Portland Maine
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The ULTIMATE Guide to Portland Maine: Things to Do, See, & Experience This Year

Portland Maine offers the quintessential experience of a New England town with a city that’s large enough to scratch the urban itch but small enough to feel like you’re still getting away from the hustle and bustle of a hectic life.

The city boundaries stretch to offshore islands and offer distinct neighborhoods for every interest and appetite. Here you can enjoy lobster, lighthouses, nightlife, and lackadaisical days at sea.

Portland Observatory - Portland, Maine
Portland Observatory | photo via @northernpointphotography

About Portland Maine

There are elements of irony, tragedy, and resiliency that bring us the Portland Maine we know today. Already established as a fishing hub in the 1620s, it was after the Civil War ended that Portland was ready to celebrate its first post-war Independence Day in 1866, complete with fireworks.

It’s believed that one of those afternoon fireworks changed the landscape of Portland. Fires weren’t uncommon in this town of wood buildings, but the worst spot for a spark mixed with shifting winds. It was 16 hours before those winds shifted, leaving one-third of the city in ruins and 10,000 people homeless.

“…the shouts of the firemen, the rattling of engines, the uproar of falling walls and the explosion of mines, the clamor of bells ringing out anew, all overhung with a dark and wired canopy of smoke, lurid with the baleful glare of this great conflagration — all united in creating a night of terror and dismay appalling to the stoutest of hearts.”

Dr. William Wood, head of the Portland Society of Natural History

The first act of rebirth was the building of what is now Lincoln Park, and the rest of the active fishing port and metropolis of Portland began to rise from the ashes, an effort etched into the city’s crest to this day. Had that fire not happened, you’d be visiting a much different city layout.

Portland Maine Weather: What to Expect

Portland gets the epitome of all four seasons, with perfect warm—but not too hot—summer days, crisp fall air backed by stunning foliage, winters so enchanting you can (almost) forget about the bitterly cold temperatures, and spring that brings rebirth and excitement of another summer around the corner.

Sunscreen and bug spray will go a long way in every season but are essential from late spring through early fall. Pack layers of clothing for each season’s temperamental temperature swings, and expect snowfall anytime between November and April.

You’ll want warm, hearty layers of winter clothing and worn-in adventure shoes whether you plan to walk the rocky shoreline, stay afoot on a boat, balance on brick walkways through Old Port, or just walk through the many different neighborhoods.

Stay on track of Hurricane Season from June through November with the National Hurricane Center. Stay updated with CodeRED weather and emergency notifications from Cumberland County Emergency Management.

Casco Bay Lines | photo via thmcjr

Outdoor Things to Do in Portland Maine

Take your left hand and place it in the shape of a “C.” That’s the general outline of the city of Portland, with Back Cove filling the hole in the center. Portland is filled with unique neighborhoods with plenty of outdoor activities.

Trails Around Portland

To get a great lay of the land, check out the 3.6-mile Back Cove Trail that circles the waterway with great views of downtown, Casco Bay, and wildlife. Back Cove Park has a rocky shoreline, playgrounds, and picnic tables.

Or, you could walk the harbor at the Eastern Promenade while exploring the largest Portland Maine park. Don’t miss the view from Fort Allen Park, which inspired poet Henry Wadsworth Longfellow.

Often I think of the beautiful town, That is seated by the sea;

Often in thought go up and down,

The pleasant streets of that dear old town, And my youth comes back to me.

Henry Wadsworth Longfellow, 1807-1882, when describing his childhoods memories

The Harborwalk Trail crosses over the Casco Bay Bridge and spans about 5 miles to the Bug Light Park & Portland Breakwater Lighthouse in South Portland.

PLAN AHEAD: The extensive trail system in Portland Maine is matched with nearby stops on the Southern Maine Transit Tracker.

Boat Tours of the Casco Bay

If those hikes have made you crave the islands in the distance, there’s a boat that goes to all of them! The islands within the Portland city limits include Cliff Island, Cushing Island, Great Diamond Island/Little Diamond Island, House Island, Jewel Island, and Peaks Island.

Tour boats leave from Old Port on the south edge of Portland Maine, and you can get as budget-friendly or luxurious as you choose. Casco Bay Lines is the most dominant ferry service, with options for standard tours, charter trips, lobster bakes, and special events.

