. But hopefully, this day trip to Portland itinerary will help you enjoy all the best bits of this glorious city.
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