25+ Fun Things to Do in Portland, Maine

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If you’re looking for a fantastic and underrated city in the US, I will sing you the praises of Portland, Maine! This incredibly cool city is one of my favorite places in New England — yet it doesn’t get a fraction of the attention it deserves.

Why is that? I think it’s because so many people default to Portland, Oregon, in their minds. That and most Maine visitors seem set on beaches and the outdoors rather than a city getaway. But there are SO many great things to do in Portland, Maine — and I think this city might be the highlight of your Maine trip.

As a native New Englander, I’ve visited Portland many times, but I’ve been visiting more frequently since my close friends moved there a few years ago. Because of that, I’ve been able to explore Portland both through a tourist’s eyes and through a local’s eyes.

While it’s the largest city in Maine, Portland still has a small-town feel with a population of just under 70,000 people. There is so much rich history, everywhere you look, and it’s beautifully set on Casco Bay, overlooking dozens of islands.

But Portland has become increasingly known as a foodie city for those in the know. If you’re looking for cutting edge cuisine, this is a great spot to splurge — but if you’d rather keep it basic, the lobster rolls and donuts here are second to none.

And this might be anecdotal, but Portland is home to some of the nicest, friendliest, most welcoming people I have met, anywhere. (Honestly, I think it’s tied with Asheville for the nicest people in the US!) I’ve had so many great conversations with Portlanders, from ferry passengers to baristas and brewers.

So how should you spend your time in this delightful city? Let’s take a look at the best things to do in Portland, Maine!

This post was published in June 2025 and was co-written by Adventurous Kate and Dale Peterson.

Red brick lanes in Portland Maine with lots of cool shops.

Best Things to Do in Portland, Maine

Walk along the waterfront and Old Port

Start your visit to Portland with a stroll through the Old Port. This historic waterfront district is full of cobblestone streets and stately brick buildings. Commercial Street, which runs right along the waterfront, is the vibrant main thoroughfare here.

On Commercial Street, you’ll find plenty of shops, restaurants, and bars, many of them set in Portland’s trademark red brick style. During the warmer months, there’s usually live music too.

There are lots of great independent shops and boutiques in this area worth visiting. Pinecone & Chickadee is full of cute, quirky gifts that your loved ones will get a kick out of. Viand Mercantile has lovely upscale homewares. And I got my cats some fun mouse toys at Uncommon Paws, a lovely little pet store.

Go on a Portland Maine food tour

Portland is such a good food city, and a food tour is the perfect way to dive in and explore! I always love doing a food tour on my first day in a new city, because it introduces you to the local specialties and shares a few favorite spots with you.

Keep in mind that many Portland tours focus heavily on seafood, so be sure to double-check if you’re not a seafood fan.

The Old Port Culinary Walking Tour combines a historic walking tour with tastings at between five and seven local eateries, with enough food to count as a meal.

The Seafood Lovers Lunch Walking Tour combines a historic walking tour with some seafood tastings, including a cup of chowder and a lobster roll.

And if you want something street, check out the Portland Maine donut tour! Portland punches way above its weight when it comes to donuts (more on that below). This tour showcases three of the best donut shops and has six tastings.

A huge white lighthouse perched on the rocky edge of the sea, topped with light fog.

Visit all the lighthouses

Lighthouses are an iconic symbol of Maine — on par with the lobster roll! With more than 65 lighthouses along the coast throughout the state, you can find half a dozen within 20 minutes of downtown Portland.

The most famous lighthouse near Portland is the Portland Head Light. This is the oldest operating lighthouse in Maine, and it’s been standing since 1791 (although renovated many times over the years).

This lighthouse is a 15-minute drive from downtown Portland, set amongst the spectacular homes in Cape Elizabeth, and it’s the most photographed lighthouse in the US. There is a really nice cliff walk that you can enjoy, photographing the lighthouse from different directions.

Just be warned — you might get a strange fog, like I did on my most recent visit!

