If you’re looking for a city with all the amenities — museums, bars, entertainment, the works — as well as beautiful coastal views and a whole lot of history, look no further than beautiful Portland, Maine!
While there’s a lot of talk about that other Portland, I submit that this Portland is jam-packed with everything that makes a city truly remarkable.
If it’s your first time visiting and you need help planning your trip, check out our 3-Day Portland, Maine Itinerary.
And while that is a great place to start, there’s so much to take in that just three days is going to leave you wanting more.
With plenty of cool places to stay and dozens of fun, educational, and delicious activities, you’ll be booking your next trip in no time. Keep reading to find out the 46 things in Portland, Maine you just can’t miss.
Riding on the Mailboat is one of my favorite summer things to do in Portland! You simply can’t beat being out on the ocean during a hot summer day.
The mailboat is exactly what it sounds like – a boat that delivers mail to the islands around Casco Bay. In addition to the mail, they also allow passengers to ride!
The route leaves from Portland and stops by 5 islands where anyone can get off to explore. Plan to stay on board for around 3 hours if you’re just in it for the ride.
If you decide to make a stop on one of the islands, make sure to know the other boats’ schedules so you can safely get back to Portland the same day.
**As of 8/26/21, the Mailboat Run is currently not accepting passengers due to COVID-19. Casco Bay Lines does offer other tours that are in operation, though. Check their website for the most up-to-date information.
2. Portland Head Light
I simply could not have a list of things to do in Portland, Maine without including the Portland Head Light!
This is reportedly the most photographed lighthouse in the world. Once you visit, you’ll see why!
The beautiful rocky cliffs, expansive view of the ocean, and rolling grassy hills make it an exquisite place to drink in the scenery of Maine.
Apart from the lighthouse, there are some lovely gardens to walk through that hug the cliffs, as well as many places to settle in for a picnic. There is even a lobster roll food truck available to grab some classic Maine lobster.
3. Have a Picnic
I love picnics. I think they’re the best way to truly enjoy the outdoors. Grab a good book, pack some yummy food, and pick a spot with great scenery, and you’re all set!
Thankfully there are plenty of locations that fit the picnic bill in Portland. Don’t forget to bring a blanket and/or sweatshirt – especially if you’re picnicking somewhere on the water. You never know when the ocean wind will pick up and make for a chilly time.
Don’t forget to bring along the necessary picnic essentials!
My top suggestions for a picnic in Portland are (click for GPS directions!):
Bug Light Park (My personal favorite)
4. Go For A Hike
There are plenty of places to take a nice, easy-going hike through the woods in the Portland area.
These are not hardcore mountainous hikes like you’ll find in Western and Northern Maine. However, they’ll still give you a decent workout!
Check out my list of 8 Easy Hikes In Portland, Maine for some awesome hiking ideas.
5. Brewery Hop
Portland has a seemingly infinite number of breweries that continue to increase each year. If you’re a beer lover, this is the place for you.
For a more in-depth look at what breweries are worth visiting, check out our Portland, Maine Brewery Guide.
If you’d rather hitch a ride, try booking a spot on one of the Maine Brews Cruise tours. They have bike tours, walking tours, a beer bus, and even boat tours!
6. Bug Light Park
There’s so much to see from Bug Light Park! Portland Harbor, Portland’s skyline, and the Bug Light Park Lighthouse (also known as the Portland Breakwater Light).
The lighthouse, by whichever name you prefer, only stands 26 feet tall. It was first built in 1855, but the wood took quite a beating, necessitating reconstruction in 1875.
This new version was designed by the same architect that designed the east and west wings of the US Capitol, as well as its iconic dome. To look at the lighthouse, it’s easy to see the Grecian influence with its Corinthian columns.
Beyond seeing the sights, you can go boating and salt-water fishing, or stay landside with a picnic.
7. First Friday Art Walk
No matter the weather, the first Friday of each month is dedicated to the arts in Portland!
From 5:00 to 8:00, you can enjoy a self-guided tour of the city’s galleries, studios, and museums, as well as take in live music in Congress Square Park.