For a classic Maine seafaring adventure, don’t miss a chance to ride one of Portland Schooner’s classic windjammers. Or, take your party to the next tide level on a BayCycle Cruise, where the bar is powered by the people celebrating on board.

Fort Gorges | photo via zadley91

Fort Gorges

One of the best “hiding in plain sight” Portland Maine adventures is at Fort Gorges in the bay between the Eastern Promenade and Little Diamond Island.

Boat rides are available to Hog Island, where the fort is located, but be aware that the fort makes up the perimeter and landmass of the island. It is worth the trip to find out why this clever fort was obsolete before even one soldier was stationed here.

Land-Based Tours of the City & Surrounding Area

If you aren’t ready to build up your sea legs yet, take a trip on the Maine Narrow Gauge Railroad. The 3-mile trip takes less than an hour, giving you plenty of time to keep exploring.

Maine Day Ventures helps tourists get the best use of their time while catering to their interests with historic, food, shopping, drinks, and neighborhood tours.

And, you can’t have a city this old without some ghost stories to tell, and the Spirits Alive at the Eastern Cemetery is one of the most popular tour operators to pay respects to those who shaped the city.

Portland's Old Port-Portland
Portland’s Old Port | photo via stephenasheridan

Portland’s Old Port

This section of the city will resonate with you for years to come because of its seaside Victorian palpable spirit and because it was where the Great Fire of 1866 happened, and the buildings as you see them were rebuilt in the aftermath.

Just “being” in the Old Port is an outdoor sensory overload. Take your time walking through the unique stores and restaurants that line the cobblestone streets.

TOO MUCH WALKING? Check out Portland EnCYCLEpedia for a bike rental that fits all members of your family or party.

Lighthouse Lessons

First-timers to Portland are often surprised to find that the Portland Head Lighthouse isn’t in Portland or even South Portland. It’s in Cape Elizabeth Maine and named after the Portland Head peninsula it sits on, not the city. The lighthouse is in Fort Williams Park.

Want to go inside the Portland Head Lighthouse? Plan your trip to match up with Maine Open Lighthouse Day. That’s the only day of the year it’s open to the public.

While the Portland Head Lighthouse is among the most photographed in the world, pay some respect to Ram Island Ledge Lighthouse in the distance. It is not open to the public, but many of those boat tours pass by its location.

Children's Museum & Theatre of Maine-Portland
Children’s Museum & Theatre of Maine | photo via abbyopearson

Indoor Things to Do in Portland Maine

It’s hard to head inside when there are so many outdoor options in Portland, but the secrets of the city and the characters that built this dominant shipping destination are tucked inside historical walls.

Maine Historical Society

The Maine Historical Society is a collection of exhibits and museums showcasing the history and culture of Maine with exhibits that highlight the state’s maritime history, Native American heritage, and early colonial period.

Also on-site is the childhood home of poet Henry Wadsworth Longfellow, which is now a museum showcasing 19th-century domestic life.

Children’s Museum & Theatre of Maine

The interactive Children’s Museum & Theatre of Maine museum is designed for children and families with hands-on exhibits that encourage creativity, exploration, and learning. Don’t let the name fool you, though, because there are After Dark events just for adults throughout the year.

Victoria Mansion

The Victoria Mansion is a National Historic Landmark and provides a stunning example of mid-19th-century architecture and design, showcasing original furnishings and decorative arts. Buy tickets in advance because this popular attraction is often sold out.

Tate House Museum-Portland
Tate House Museum | photo via greatdancindinos

Portland Museum of Art

The Portland Museum of Art boasts more than 18,000 artworks, including American and European paintings, sculptures, and decorative arts. Don’t miss the sculpture park just around the entrance on High Street.

If you’re doing a self-guided tour, ask for cell phone tour information to get the benefits of a guide while moving at your own pace.

Southworth Planetarium

Immerse yourself in the skies above at Southworth Planetarium. This state-of-the-art facility explores the wonders of the universe with rotating exhibits throughout the year on the University of Southern Maine campus. The planetarium has a 30-foot dome and a high-resolution digital projection system.

Tate House Museum

The Tate House Museum is the epitome of an affluent 18th-century home in Portland Maine. It was owned by a noble shipping Englishman named Captain George Tate.

Having survived numerous disasters in the Portland region through the centuries, it is one of the best-preserved colonial homes in Maine, showcasing period furnishings and architecture.