Other nearby lighthouses within a short drive of Portland include Portland Breakwater Light in Bug Light Park; Spring Point Ledge Lighthouse; Ram Island Ledge Light Station (this one is way off the coast but you can see it well with binoculars or the zoom lens on your phone or camera); and the two lighthouses at Two Lights State Park.

If you only visit one lighthouse, I’d make it the Portland Head Light, because of how picturesque it is. It’s also the only lighthouse with a museum that’s open to visitors.

A huge windjammer boat with big sails in Portland's harbor.

Go on a windjammer cruise

If you’re visiting Portland when the weather is nice, getting out on the water is a must. Sure, you could take one of the many ferries — but why not hop on an authentic windjammer cruise, huge sails hoisted in the air?

There are few images more quintessential to New England than a windjammer sailing through the islands of Casco Bay!

This two-hour afternoon cruise is the perfect way to take in the sights of Casco Bay from a sailboat, enjoying views of the coastline, lighthouses, and if you’re lucky, maybe even some wildlife like seals. The cruise is BYOB and food, so be sure to pack some drinks and snacks for the trip.

Another option is a two-hour sunset cruise, which offers the same experience with the added ambiance of golden hour and sunset. Be sure to bring a warm layer, because Portland gets chilly as soon as the sun goes down, even in peak summer.

Four people on the bow of a ferry off the coast of Maine, looking at islands.

Sightsee from the water

Another great water experience in Portland is a sightseeing cruise. These cruises offer live narration of all the sights you’re passing, including historic lighthouses, forts, and ports. You’ll get incredible photos throughout your journey.

These cruises tend to be a bit steadier than the windjammers, so I recommend them if you’re a bit nervous about seasickness.

This sightseeing cruise is highly-rated, or you can choose to do it at sunset instead. Note that sightseeing cruises and other boat tours only operate from early May through late October.

Old-fashioned wooden buildings in a row in Portland, Maine

Take a land-based sightseeing tour

Joining a sightseeing tour on land is also an excellent way to gain a deeper understanding of Portland, its history, and its culture. Tours like this are also a good option if you don’t have a car with you on your trip to Portland!

One of the best tours is The Real Portland Tour, which includes a local guide and a tour of the city, as well as stops at three nearby lighthouses. Here’s a similar tour that is also highly rated.

If you’d prefer a more active adventure, one of the best things to do in Portland Maine is this cycling tour that includes visits to five lighthouses and includes a lobster roll lunch.

Or for something unique, check out this vintage fire truck city tour of Portland.

A bird's eye view of Portland, Maine, with rows of suburban streets with triple-decker houses, leading up to a coastline.

Join a walking tour

Walking tours are one of my favorite ways to explore a new city. It’s a great way to familiarize yourself with your surroundings and find the best spots you want to return to later.

One of the top walking tours in Portland is the Hidden Histories tour. Perfect for history buffs, this small-group tour takes you on a deep dive into over 400 years of Portland history with a knowledgeable local guide.

A senior woman standing in front of a display of umbrella covers, some of them forming the word "welcome."

Visit Peaks Island (and the Umbrella Cover Museum!)

Peaks Island is one of the Casco Bay Islands, and it’s the perfect place to spend the morning or afternoon on one of your days in Portland. This is one of my favorite places to visit in Portland, Maine.

Peaks Island has a quaint small-town feel with around 1,000 year-round residents, and a handful of shops and seafood restaurants. The best way to see the island is to rent a bicycle or golf cart and explore on your own. You can also kayak and beach-hop here.

But my absolute favorite thing to do in Peaks Island (hell, it’s my favorite thing to do in Portland, Maine!) is to visit the Umbrella Cover Museum. No, not an umbrella museum — this museum is specifically dedicated to the sleeves that cover umbrellas!

This museum is run by the lovely Nancy 3. Hoffman, and she will make sure you laugh, smile, and sing along with her song about umbrella covers. She even has a room full of SEXY umbrella covers!

I had the biggest smile on my face the entire time I was here.

The Umbrella Cover Museum is open from Memorial Day through Labor Day.

Peaks Island is only accessible by ferry from Portland. The journey takes approximately 20 minutes and tickets are $14 round-trip from mid-April through mid-October. During the off-season, you can get tickets for 50% off.