Coffee shops, hotels, and even a meadery participate each month, with other pop-up venues and street vendors. Enjoy beautiful and creative jewelry, photography, prints, pottery, and more!
Make sure to check here for the next First Friday’s itinerary.
8. Go to a concert
Looking for a rocking good time? Portland attracts hundreds of popular musical acts a year to its convenient and spacious concert venues.
The indoor kids will like the large and historic State Theatre on Congress Street, complete with a full bar and snacks. It seats 1,900 people!
In terms of shows and festivals, though, it can accommodate as many as 5,000 people for views of both the river and that night’s performance.
For enlightening fun, don’t miss one of Portland’s many museums. Colonial history buffs should be sure to check out the Tate House Museum, which is the only publicly accessible pre-Revolutionary home in Greater Portland.
To educate and entertain kiddos, The Children’s Museum and Theatre of Maine is a must-do. Workshops, programs, summer camps, and exhibits — there’s plenty for the youngsters to discover!
Feeling artsy? The Portland Museum of Art boasts over 18,000 artworks in its collection, not to mention the outdoor sculpture park. They have an excellent collection of Winslow Homer’s works, who is widely regarded as one of the most influential American painters of the 1800’s. A fitting tribute to the painter who spent the last 27 years of his life just several miles away from the museum in Scarborough, producing iconic paintings of the tempestuous Maine coastline!
10. Peruse the Bookstores
Sometimes you just need to curl up with a good book. Portland’s independent bookstore scene is really something to behold.
A few of my favorites include:
Longfellow Books — a family-owned spot that features art by local artists and a dog-friendly atmosphere.
Quill Books and Beverage — you can grab a snack, a coffee, or a beer at this shop. For $25 and 24 hours’ notice, they’ll curate a surprise trio of books for you.
Bull Moose — looking for movies and music as well? Check out Bull Moose. There are even video games, tabletop games, and novelty items for sale. They are a small chain with a varied collection at each store, so stop in to more than one if you get the chance to see what gems they may have.
For an exhaustive list of bookstores we’ve already compiled in Portland, look here.
11. Shop around downtown
Is that credit card burning a hole in your wallet? Anything you could be looking for, you’ll find in Portland.
Take a walk around downtown and pack your car full of goodies.
12. Escape Room
Not just for corporate team-building exercises, escape rooms are a fun way for a small group of people to use their unique skills by solving clues together in an allotted amount of time.
The aptly named The Escape Room on Congress Street says it perfectly: “We’re the lock. You’re the key”. Each room is themed and has a different level of difficulty, from an 1860’s saloon to a serial killer’s basement.
A little further out in South Portland is Maine Escape Games. Reviews collectively call this one challenging, creative, and fun.
13. BYOB Paint Classes
Grab your brushes and the bubbly!
There are a handful of these ‘paint and sip’ studios in the area, including female-owned Muse PaintBar.
Don’t worry if you’ve never painted before: staff members guide you through the experience (and besides, a little drink doesn’t hurt the creative process!).
Another great location is Color Me Mine, close to Thompson’s Point. They even offer children’s classes!
14. Peaks Island
Peaks Island used to be regarded as the ‘Coney Island of Maine’, but these days it’s more of a charming island village than an amusement park.
Dine at the inn before walking the 3.7 mile loop around the island. Treat yourself to ice cream at Down Front afterward.
15. Gilsland Farm
If you’d like to take advantage of a beautiful day, head to the Gilsland Farm Audubon Center.
The sanctuary is open all year with a variety of flora and fauna to discover. There are also multiple trails, so you can take a short hike or traverse the entire center.
If you’re visiting in June, make sure your camera is ready for the peony garden!
At one time there were over 200 varieties of peony planted on the property, but time has reduced the garden to a small, yet gorgeous, collection close to the headquarters building.
16. Visit the LL Bean Headquarters in Freeport
That’s one BIG boot! Open 24 hours a day, you can visit the 16.5 foot tall all-weather LL Bean boot at any hour.
The flagship store was opened in 1917 by avid huntsman Leon Leonwood Bean who once said that famous boot would clock in at a size 410.
