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Are you planning a visit to Portland, Maine? Lucky you! Situated on the southern coastline of Maine, this vibrant port city is absolutely gorgeous. It’s actually the biggest city in Maine with a population of about 68,000, although that’s perhaps not saying a whole lot in a state known for its small towns!
This Casco Bay gem holds so much interesting New England port history and is still a popular place to live and visit to this day. There are many fun and unique things to do in Portland Maine, both for history buffs and modern adventurers!
Whether you’re seeking out cultural experiences and historical landmarks, or you’d rather fill your Portland, Maine bucket list with exciting activities on land and sea, there’s truly something for everyone.
When is the best time to visit Portland Maine?
If you are planning your Portland getaway, you may be wondering which time of year to choose? In most of coastal New England, summer is the peak time for visitors.
Portland’s proximity to many nearby beaches means summer is when the city is busiest.
But people love fall in Portland, too, so September and October are gorgeous months to visit.
But you can avoid the crowds and have Portland slightly more to yourself if you visit outside of these peak times. For example, Portland is recommended as one of the top places to visit in May in the US, and I quite agree.
With warmth seeping in, the days growing longer, and plants and trees in bloom, May is stunning in Portland.
Things to Do in Portland Maine
Explore Old Port
With its cobblestone streets and historic red brick buildings, this area of Portland, Maine has been beautifully preserved. Don’t think for a moment that it’s just historic sites to visit, however, because this is one of the most bustling tourist areas in the city!
You’ll find so many great boutique shops, fantastic restaurants, cool bars, and cafes. Swing by Old Port Candy Co or the Holy Donut to satisfy your sweet tooth as you stroll around Old Port. Holy Donut uses a rather unique ingredient to create their delectable doughnuts, and this is one of only four locations in the state.
PS if you join this Old Port Donut Tasting Walking Tour, you get to skip the line at Holy Donut!!!
Old Port is fun to just walk around and sight see, especially while wandering Commercial Street where you can catch a glimpse of the always hard working waterfront!
In fact, if you’re looking for things to do in Portland, Maine in early June, you might be able to catch the Walk the Working Waterfront event. This interactive downtown Portland ME event encourages visitors to explore the many working piers and wharves and celebrate this city’s vibrant maritime culture and history.
Old Port is definitely one of the most popular places to visit in Portland Maine, so be sure this is on the itinerary, whether you’re in town for just one day or more.
Oh, and a great way to get a “taste” of Old Port is to sign up for a tasting tour like this Old Port Culinary Walking Tour that walks you through some of the must visit spots in the neighborhood. Yum!
Tour the Lovely Victoria Mansion
Did you know that this beautiful National Historic Landmark was almost torn down to become a gas station?? Egads, I know!
Luckily for all of us, Victoria Mansion was saved and the ongoing restoration and renovation of this significant architectural icon has been absolutely magnificent. Today, you’ll find that the these efforts have yielded grand results with about 90% of the original woodwork, finishings, paintings, and brownstone having been maintained.
You can visit Victoria Mansion for yourself from May to October, but be aware that tours are limited and reservations are highly recommended. You can find more info about tickets to Victoria Mansion in Portland here.
Go on a Portland Lighthouse Tour
Okay, so there technically aren’t any lighthouses in Portland proper, but there are several nearby! And when we say nearby, we mean nearby, with six lighthouses less than a twenty minute drive from the city.
First and most recognizable by most is the Portland Head Light, often referred to as the “most photographed lighthouse in the world.”
You’ve seen it before, right? Maybe on a postcard or a thumbnail image for Maine’s coast?
Of course, the Portland Head Lighthouse is very scenic with the way it sits so stately on the rocky outcropping, but there are other lovely lighthouses near Portland, Maine, too!
You’ve got the Bug Light (Portland Breakwater Lighthouse) that sits on the South Portland side of the Fore River, the Spring Point Ledge Lighthouse in South Portland, Cape Elizabeth Light at Two Lights, and more!
The easiest way to really get a good look at these Portland area lighthouses is by taking a lighthouse tour! You’ve got some great options, too.