A big stone fort on an island in the middle of the harbor off the coast of Maine.

Visit Fort Scammel

Fort Scammel is a unique piece of history located on a small private island in Casco Bay. Constructed in 1808 to defend the Portland coastline during the War of 1812 against the British, Fort Scammel has a long and interesting past.

Today, the fort and the island it’s on are privately owned, so the only way to visit is on a tour operated by SeaPortland. However, the tour is definitely worth it, especially if you’re a military history fan or you just want to get off the beaten path.

You’ll take a boat ride to Fort Scammel, then spend time learning about its history and exploring the ruins of the fort and its catacomb-like network of underground passages.

A big dish of Asian-style tofu and noodles.

Dine out at Portland’s best restaurants

Portland is a culinary gem of a city — one that has an incredible number of outstanding eateries for a city of its size. On my many trips to Portland I’ve had the pleasure at eating at quite a few of them.

Here are some of my favorites:

The High Roller Lobster Co — A great place for lobster dishes near the Old Port that feels, fun, celebratory, and cool. The beer and cocktail list are nice, too. The outdoor courtyard has a great mural and a 12-foot skeleton from Home Depot.

The Honey Paw — This restaurant specializes in Asian fusion dishes and is right by the Casco Bay ferry port, which makes it a great post-island hop spot. Everything on the menu is dynamite, but you must end with the honey soft serve with chocolate shell and honeycomb!

Pai Men Miyake — This Japanese restaurant not too far from the Old Port is an evergreen favorite amongst both locals and visitors. While there are so many good dishes on the menu, go for the spicy scallop roll with kewpie mayonnaise, togarashi, and avocado.

Duckfat — Duckfat is a Portland legend with three locations nowadays. They make really tasty sandwiches, salads, and small plates, served with incredible Belgian-style fries cooked in duck fat. (So know that the fries aren’t vegetarian here.) If you want to skip the long line, order some sandwiches to go from the Washington St. location!

Ramona’s Sandwiches — This little shop in the East Bay neighborhood turns out some truly off-the-wall sandwiches. I loved my Italian sub (and easily could have split it with another person) — they also have a roasted pork sandwich with broccoli rabe, a market street vegetable-heavy sandwich, and a breakfast hoagie, among others.

Norimoto Bakery — This little bakery is off the beaten path in the suburban Deering Center neighborhood, but they are a James Beard Award-winner (I happened to be there the morning after they won!), specializing in European-style pastries with Japanese flavors like black sesame, yuzu, miso, and red bean.

Woodford F&B — Another off the beaten path spot in the Back Cove neighborhood, Woodfoord F&B has the feeling of an upscale retro diner and specializes in hyper-local fare — incredibly fresh seafood seafood and produce, as well as steaks, burgers, and Maine specialties. I love their salmon.

This is just a small taste of what Portland has to offer. I recommend you do your research as well and see what sounds good to you!

Kate taking a selfie in front of a giant Bigfoot statue with other cryptids around his feet.

Check out the museums

Portland is home to some great museums in case you need a rainy day activity or just want to check out a cool exhibit. One of the best museums to visit is the Portland Museum of Art, which houses a nice collection of American and European masterpieces.

If you’re looking for something on the strange and quirky side, pay a visit to the International Cryptozoology Museum, which is dedicated to mysterious creatures like Bigfoot, the Loch Ness Monster, mermaids, and more. I found this place hilarious and took photos of everything!

For families with young children, the Children’s Museum & Theatre of Maine is a good option, featuring interactive and educational exhibitions for kids. My friends with kids are members and visit often!

A few bright red Japanese maple trees on a hillside park next to the ocean.

Walk Along the Eastern Promenade

The Eastern Promenade — or Eastern Prom, as locals say — is a lovely promenade and park along the East Bay of the city.

This beautiful waterfront park starts at the corner of Commercial Street and Franklin Street. There’s a 2-mile paved walking trail right along the waterfront with stunning views of Casco Bay, as well as several parks and green spaces as you follow the trail.