The headquarters has multiple levels full of all your outdoor and camping needs, in addition to numerous impressive taxidermied animals.
There’s also a 24-foot long Riverbed Aquarium inhabited by trout and salmon sourced from Maine hatcheries.
And if you want some great LL Bean gear without the high price tags, the LL Bean Outlet store is just down the supply amazing bargains.
17. Candlepin Bowling
For some retro New England fun, try your hand at candlepin bowling.
Unlike tenpin bowling, the pins are thin and shaped like…well, candles. The ball is much smaller with no finger holes, and fallen pins (known as ‘dead wood’) are not cleared between rolls in a frame.
There are a few more differences between candlepin and tenpin bowling, but I feel candlepin bowling is best summed up here: “Candlepin is full of heartbreak and poetry and luck. The pins dance and dodge. Sometimes they fall over when you least expect it. Sometimes they persevere.”
Just outside of Portland proper sits Westport Bowling Lanes, a classic candlepin bowling alley complete with ‘60s decor and self-scoring.
18. Farmers Market
Is there anything quite like visiting the farmers market early in the morning, coffee in hand, perusing the stalls piled high with local produce?
From 7 am to 1 pm on Wednesdays and Saturdays in Deering Oaks Park, you can shop for fruits, vegetables, all sorts of cheeses – even oysters!
Once you have your seasonally appropriate wares in hand, you can check out the splash pad, playground, ball diamond, and beautiful walking trails of the park. We love to take advantage of the tennis courts and sand volleyball courts!
19. Flea For All
On the hunt for something vintage, hard to find, or one of a kind? Check out Flea For All.
I love to frequent this spacious (we’re talking 10,000 square feet of curated merchandise!) and delightfully interesting store on a free afternoon with an open mind. You never know what you’ll walk away with.
These people really take pride in curating and displaying a diverse array of collectibles. The furniture selection alone fuels dreams of a total house redecoration. There are vintage vinyls for days, not to mention an extensive and eclectic art collection.
Pro-tip: Shop early on Friday. They’re currently only open Friday and Saturdays, and you may risk losing out on some truly spectacular items if you wait until Saturday.
20. Visit a speakeasy
Though Prohibition is long over, the allure of drinking a cocktail by candlelight, tucked in a secret corner of a city with friends or lovers, is irresistible.
Lincoln’s on Market Street scratches that clandestine itch, with its hidden entrance, underground locale, and dimly-lit, intimate lounging areas. The drinks are only $5 and remember to stop at the ATM beforehand because they are a cash only institution.
If you require a snack during your subterranean exploits, follow the candles and stained glass through the brick-lined tunnel down to Bramhall. Along with a full bar, they also offer a menu that includes ricotta agnolotti and strip steak.
21. Eat in an authentic diner car
You can’t visit the city and ignore Miss Portland. You’d simply be missing out because breakfast or lunch on your Portland trip isn’t complete unless it’s enjoyed in a retro setting. Don’t worry, this isn’t the typical gaudy, black-and-white tiled, brightly lit jukebox-equipped 50’s diner that comes to mind. This place is understatedly cool with a simple, clean look to highlight the authentic 1949 Worcester Lunch Car that the restaurant is built around.
What’s on the menu? Miss Portland serves fat pancakes, crispy bacon, and specialty flatbreads (just to name a few) for breakfast and classic burgers, fries, and rich milkshakes later in the day.
The historic lunch car is replete with blue leather stools lining the lunch counter, stainless steel starburst panels, and a daily specials board.
Just remember: “There is nothin’ finer than a Worcester Diner”. She’s open daily from 8 am to 2:30 pm.
For other breakfast suggestions in the area, check out our list of The 5 Best Breakfast Restaurants in Portland.
22. See a show
For an intimate setting to take in a show, you can enjoy musical, theatrical, or comedic acts at One Longfellow Square. Self-described as Portland’s Listening Room, the non-profit venue is charming and warm, and eager to invite patrons back this fall.