This highly rated Portland lighthouse tour is called the Best of Maine Lighthouse Scenic Cruise, and is provided by Portland Discovery Land & Sea Tours. At 105 minutes, this narrated tour is the perfect amount of time to cruise Casco Bay and learn a little more about the history of Portland Harbor and the lighthouses and the Civil War era forts you will pass by.
You could also opt for this popular Sunset Lighthouse Cruise in Casco Bay with Drinks, given by SeaPortland. With 1.5 hours of lighthouses, local craft brews, and sunset views, it’s no wonder this is one of the most popular lighthouse tours in Portland!
If you’d prefer to view the lighthouses by land, that’s always an option too! This very highly rated guided lighthouse tour with Portland Explorer includes a tour of downtown Portland, as well.
Climb to the Top of the Portland Observatory
The Portland Observatory is a National Historic Landmark was once an important communication tower for the city. It was used to look for ships as they approached the port so local merchants could be signaled to get ready to receive.
Of course, once two way radios were invented, this became unnecessary and the future of this tower became uncertain.
Luckily, the Portland Observatory was opened for public tours and now everyone willing to walk up its 103 steps can enjoy the expansive 360 degree view of the city of the Portland, Maine!
Explore the Arts District
Are you looking for art and culture during your Portland visit? You’ll love the Arts District, home to a variety of brilliant museums, art galleries, cafes, and more that are perfect for art lovers of all kinds.
The Portland Museum of Art is a must visit, with a diverse collection that includes contemporary, historic, and iconic works created by artists from Maine and beyond.
Also located in the Arts District is the Maine College of Arts & Design, where you can scope out exhibits at the Institute of Contemporary Art (ICA) at MECA&D and the June Fitzpatrick Gallery
Ever heard of the Portland Maine art walk? MECA&D plays a significant role in this cool art event!
On the first Friday of every month, Creative Portland holds the First Friday Art Walk in the Portland Arts District. Be sure to check it out if you are in the area on the first Friday of the month!
Sample Craft Brews at Local Portland Breweries
If you’re looking for Portland breweries, you’ve got some incredible choices! With over 25 breweries in the Greater Portland area, there’s something for just about everyone.
You’ve got brands that are recognizable all across the United States, like Allagash Brewing Company, and ones that might be completely new to you, like Foulmouthed Brewing in South Portland, which is also a popular local brewpub.
If you visit Allagash Brewery in Portland, you’ll find yourself on Industrial Way, an area that is home to several popular Portland ME breweries, like Battery Steele Brewing, Foundation Brewing, and many more. There are always fantastic food trucks in this area, too!
Read Next: 15 Best Breweries in Portland Maine: Breweries to Visit ASAP
Explore Casco Bay Islands
The Islands of Casco Bay include Chebeague Island, Great Diamond Island, Peaks Island, Long Island, and more. If you’re looking for an easy day trip, consider hopping on Casco Bay Lines for Peaks Island. With over a dozen daily trips between Peaks Island and Portland proper during the busy summer months, there’s plenty of opportunity to explore!
Hop on a Peaks Island tour via golf cart once you arrive to learn about the history and current culture on this Casco Bay Island. Peaks Island is home to great restaurants, beautiful natural attractions, and interesting museums like the quirky Umbrella Cover Museum!
You can also hop on a Harbor Lights & Sights Cruise for the opportunity to pass by House Island, Cushing Island, Peaks Island, Little and Great Diamond Islands, and Diamond Pass.
You’ll also see Portland lighthouses, Civil War era Fort Gorges, and even a popular seal watching spot called Halfway Rock.
Take a Portland Trolley Tour
The Peek at Portland Sightseeing Trolley Tour is a sixty minute, fully narrated tour of some of the most popular Portland, Maine attractions.
You’ll get to drive by the lovely Victoria Mansion, the Portland Observatory, the Portland Museum of Art, The Wadsworth-Longfellow House, and the Eastern Promenade, so if it’s your first time visiting Portland, this could be a great way to get the lay of the land.
Plus, isn’t riding in an open air trolley always just kind of cool?
Catch a Show at Thompson’s Point
One of the coolest music waterfront music venues in New England, The Depot Pavilion at Thompson’s Point has hosted all kinds of artists over the years, including big acts like Bob Dylan and The Lumineers.