If you’re looking for a beach within the city, East End Beach is also here. It’s not much of a beach for taking a dip, but it’s a popular spot to hang out on a sunny day, and pleasant place for a walk year-round. You can rent kayaks and dinghy boats here.

Two men sitting in camping chairs in the middle of a park as fog swirls around them.

Visit Fort Williams Park

Fort Williams Park is about a 20-minute drive from Portland on Cape Elizabeth. It’s where you’ll find the picturesque Portland Head Light lighthouse, but there are a number of other historic sites to explore.

Some other highlights of this park include the ruins of Battery Keyes and the Goddard Mansion. The park also has walking paths and incredible waterfront views. You can find a small collection of food trucks here during the warmer months — yes, including lobster roll trucks!

And on the drive to Cape Elizabeth, be sure to enjoy gawking at the huge, glorious houses. People have some REALLY nice summer homes up here.

Kayak in the bay or on a lake

One of the best outdoor activities to try in Portland during the summer is kayaking. Kayaking in Casco Bay is a popular pastime for Portlanders. If you’re looking for a more placid environment, you can kayak in Sebago Lake, the second-largest lake in Maine, which is about an hour’s drive from Portland.

This is a great kayaking tour in Casco Bay. You can also book a sunset kayaking tour for a beautiful experience in the bay.

If you prefer kayaking on your own without a guide, you can rent a kayak right in Portland at East Bay beach, or get a half-day kayak rental at Sebago Lake.

A box filled with six tiny donuts in different flavors, some covered with sprinkles or frosting.

Go on a donut crawl!

You might think Portland’s main foodie highlight is its seafood, but don’t forget about its donuts! I’m serious — Portland has an amazing donut scene, and I made it my mission to try as many as possible.

The Holy Donut is the most famous donut spot in Portland, and they specialize in potato donuts. The location in the Old Port district often has lines out the door, so arrive early, or opt for their location on Park Ave., far from the tourist crowds.

Another must-visit donut shop near the Old Port is Eighty-8 Donuts, which serves packs of six little donuts in their own container. Super cute, and super Instagrammable!

A donut shop you won’t find without help from a local is Tony’s Donut Shop, an old school donut shop in a more suburban part of the city. This is where you go for a classic donut — I loved my old-fashioned.

Would you like to sample donuts on a tour? Check out the Portland Maine donut tour, which visits three shops and includes six tastings!

Four tasting glasses of kombucha labeled "Root Wild" on a wooden board.

Go beer tasting, spirit tasting, and more

In addition to its outstanding restaurant scene, Portland is known for creating some absolutely delicious beers, kombuchas, and spirits. You could spend a whole day stopping at different places (I know I did!).

You can go brewery-hopping yourself, or take a fun tour like the Portland Beer Bus Tour or a walking tour of some of Portland’s best pubs and breweries.

Some breweries I’ve enjoyed are concentrated around the Washington Ave. area, like Orange Bike Brewing Co, Belleflower Brewing Company, and Hi-Fidelity. But honestly, there are dozens of breweries in and around Portland. Dive on in!

If you enjoy craft distilling and spirits, Maine Craft Distilling is a must. They always have a fun collection of spirits on their menu for sampling, like Blueshine Blueberry Liquor and Queequeg Spiced Rum, along with cocktails and some light eats.

Not into beer, or booze? You can also go kombucha tasting at Root Wild Kombucha in Portland. (Know that kombucha contains trace amounts of alcohol.)

Please remember not to drink and drive. Portland has Uber! Use it!

A skyline view of Portland, with minimal skyscrapers but lots of trees and brick buildings.

Enjoy the view from the Portland Observatory

Located in downtown Portland, the Portland Observatory offers some of the best views over the city. Although it resembles a lighthouse, it’s actually a historic maritime signal tower built in 1807.

If you’re up to the challenge of climbing seven steep flights of stairs, you can take in panoramic views of Portland from above. This is easily my favorite view in the city — I love looking east to Casco Bay and the islands, as well as the city skyline to the southwest!

The Portland Observatory is only open from Memorial Day through Columbus Day, and tickets are $10 for adults. Both guided tours and self-guided tours are available.