Another great option is donation-based Blue on Congress Street. This cozy spot has been named Portland’s best jazz venue for several years running, and they dedicate their Saturday nights to jazz acts.
Since they are donation-based (with those funds going to the musicians), please keep in mind their one purchase minimum of food/beverage in order to keep this gem running! Make sure you stop by the ATM beforehand.
23. Grab A Coffee
It may seem every other storefront is a coffee shop, but not all coffee is created equal!
Don’t pass over Speckled Ax, who wood-roasts their coffee beans using a vintage Italian Petroncini. The wood fire not only imparts smokiness to the beans but also preserves more of the coffee’s natural oils, leading to a truly spectacular coffee-drinking experience.
For a delightfully airy atmosphere close to an urban park, check out Bard Coffee on Middle Street. As one recent Google reviewer wrote, “this is what coffee is supposed to taste like”.
24. Lobster Boat Tour
The first thing that comes to many people’s minds when thinking about Maine is lobster. Lobster rolls, lobster bisque, a classic lobster bake…the list goes on.
If you’re interested in seeing where all that lobster comes from, book yourself a lobster boat tour. There are at least two that leave from Portland Harbor close to the ferry terminal:
Lucky Catch Cruises: Tours run right about an hour and a half, and you can choose between a Portland Headlight tour or a seal watch tour.
In July and August, they also offer the Whitehead Passage Lobstering Cruise, which passes by White Head Cliff and a multitude of forts and lighthouses. On any one of the cruises, not only will you encounter lobsters but also other sea creatures and birds.
Rocky Bottom Fisheries: In addition to lobstering tours, Rocky Bottom also offers BYOB sunset cruises through Casco Bay. This would be a fun way to kick off a bachelor or bachelorette party, with the option to add on lobster rolls for the party.
25. Go Sea Kayaking
There are so many opportunities to take advantage of the stunning waterways around Portland, including sea kayaking.
Whether for just a couple of hours, half days, and even full-day excursions, there are a variety of tours available to paddle along the coast and out into the bay.
Expect to see coastal wildlife, lighthouses, and stunning, water views. You can also do a sunset tour, which is probably one of my favorites.
26. Bike The Eastern Trail
Over 65 miles of connected on and off-road segments make up the Eastern Trail, which starts at Bug Light and goes all the way to Portsmouth, New Hampshire.
There are at least 22 miles’ worth of off-road biking trails in and around Portland proper. It’s a great opportunity for some scenic exercise!
My favorite place to experience The Eastern Trail is about 15 minutes outside of Portland in Scarborough. Click here for directions to the parking area. Head south to ride through an amazingly beautiful marsh!
27. Catch A Movie
What’s better than kicking back with some popcorn for a flick? Patriot Cinemas shows the latest movies as well as some indie films. On a budget? Go on a Tuesday when movies are $5.
For a more cultured evening, the Portland Museum of Art offers a cinema experience in their Bernard Osher Foundation Auditorium.
28. Paint Your Own Pottery
Just like the BYOB painting classes mentioned above, you don’t need to be an artiste to get in on the pottery-painting fun.
Color Me Mine offers classes on painting your own pottery in addition to the sip-and-paint classes. I like to get together with some friends at these classes and see how each of us approaches our clay pieces differently!
29. Visit Some Distilleries
If you’re interested in peeking behind the curtain to see how some of your favorite spirits are made, take a distillery tour.
There are several distilleries in Portland to choose from, like Maine Craft Distilling. They’re the makers of some pretty creative canned cocktails, such as a Blueshine Lemonade and the Italiano Orange Spritz, which you can even find at local grocery stores if you want to take some home with you.
Hardshore Distilling came onto the scene in 2016 with their flagship Hardshore Original Gin. Their tasting room on Washington Avenue is open daily.
For a little more variety — liquor, beer, wine, and food — try out Liquid Riot Bottling Company with its waterfront deck.
30. Go On A Trolley Tour
For another opportunity to have some fun while learning a lot, take a trolley tour. On Portland Discovery’s City and Lighthouse tour, you’ll take 105 minutes to visit the Portland Head Light, as well as the Victoria Mansion and Old Port.