If you’re looking for things to do in Portland Maine in summer, check out the The Thompson’s Point calendar to see who’s out on the lawn during your Portland visit. Don’t forget to bring a low lawn chair or blanket to spread out on!
Scope Out the International Cryptozoology Museum
The International Cryptozoology Museum is a must visit for those with an interest in some of the more rare, one of a kind scientific and zoological specimens.
For those who don’t know – as I didn’t before learning about this interesting place – cryptozoology is the study of hidden animals such as yeti, bigfoot, etc. Among the unique exhibits at this Portland museum are hair samples from an alleged Bigfoot encounter.
I think most of us know (or perhaps we are ourselves) someone who would lose their mind at the prospect of exploring and studying collected articles of “evidence” of these elusive creatures. If this sounds like you or your fellow traveler, you’ll certainly want to add this to your Portland things to do list!
Visit the Historic Wadsworth-Longfellow House
Open to the public June through October, the Wadsworth-Longfellow House is where literary great Henry Wadsworth-Longfellow was raised as a young boy. It is also a significant New England architectural artifact as it is the oldest standing brick structure on the Portland peninsula!
Impress Your Inner Foodie with Portland Restaurants
If you haven’t already heard, Portland ME is a bit of a foodie destination! Of course, you’re going to find phenomenal fresh caught seafood at many restaurants in this coastal town, but there’s a decent amount of diversity in Portland restaurants, as well.
For brunch, you’ve got to try Hot Suppa Southern Kitchen & Bar. Their corned beef hash has received rave reviews from Bon Appetit Magazine, and as one of our favorite Maine experts Justin Smulski stated in his Portland restaurant round up, “Hot Suppa is the kind of restaurant telling you to move to Portland, not just visit.”
Most visitors to coastal Maine are in search of fresh caught seafood, and that’s not difficult to find! Looking for the full oyster bar experience? Scales and Eventide Oyster Co are both top oyster spots in town.
Of course, you can’t visit Portland without running into some delicious, fresh caught lobstah. If you’re looking for where to find the best lobster roll in Portland, look to places like the Portland Lobster Co and the Highroller Lobster Co on Exchange St. You can even get a lobster roll flight at Highroller, for cryin out loud!
If it’s classic working waterfront Portland experience you want, you’ll like The Porthole. This seafood restaurant has been in business since the 1920s and prides itself on providing a “true Downeast experience.” This restaurant on the wharf is no fuss, no muss, with aaaaaall the Maine seafood staples!
All in all, Portland is one of those New England towns where there aren’t a whole lot of duds, so you’ll likely end up satisfied at just about any restaurant in the Greater Portland area.
Walk the Portland Freedom Trail
While not as well known as the Boston Freedom Trail, the Portland Freedom Trail offers a similar tour through some of the most significant historical sites of Portland Maine, specifically, its African American history.
Black Mainers played an important role in early anti-slavery movements, and you can find historic sites along the waterfront that were used as a part of the Underground Railroad. This is definitely one of the most historically and socially important of the Portland Maine attractions on this list.
To learn more about Portland Black history, sign up for this highly rated Black history tour that further illuminates the historical significance this port city has played over the years.
Take the Kids to the The Children’s Museum & Theatre of Maine
Are you visiting Portland, Maine with kids? Then this is a definite must visit!
The Children’s Museum & Theatre of Maine offers interactive exhibits that allow your kiddos to experience to flex their creative muscles, as well as to attend professional theatre performances that are perfect for the whole family.
Check out the Children’s Museum events calendar to see what’s onstage during your visit.
Visit the Eastern Promenade
The Eastern Promenade is 68 acres of protected outdoor space on the northeastern slope of Munjoy Hill, where you can walk, bike, or just be while enjoying the lovely Casco Bay and Portland Harbor views.
Want to ride this lovely waterfront trail? Swing by the Portland EnCYCLEpedia to rent a bike. They even offer free biking and walking maps so you can get the insider’s scoop on where to go.
