Portland: what to see, where to stay and how to get around

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The coast south of Portland is a run of rocky points, each with its light, its old fort or both. The forts guarded the harbour from the 1800s to the Second World War, and most are now parks. This drive starts at the most famous lighthouse in Maine, goes south along the cape, then back up across the bridge to South Portland's two harbour lights. Half a day with stops; finish at Bug Light for the sunset over the city.

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A short history of Portland

Portland, Maine, began in 1633 as an English fishing settlement called Casco, on a peninsula in a bay where the Abenaki people already fished. The settlement was destroyed several times in wars with the Native Americans and the French, and in October 1775, at the start of the War of Independence, a British fleet bombarded it and burned most of it. It received its present name in 1786, and from 1820 to 1832 it was the capital of the new state of Maine. The poet Henry Wadsworth Longfellow was born here in 1807. On 4 July 1866 a fire started by fireworks burned almost the entire city centre, which is why most of the brick buildings in the Old Port were built in the years that followed. Portland Head Light, first lit in 1791, is one of the oldest lighthouses in the United States.

The ten best sights in Portland

1
Casco Bay Lines Terminal
Car-free ferries to the islands leave from here all day; buy a return, the island side has no ticket office
2
Portland Head Light
The park around it is free; come early before the tour buses, or at dusk when they have gone
3
Portland Museum of Art
Strong on Winslow Homer and Maine painters; the museum also runs the tours to Homer's studio by the sea
4
Wadsworth-Longfellow House
The poet's childhood home, with a quiet garden behind it that is free to enter
5
Victoria Mansion
Inside it is far richer than the outside suggests; tours are timed, so book
6
Portland Observatory
Climb the 103 steps for the best view over the city and the bay; open in the warm months only
7
Maine Jewish Museum
Art shows in the 1921 Etz Chaim synagogue, the last of the old immigrant shuls on India Street
8
Old Port
Cobbled streets of shops and bars by the wharves; park once in a garage and walk
9
Eastern Promenade
The hill for sunset picnics over the islands; the small beach below is the only one on the peninsula
10
Fort Williams Park
Ruins of a mansion and old gun batteries around the lighthouse; space to run for those who have been in the car all day

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What is an audio walk?

Tours in Portland →

A guide in your headphones: open the walk on our site, walk from stop to stop, and at each one your phone tells its story. No guide, no group, and free. This is the first walk in Portland:

Free walking tours in Portland

Lighthouses of Cape Elizabeth

Portland Head Light · First lit in January 1791, it is the oldest lighthouse in Maine, built with money from the new federal government under George Washington. The keeper's house is now a small museum.
Goddard Mansion · The stone shell on the lawn is what is left of a house built in the 1850s for Colonel John Goddard. The army later used it as housing for the fort, and today only the walls stand.
Cape Elizabeth Light · This is the lighthouse in Edward Hopper's 1929 painting 'The Lighthouse at Two Lights'. There were once two working towers here, which gave the place its name; only one still shines.
Two Lights State Park · During the Second World War this was a coastal artillery post guarding the approach to Portland. The concrete bunkers are still in the woods above the tide pools.
Spring Point Ledge Light · Built in 1897 on a ledge that had wrecked ships coming into the harbour. For half a century keepers reached it by boat; the granite breakwater you walk on was only added in 1951.
Bug Light Park · The little lighthouse of 1875 is modelled on the Choragic Monument of Lysicrates in Athens, with Corinthian columns around its body. The park around it was a shipyard where Liberty ships were built in the Second World War.

The peninsula on foot

Old Portland sits on a narrow peninsula, so almost everything is in walking distance. Much of the centre burned in the Great Fire of 1866 and was rebuilt in brick and granite, which is why the Old Port looks so Victorian. This walk crosses the peninsula from the hill at its east end to the arts district on Congress Street, about 3 km. Allow half a day with the houses and the museum; most close one day a week, so check before you go.

Portland Observatory · Built in 1807 by Captain Lemuel Moody, the tower used flags to tell merchants which of their ships was coming in, hours before it docked. It is the last maritime signal tower of its kind left in the United States.
Maine Jewish Museum · The building is the Etz Chaim synagogue, built in 1921 by Jewish immigrants from Eastern Europe in the India Street neighbourhood, where most of the city's Jews first lived. Today its galleries show Maine artists, and the old sanctuary is still used.
Old Port · The Great Fire of 4 July 1866, probably started by a firecracker, left about 10,000 people homeless. The brick and granite warehouses you walk past were almost all built in the years right after it.
Victoria Mansion · Built from 1858 to 1860 as a summer house for the hotelier Ruggles Morse, it kept almost all of its original interior, decorated by the New York designer Gustave Herter. It is one of the most complete pre-Civil War houses in the country.
Wadsworth-Longfellow House · General Peleg Wadsworth, the poet's grandfather, built it in 1785-86 as the first all-brick house in Portland. Henry Wadsworth Longfellow grew up here and wrote some of his early poems in it.
Portland Museum of Art · Winslow Homer painted his great sea pictures at Prouts Neck, a few kilometres south. The museum bought his studio there in 2006 and runs small-group tours to it from the museum.