Portland Discovery even offers a combo package that’s part trolley and part boat tour to really maximize your Portland learning experience!
31. Book A Foodie Tour
We’ve all got to eat, and one of the most fun ways to see the city and try out a lot of different cuisines at once is by taking a foodie tour.
Food tours are usually a few hours long and occur regardless of the weather. You’ll also want to wear comfortable shoes, as they are usually walking tours.
There are a few different tours available through Maine Foodie Tours, including a seafood lover’s tour and one that highlights both the culinary and art worlds.
I’m really looking forward to trying out the Maine Lobster Picnic and Portland Harbor Cruise, which is part-walking, part-Elizabeth Grace – a 33-foot boat that launches from the Old Port!
32. Kotzschmar Organ
Okay, so this is pretty cool and entirely unique to Portland. The Kotzschmar Organ is an enormous, absolutely gorgeous instrument with over 7,000 pipes.
It’s one of the only ones in the world, with its organ chamber large enough to hold SIX tractor trailers!
Thanks to the preservation efforts of the Friends of the Kotzschmar Organ, it is still in use today. You can go see this behemoth for yourself by touring its inner workings or attending a concert.
And don’t worry: one of the yearly concerts is, of course, The Phantom of the Opera.
33. Wine And Food Pairing Sail
While not all of us can afford to own a boat or fortunate enough to have friends in Portland with one (*cough* time to step it up all of my Portland friends reading this), sailing out to the ocean with a glass of bubbly in one hand and fine fare in the other doesn’t have to be out of reach.
Wine Wise offers themed cruises such as Orange and Rosé Wines or Sicilian wines along with delicious food pairings. They’ll even occasionally offer a Chef Series midday sail, with a sommelier and guest chef to make it a truly memorable afternoon.
I can’t think of much else better than sea spray, a glass of wine, and delectable cuisine with friends!
34. Maine Ninja Warrior Gym
Now this is for someone a lot braver and faster on their feet than me! I’ve never seen a gym quite like the Maine Ninja Warrior Gym in South Portland.
Their tagline, ‘Rethink the Way You Exercise’, is exactly right: there are parkour courses, challenging climbing walls, and impressive obstacles.
The Obstacle Course Style training focuses on equipping serious contenders with the skills they need to compete on the show American Ninja Warrior (hint: not me).
35. Southworth Planetarium
This is a lot more my speed! The Southworth Planetarium is for curious minds and folks full of wonder about the world around us.
They have such shows as Dinosaurs at Dusk! (not just for kid!), Into the Deep – an exploration of the depths of the ocean – as well as the history of marine biology and underwater geology. It’s a wonderful family activity.
36. The Axe Pit
Safety is the number one priority of staff at The Axe Pit, a social axe-throwing facility for people who think bowling is lame, but still like tossing things down lanes in a competitive fashion.
On their FAQ page, they explicitly say that you are neither too weak nor too old to throw an axe — they weigh between half a pound and one-and-a-half pounds, so this place is really open to anyone*!
You can even enter tournaments with cash prizes! So what are you waiting for — get throwin’!
*18 and older or 13+ with a parent.
37. Whale Watching
It’s remarkable that a city as modern and bustling as Portland can also offer whale watching — it’s not just for remote Alaskan outposts.
Sailing out into the bay on a three-and-a-half-hour tour with Odyssey Whale Watch, it’s possible to spot all sorts of wildlife. The knowledgeable and friendly staff will talk you through the marine surroundings and any animals you might come upon.
Sea turtles, sharks, dolphins, and of course humpback, minke, and finback whales could all make an appearance on your journey!
Have the camera ready and be prepared to get a little wet; once you’re on the boat, you’re in the splash zone!
38. Go To A Game
Portland has a few home teams that we root for here, and I hope you will too if you go to one of their games!
Our baseball team, the Portland Sea Dogs, calls Hadlock Field home. You can check out this season’s schedule here.
If hockey is more your thing, the Maine Mariners play at the Cross Insurance Arena.