C’mon Ride the Train… at Maine Narrow Gauge Railroad Co & Museum
Not only can you learn about historic trains at the Maine Narrow Gauge Railroad Co. & Museum, but you can hop on one of their trains and take a scenic ride around Portland! Train rides are offered throughout the year, six times a day, seven days a week.
If you’re looking for things to do in Portland Maine in the summer, consider hopping on the Ice Cream Train. Kick back with an ice cream while you chug along Portland’s historic waterfront!
If you’re looking for something a little more adult, consider booking the Sunset Express on Saturday evenings, offering adult beverages (to 21+) and sunset views. This could be a very cool date idea if you’re looking for couples things to do in Portland, Maine.
Refuel at Portland Coffee Shops
Which one, you wonder? Glad you asked! There are so many great coffee shops in this port city because the cozy coffee shop game is strong here. Notable standouts include Coffee Me Up, Speckled Ax, and Tandem Coffee Roasters. All know what they’re doing with the espresso machine, for sure!
Tandem Coffee Roasters on Congress is an especially cool coffee shop to visit while in Portland, because it exists in a repurposed space that was once a gas station, and just gives off that cool updated retro vibe!
Take to the Sea
You’re in coastal Maine, what are you gonna do, not go out on a boat tour? Pssh. Silliness.
There are many different kinds of boat tours in Portland, including an opportunity to take a ride on a traditional, Maine-built windjammer. This highly rated two hour cruise takes place on Maine built wooden windjammers that are listed on the National Register of Historic Places. Wouldn’t this be a unique way to explore the coastal beauty of the area?
If you want to get real fancy, you can opt to book a private charter on a vintage lobster boat. This would be an especially unique event for an anniversary or graduation gift!
Explore Fort Williams Park
Right next to the iconic Portland Head Light, this is definitely a place to visit during your travels. There’s over 90 acres of space to explore, with an Arboretum, walking trails including a cliffside loop, a playground for the kiddos, and more.
While technically located on Cape Elizabeth, there is so much to explore at Fort Williams Park! It’s home to the abandoned Goddard Mansion, built during the Civil War era as a private residence and then later housing a club for non commissioned officers in the army.
Another abandoned place of interest at this park is the Battery Keyes, built in 1906 and last of service during WWII. There is something both eery and intriguing about witnessing places that once held such power and significance being slowly folded back into nature as shrubs and trees overgrow it.
There is also a small, rocky beach called Ship Cove that you can swim at, if you’re interested in braving the chilly Maine waters!
Check Out Urban Farm Fermentory
For a very unique experience, check out the Urban Farm Fermentory. It’s Portland’s one stop shop for fermented beverages like kombucha, gruits, mead, and more. They use local and foraged ingredients in their recipes, too!
They also host a lot of cool events throughout the year, including Sunday Jazz Sessions, Salsa Nights, live music, and other interesting things to do.
Hit the Beach
Whether you’re looking for a place to stroll on the sand or you’d like to take a summer dip in the bracing Maine waters, there are beaches in the Greater Portland area for you!
Willard Beach in South Portland is one of the most popular swimming beaches in Portland area, and it is well equipped for summer swimmers with a bathhouse with restrooms, showers, and a concession stand. You can see Ram Island Light from the beach, too!
East End Beach is the only public beach in Portland proper, and it has restrooms onsite, as well.
If you’re able to drive a little further out, you’ll get to some of the even more scenic Maine beaches like Scarborough Beach, but if you just want to stroll by the sea or take a quick dip, these Portland beaches will do ya just fine.
Where to Stay in Portland, Maine
There are some really cool places to stay in Portland, Maine!
Portland Harbor Hotel is one of the most popular boutique hotels in the city. Perfectly situated for Old Port exploration by foot, Portland Harbor Hotel has an elegant nautical theme that fits this vibrant port city oh so well!
The Press Hotel is one of the more unique local hotels, with decor paying homage to the building’s prior life as the headquarters of the Portland Press Herald.
You’ll find nods to its literary history throughout – keep an eye out for the beautiful vintage typewriters!
Portland, Maine is one of the top places to visit in the Pine Tree State. Any visit to this beautiful coastal city is sure to be a hit whether you’re in the mood for active adventure or something a little slower paced. Happy Travels!
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