Sebago Lake State Park Naples jb2255
Sebago Lake State Park | photo via jb2255

More Things to Do Near Portland Maine

It’s not that Portland itself doesn’t have enough to see and do, but there are some unique Maine experiences that you don’t want to miss if you’ve made it this far.

Old Orchard Beach

Otherwise known as OOB, Old Orchard Beach is New England’s long-time seaside amusement park town backed by 7 miles of sandy beach.

The boardwalk and pier bring an especially excited crowd from Canada, and it’s yet another town where fire changed the landscape but not the community pride. Palace Playground creates an air of nostalgia and adrenaline with sweeping ocean views.

Kennebunk & Kennebunkport

You don’t have to choose between Portland and the Kennebunks because they are just 30 miles apart. Kennebunk and Kennebunkport bring troves of tourists throughout the summer and a dynamic crowd for the Christmas Prelude.

While you are here, check out the small fishing village of Cape Porpoise for more breathing room but just as much charm.

Sebago Lake State Park

When someone says, “Let’s go to The Lake in Southern Maine,” they’re likely talking about Sebago Lake less than an hour from Portland. You can be landlocked or take the ferry to Frye Island. This is an especially great day trip when coastal winds are kicking up some wicked waves.

The Highroller Lobster Co. Portland Maine @foodwith jae 1
The Highroller Lobster Co. | photo via @foodwith_jae

Restaurants in Portland Maine

Even elite palates among foodies can’t stop raving about the food scene in Portland Maine. Whether you’re waking up early with the lobstering crews or staying out late enjoying the vibe, there is so much more to the Portland food scene than lobster.

Lobsters Hot Spots

Bite Into Maine

When you’re on the go, look for the bright orange Bite Into Maine food trucks or take-out window. You you can order in person or ahead of time, and don’t forget the classic New England whoopie pie for dessert.

Becky’s Diner

Becky’s Diner on Hobson’s Wharf can make lobster part of your breakfast, lunch, or dinner while keeping it casual and laid back. The food even made headlines on “Diners, Drive-Ins and Dives” with Guy Feiri. You walk in a stranger and leave as part of the family because of this home-cooked haven in Old Port.

Highroller Lobster

Highroller Lobster started as a low-budget hot dog cart and is now one of the top stops for some creative lobster and cold brews. You’ll love the food as much as the funky vibe that this close-knit team offers. Ask how the Lobster Cheese Crisp Taco became an accidental sensation.

Hot Suppa-Portland
Hot Suppa | photo via wakemewhentheresfood

Casual Dining in Portland


Using #sausagebythesea, the THiRSTY PIG team mixes meats with many beer options, giving you the perfect blend of casual seating while still ordering at the counter. No reservations, no VIP, and no more than 50 guests at a time make this a place where you’ll miss out if you don’t at least try to snag a spot.


In a town of slick names, Duckfat tells the full story in one word. Known worldwide for its Belgian fries cooked in duck fat to crispy perfection, one location wasn’t enough.

Look for the Duckfat Frites Shack if you want to grab-and-go. You can also choose a healthy(ish) duck-fat-fried Brussels sprouts or one of the other items that turn fries into the main dish, and everything else is a side dish.

Hot Suppa

Bringing Southern cooking to New England, Hot Suppa serves the brunch crowd with soul food and Mardi Gras-inspired drinks. Creole quiche and the Mother Clucker make ordering a fun event itself. The made-from-scratch meals have quite a cult following, so don’t be surprised if there’s a wait.

ViA VECCHiA Portland Maine @shelbysfood 3
ViA VECCHiA | photo via @shelbysfood

Elegant & Upscale Dining


Look for the ivy-covered bricks to find the small-plate inspiration of ViA VECCHiA. Velvet booths and sophisticated bartenders impress, but it’s the bathroom that really gets raves for its welcoming design with no detail overlooked. Make reservations, and drink enough that you have to answer the call of nature.

David’s Restaurant

David Turin has made a name for himself across Maine, and it all started at this intimate David’s Restaurant location on Monument Square. Look to David’s Opus Ten for elevated dining experiences with revolving tasting menus throughout the year.

The ambiance is welcoming, but the dedication of Chef David and his willingness to engage with the community are what really stand out.

Harbor Bistro & Terrace

The ingenious Harbor Bistro & Terrance is missing nothing but a lunch menu, as the breakfast and dinner options offer indoor and outdoor seating near an open pit fire or a warm stone fireplace.