Islands of Casco Bay

Casco Bay is full of islands, some with year-round villages that are still part of the city of Portland. The ferries are the islanders' buses, carrying mail, groceries and children to school. This half day takes the short ferry to Peaks Island, the most lived-in of them, and loops round it by bike, past a Civil War hall, a wartime gun battery and one of the oddest museums in America. Back on the mainland, a kayak trip reaches the fort in the middle of the harbour.

Casco Bay Lines Terminal · The ferries here are the islands' lifeline, and one of the routes still carries the mail round the outer islands every day. Tourists can ride along on that 'mail boat run' for a three-hour tour of the bay.
Peaks Island · About 900 people live on Peaks all year, and it is part of the city of Portland. The road round the island is about 6 km, flat enough for a family on bikes.
Fifth Maine Regiment Museum · Veterans of the Fifth Maine Infantry built this shingled hall in 1888 as a summer reunion house. Inside are their Civil War letters, photographs and flags.
Umbrella Cover Museum · A museum devoted only to the little sleeves umbrellas come in, collected by an island resident, Nancy 3. Hoffman. Its collection holds a Guinness world record.
Battery Steele · Built in 1942 for two 16-inch guns that could fire shells over 40 km out to sea. The guns are gone, and the long concrete tunnel is now covered in graffiti and echoes.
Fort Gorges · Work on the granite fort began in 1858 and ended in 1865, by which time new rifled cannon had already made its walls obsolete. It never saw a shot fired, and today you can only reach it by your own boat or kayak.

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Getting to Portland and getting around

Portland International Jetport · Ten minutes from downtown, with direct flights to New York and other East Coast hubs
Portland Transportation Center · The Downeaster train to Boston and the Concord Coach buses leave from the same building, out of the centre; take a taxi or local bus in

Cheap eats in Portland

Portland eats from the Gulf of Maine: lobster, clams, oysters and haddock, landed on the wharves a few streets from the plate. The lobster roll comes two ways, cold with mayonnaise or warm with butter, and both are worth trying. Prices for lobster have climbed in recent years, so a roll costs more than a full lunch elsewhere, while chowder and fried fish stay cheaper.

Eventide Oyster Co. · Oysters and a brown-butter lobster roll on a steamed bun, about $25-35
The Holy Donut · Doughnuts made with Maine potatoes, about $3-4 each
Duckfat · Belgian fries cooked in duck fat, about $8-12
J's Oyster · Raw bar on the wharf, about $15-30
Gilbert's Chowder House · Chowder in a bread bowl, about $10-20
Highroller Lobster Co. · Lobster rolls and lobster on a stick, about $20-35
Standard Baking Co. · Bread and pastries by the ferry, about $4-9
The Lobster Shack at Two Lights · Fried clams and lobster rolls on the rocks, about $15-35

Museums in Portland

Portland Museum of Art · Winslow Homer and Maine painting
Victoria Mansion · A complete 1860 interior, timed tours
Maine Jewish Museum · Art shows in a 1921 immigrant synagogue
Portland Observatory · 1807 signal tower with a view
Wadsworth-Longfellow House · The poet's family home and garden

Nature and day trips near Portland

Mackworth Island · Easy 2 km path round a small island joined by a causeway
Eastern Promenade · Grassy hill over the bay, East End Beach below
Back Cove Trail · Flat loop round a tidal basin
Crescent Beach State Park · Sandy beach on Cape Elizabeth; the water stays cold
Two Lights State Park · Tide pools and rocky ledges

Things to do in Portland with kids

Children's Museum & Theatre of Maine · Hands-on rooms by the water for younger children
Hadlock Field · Minor-league baseball with the Portland Sea Dogs
Fort Williams Park · Lawns, ruins and a lighthouse to run round
Bug Light Park · Kites and a tiny lighthouse
Peaks Island · Ferry ride and a flat bike loop

Where to eat in Portland

Fore Street · Wood-fired Maine food in an old warehouse; book weeks ahead
Gritty McDuff's · Brewpub in the Old Port
Central Provisions · Small plates in one of the Old Port's oldest buildings
Novare Res Bier Café · Beer garden hidden in an Old Port alley

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Frequently asked questions about Portland

What is there to see in Portland?

The top sights in Portland are Casco Bay Lines Terminal, Portland Head Light and Portland Museum of Art. The full list on this page has 10 sights, each with a photo and a short note.

How many days do you need in Portland?

Three to four days are enough to see the best of Portland without rushing, including at least one walking tour.

Is there a free walking tour in Portland?

Yes. sleepntrip has 3 free audio walks in Portland, with no guide and no group: your phone tells the story at every stop. The first one: Lighthouses of Cape Elizabeth.

How do you get to Portland and get around?

The main ways are Portland International Jetport and Portland Transportation Center. Full details are in the transport section on this page.

Where to stay in Portland, and for how much?

sleepntrip shows only rooms in Portland that meet nine conditions: a good location, high guest scores, cleanliness, and a price of up to $80 a night for two. Pick your dates and see what is free.

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