An old brick mansion in Portland, Maine.

Visit the historic homes

Portland has some beautiful historic homes that you can visit, showcasing a wide variety of architectural styles. The Victoria Mansion, a National Historic Landmark, is a beautifully preserved Italianate mansion constructed in 1860.

You can also tour the Wadsworth-Longfellow House, which was home to the poet Henry Wadsworth-Longfellow’s grandparents. This impressive Neoclassical home dates back to 1786.

Another historic home in Portland you can visit is the Tate House Museum. Dating back to 1755, it’s among the oldest surviving homes in Portland. Originally built for a British Royal Navy captain named George Tate, this home offers a glimpse into life in colonial Portland.

A few men, one shirtless, working out on a boat surrounded by oyster cages in the still water.

Tour an oyster farm

If you’re looking for a unique experience near Portland, why not tour a working oyster farm? This hands-on experience at a family-owned oyster farm in Phippsburg (about one hour from Portland) allows you to learn all about the oyster production process.

You’ll hop on a boat to visit the oyster farm, where you’ll have the chance to shuck oysters yourself and later on enjoy eating some fresh oysters.

A minor-league baseball game in a small but packed stadium.

Catch a Portland Sea Dogs Game

Maine doesn’t have any major league sports teams, and most people from Maine are fans of Boston’s sports teams. However, Portland does have its own minor league baseball team, the Portland Sea Dogs, which is a Double-A affiliate team of the Boston Red Sox.

Minor league games are super fun, for kids as well as adults; the players have a great attitude; and a lot of fun is infused into these games.

If you’re in Portland during baseball season (April through September), you might be able to see a home game at Hadlock Field. You can check the upcoming game schedule on the Portland Sea Dogs website.

With tickets starting at $15 to $20, it’s a lot more affordable than most major league sporting events, but still a lot of fun.

A big Victorian house underneath orange fall leaves in Maine.

Take a Day Trip in Maine or New Hampshire

There are so many wonderful towns along the southern coast of Maine — you could visit a different town each day for a week and still have more to explore. Here are some of my top recommendations:

Freeport, Maine. Freeport is about a 20-minute drive north of Portland and is world-famous for being home to the LL Bean Outlet! This giant store is an experience, sells virtually any piece of outdoor gear you can imagine, and you have to take a photo with the giant boot out front.

Boothbay Harbor, Maine. Boothbay Harbor is a small coastal town about an hour and 20 minutes north of Portland. While the town is tiny and pretty, the Coastal Maine Botanical Gardens are extraordinary and well worth a visit.

Kennebunkport, Maine. Kennebunkport is about a 35-minute drive south of Portland and is one of the most picturesque spots in southern Maine. This town might be most famous for being home to the Bush family compound, but don’t miss the excellent restaurants and quiet beaches nearby.

Ogunquit, Maine. Ogunquit is about a 45-minute drive south of Portland and is home to gorgeous beaches, lots of art galleries, a wonderful theater, and a vibrant LGBTQ community. Ogunquit is probably my favorite Maine town for photography opportunities. You can read more about Ogunquit in my Ogunquit guide.

Kittery, Maine, and Portsmouth, NH. I am a huge fan of Portsmouth, New Hampshire, a quirky seaside city about an hour’s drive south of Portland, and visit often. This is a great town for brewery-hopping, shopping, and taking in the many historic sites.

Just across the bridge is the town of Kittery in Maine, which is home to excellent outlet shopping and some pretty beaches. The two towns pair well as a single day trip together. You can read more about Portsmouth in my Portsmouth guide on New Hampshire Way and more about Kittery on my Kittery guide.

Just one quick note — Acadia National Park is too far for a day trip from Portland. The drive is about two hours and 45 minutes. Save Acadia for its own trip — it’s a special place!

A narrow building between two streets in Portland, Maine.

Where to Stay in Portland, Maine

Where should you stay in Portland? The best place to base yourself in Portland is the Old Port or Downtown. You’ll be able to get around on foot fairly easily, and supplement with Uber or a bit of driving when you need to. All of the hotels below are in one of these two areas and close to the waterfront.