To benefit the Good Shepherd Food Bank, the Mariners have partnered with Backyard Farms and Portland Pie Company in a yearly tomato-throwing contest at the arena. Toss a Tomato, Win Some Dough! is a fun way to help out a great organization (with the chance to win some cash!).
The Maine Celtics (formerly known as the Maine Red Claws) are the local NBA G League basketball team. Their new green lobster mascot will lead opening ceremonies in November.
39. Go On a Hovercraft
Have you ever been on a hovercraft before? I’m going to go out on a limb here and say probably not.
When you visit Portland, though, there’s a place for you to give it a try! Hovercraft Maine offers hour-long tours through Casco Bay.
There, you’ll see the mansions of Foreside and pass through the Royal River Estuary, an open salt marsh. From there, you’ll hug the shores of Long and Peaks Islands each, before swinging past Portland Head Light on the way back to harbor.
Interested in how hovercrafts work? Check this out.
40. Pedal Party Boat
I hope you’re nowhere close to sick of Casco Bay because there is still plenty to do there, including renting a pedal party boat with up to nine of your closest friends!
BayCycle Cruises is an hour and a half long ride (er, pedal) with the option to bring your own libation or add the Brews Cruise ticket to have three beers per person provided.
This is a fun way to drink on the water while also watching for seals and other Maine wildlife.
41. Float Harder
For an indoor water-based experience, check out the relaxation spa Float Harder on Washington Avenue.
Whether you choose to relax in one of the float pods or float rooms (more on the difference in a moment), the water is heavily salinated in order to float your body in 94-degree water for ultimate ‘me time’.
The pods are seven-foot-long domed tanks with a lid, so as you float within it, you’re shut off from the world (and cold air!). The rooms, on the other hand, have high ceilings — like stepping into a shower/tub combo — and a door to shut behind, rather than atop of, you.
Keeping with the relaxation theme, this luxurious and truly zen SpaLounge offers a variety of aromatic soaks as well as aromatherapy massage to heal and rejuvenate your body.
There are plenty of products to take home as well, to cleanse and nourish at home. Choose from a variety of teas and teaware accessories, CBD products, and beautiful bath sets.
43. Spa Day
If you need one more opportunity to really chill out, treat yourself to a day at the spa. Nine Stones Spa is right in Old Port.
They believe that self-care isn’t an indulgence but a necessity, and I couldn’t agree more. Get a massage, a facial, a touch-up to your nails — you name it — all in a beautifully appointed, restful atmosphere.
Another, perhaps even more glamorous option, is Akari Salon and Spa. The crystal chandelier hanging from the high ceiling really sets the tone for a fabulous experience.
Treat yourself to their Signature Spa Day, which includes a luxurious massage, facial, mani/pedi, and a blowout, with lunch in between.
44. Portland Observatory
“Historic character enriches our lives” is the tagline at the Portland Observatory – the last standing maritime signal station to date back to the Golden Age of Sail in the 1800’s.
The octagonal building stands 86 feet high and was originally built to communicate with Portland’s harbor.
Today, after years of restoration, you can embark on a 75-90 minutes walking tour with a guide, who will also show you historically relevant (and interesting!) facets of the neighborhood located in the west side of the city.
The observatory was designated a National Historic Landmark in 2006 and is maintained by the local historic preservation non-profit, Greater Portland Landmarks.
45. Maine Duck Tour
Here is another unique way to explore both the land and sea of Portland: a duck boat!
These amphibious vehicles and their informative and funny crew will take you around the city (routes vary but all include fascinating landmarks) before driving right into Casco Bay!
This is a great activity for the whole family. Get your tickets for the 60-minute ride early, as they sell out fast.
46. Walking Tour
Along with the food tours, boat tours, trolley tours, and even the duck boat tours, sometimes you just want to take a good ol’ fashioned walking tour. Portland has them in spades.
The keys to successful walking tours include a fascinating area (check), and an educated, humorous tour guide.
You’ll find that with Portland Maine Walking Tours, where you’ll walk with a knowledgeable and funny guide to more than a dozen destinations. You can choose between a couple of different routes depending on your stamina and interests.