Dinner guests can choose from secluded Fire & Ice Igloos for an additional fee, making this one of the unique experiences in a town where uniqueness is hard to achieve.

Ugly Duckling Bakeshop & Luncheonette-Portland

Coffee Shops & Bakeries

Ugly Duckling Bakeshop & Luncheonette

One of the newest jolts to the dining scene is the Ugly Duckling Bakeshop & Luncheonette with famous Trocadero treats and an expansive list of coffee and espresso. The menu looks simple, but then you’ll notice the red-eye espresso and realize short and sweet can still surprise you.

Holy Donut

Dear Lord, you’ll need to get in line early to try out The Holy Donut. Ponder the fact that some doughnuts are made from potatoes or rice while finding patience in knowing how this bakery gives the leftovers to local organizations.

The menu listings are far from the traditional doughnut shop names, with a Holy Cannoli Ginger Glazed and Sweet Potato Coffee Cake being some of the most ordered.

Beals Famous Old Fashioned Ice Cream

Ice cream is its own food group in New England, and Beals Famous Old Fashioned Ice Cream has two locations to satisfy your sweet tooth. Sure, get a cone or a sundae, but how about an ice cream pie or full-sized ice cream pizza? Dairy-free and sugar-free options are available too.

Urban Farm Fermentory-Portland
Urban Farm Fermentory | photo via paige.jimmy

Brewery Tasting Rooms

You can’t put 12 ounces of beer in a shot glass, and that’s what it feels like when you’re trying to whittle down the Portland Maine brewery options. But, here are a few that you don’t want to miss.


The name is Hi-Fidelity, but the signature is low alcohol per volume of beer in the trendy setting of the East Bayside neighborhood. All beer is under 6% APV, with malt sodas made from the wort that also crafts the beer.

Entertainment, like live bands and open mic nights, gives you something more to cheers to throughout the week.

Urban Farm Fermentory

Urban Farm Fermentory goes beyond brews, expanding into cidah, kombucha, vinegar, mead, and Jun tea. The Portland tasting room offers a mixed vibe of industrial and rustic with a splash of nature. Events include live music, film festivals, and eco-friendly discussions.

Portland Harbor Hotel-Portland
Portland Harbor Hotel | photo via themoodybluebird

Hotels in Portland Maine & Other Lodging

The Francis

Reserve some space in the West End neighborhood of Parkside at The Francis. With just 15 rooms and centuries of Maine experience between all the owners, you’ll get an archetypal experience just a short distance from the hustle of downtown and Old Port.

An on-site spa and luxury amenities also give you a great reason for a night in.

Inn at St. John

Just 31 years after the Great Fire of 1866, this inn was built, and what is now called the Inn at St. John is still standing today, waiting for guests as an independently owned and operated historic accommodation.

The inn has rooms for the budget class to luxury lovers, and it ditches any cookie-cutter room layouts. Free breakfast comes with all overnight stays.

Portland Harbor Hotel

The Portland Harbor Hotel brings a nautical theme with classic New England charm into one perfect location for exploring Old Port and downtown Portland. From standard rooms to executive suites, you’ll enjoy wood floors, local artwork, and down pillows.

Inn at Diamond Cove

When you really want to get away in Portland Maine, stay on an island at the Inn at Diamond Cove. This luxury, offshore stop includes condominiums with all the amenities that a distinguished traveler could want.

There are several restaurants on the property, so you can avoid going back and forth on the ferry to dine. You’ll also have a car-free island to explore with beaches, forests, and marshes waiting.

Longfellow Hotel

Longfellow Hotel is an independently-owned option that includes a Nordic spa and 48 rooms throughout five stories. This boutique hotel offers a fresh perspective on luxurious and refined, yet subtle and reserved, accommodations that complement the natural and historic splendor of Portland.

EDITOR’S NOTE:  Longfellow Hotel is scheduled to open for the summer 2023 season, and Vogue ranks it as one of the most anticipated hotels in the country.

Holy Donut-Portland
Holy Donut | photo via ctcoffeeandcarbs

A Trip to Portland Maine Worth Is It

Portland Maine is well aware of where it has been and where it is going while somehow managing to overachieve on all accounts.

The growing and evolving restaurant scene means that you’ll never have the same experience twice, but the high expectations and idyllic seaside views make it seem so comfortably familiar at the same time.

Don’t wait too long to decide. This city is on hot travel lists even in the dead of winter, and reservations fill up quickly.

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