These are some of the best places to stay in Portland for every budget:

Top-Rated Luxury Hotel in Portland: The Press Hotel is one of the best places to stay in Portland. This boutique luxury hotel is centrally located in the heart of the city and occupies the former Portland Press Herald newspaper offices.
Top-Rated Mid-Range Hotel in Portland: Another great option for where to stay in Portland is Canopy By Hilton Portland Waterfront, a modern mid-range hotel. Portland Regency Hotel & Spa is another good mid-range hotel.
Top-Rated Budget Hotel in Portland: If you’re looking for a budget-friendly option, Courtyard by Marriott Portland Downtown/Waterfront is a great choice.

Find deals on places to stay in Portland here.

A view of Portland city across the water, with a small rope fence in front of greenery in the foreground. Boats are sailing in the water.

Best Time to Visit Portland, Maine

When should you visit Portland? If you’re coming to visit Maine, there’s a good chance you’re coming in the summer or fall, and those are the two most beautiful and most popular times of year to visit Portland!

June through August is a great time to visit Portland if you want to enjoy warm summer weather. With temperatures in the high seventies and sunny, the summer months in Portland are absolutely stunning. This is also the most popular time to visit Portland, giving the city a lively atmosphere with plenty of outdoor events and festivals happening.

Fall is another excellent time to visit Portland, especially September and October. The weather cools off in the fall, but it’s still pleasant, and you can enjoy the colors of the changing leaves, which should be around their peak in early October.

You can visit Portland in winter and spring, but prepare for colder temperatures, fewer opening hours, and a quieter city. Winter in Portland doesn’t get that bad given its coastal location, but snow is common and temperatures often fall below freezing.

That said, winter is a great time to have a truly local experience in Maine. You’re not a true Mainer unless you’re here in the winter months!

Spring is also chilly, and “mud season” in northern New England. If you’d like a pleasant and warm spring trip, I’d recommend visiting in May or June. It still feels like winter to most non-locals as late as April!

A small pink cottage with a golf cart parked in front of it.

How to Get to Portland, Maine

What are your options for getting to Portland? As the largest city in Maine, Portland is also home to the state’s major airport, Portland International Jetport. There are nonstop flights to Portland from more than 15 cities in the United States, mainly cities on the East Coast and some cities in the Midwest.

If you’re already in the Northeast, you can easily take the train or drive to Portland. From Boston, it’s just 2.5 hours on the train and under two hours driving to get to Portland. And from New York, you can take a New England road trip and get to Portland in 5.5 hours driving.

When it comes to getting around, your best bet is to have a car. Portland does have a public transportation system, but it’s limited. Having your own car will make it a lot easier to get around, especially if you want to visit lighthouses or take other day trips.

That said, I found it easy to get around Portland with a combination of driving and using Uber in between so I didn’t have to keep finding and paying for parking everywhere.

A street with boutiques on it in Portland, Maine, old-fashioned gas lamps on the street.

How Much Time To Spend in Portland, Maine

How much time do you need in Portland? Portland is a fairly small city where you can pack a lot into just a few days, making it a great destination for a long weekend getaway. Two days should give you a good amount of time to see the basics.

Three full days is a better amount of time to experience all the city has to offer, take a boat trip, see a few lighthouses, and take a day trip to a nearby destination like Kennebunkport or Freeport.

And if you want to come for longer, that’s great! I would love to spent a week or so in Portland in the future and dive into the city even more than I already have!

Kate taking a smiling selfie in sunglasses in front of a fog-surrounded lighthouse in Maine.

Is Portland, Maine Worth It?

I think Portland is one of the most underrated cities in the US! I really enjoy spending time here, and I know I’ll continue to visit — not only to visit my friends, but because I love the city that much.

I hope you take the time to give Portland the attention it deserves — even if you’re just here for a day or two before heading further up the coast to Acadia.

I hope you have the best time in Portland, Maine! Then get back and tell me all about it.

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Have you been to Portland? Any suggestions? Share away!

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