Portland is a small working port on Casco Bay that happens to have one of the best restaurant scenes in the United States. The Old Port's cobbled streets and brick warehouses sit directly above a harbour that still lands fish, and the city is compact enough to walk end to end. On a foliage road trip it is the pivot: the point where you come down out of the White Mountains, the colour changes from maple to oak and salt marsh, and you eat properly for the first time in a week.
- One of the great food cities in America, at a fraction of Boston or New York prices
- A genuinely walkable harbour city — the Old Port is cobbles, brick and working boats
- Coastal Maine turns two to three weeks after the mountains, so the colour is still ahead of you
- Lighthouses, islands and the Casco Bay mailboat within twenty minutes of downtown
- The natural break between the White Mountains and the long drive up to Acadia
Region: Northeast Best time: Mid to late October for colour — southern and coastal Maine is the last part of New England to turn, peaking around 21–27 October by the state's own reckoning. Summer is busy and lovely; the food is good all year. Getting there: Two hours north of Boston on I-95, two hours east of North Conway, three hours south of Bar Harbor. Portland International Jetport (PWM) has US connections but no direct UK flights — most UK visitors arrive via Boston. Getting around: Downtown and the Old Port are walkable and parking is easier than Boston. You need the car for the lighthouses and to carry on up the coast.
Neighbourhoods
Old Port
Cobbled streets, brick warehouses and most of the restaurants, right above the working waterfront.
East End & Munjoy Hill
The residential hill above the harbour, with the Eastern Promenade walk and the best views in the city.
West End
Victorian and Federal houses, quieter streets, and the Western Promenade looking inland.
Arts District
Congress Street — the Portland Museum of Art, galleries and the older theatres.
Cape Elizabeth
Fifteen minutes south for Portland Head Light and the cliff walk at Fort Williams.
Things to do
- Eat — This is the reason people come. Book the good places before you fly; the best of them take reservations a month out
- Portland Head Light — The most photographed lighthouse in America, at Fort Williams Park in Cape Elizabeth
- The Eastern Promenade — A clifftop path around Munjoy Hill with the whole bay laid out below
- Casco Bay mailboat — Three hours riding the working mail run out to the islands and back, for the price of a ferry ticket
- Portland Museum of Art — Homer, Wyeth and a strong American collection, plus Winslow Homer's studio by tour
- Route 1 north — The alternative to the interstate — Freeport, Camden and Rockland on the way to Acadia, and worth the extra hour
A few perfect days
- Day 1Arrive and eat
Come down from the mountains in the afternoon, walk the Old Port, and have the best meal of the trip.
- Day 2Lighthouse and islands
Portland Head Light in the morning light, then the Eastern Promenade or the mailboat run out into Casco Bay.
- Day 3Up the coast
Take Route 1 rather than I-95 — Camden and Rockland break the drive and the coast is the point.
Eat & drink
- Lobster rolls: cold with mayonnaise or warm with butter, and everyone has a firm opinion
- Oysters from the Damariscotta River, some of the best cold-water oysters anywhere
- A serious independent restaurant scene, plus superb bakeries — queue for the morning buns and do not resent it
- Allagash and the Maine brewery scene, much of it walkable from downtown
Road trips through Portland
National parks & day trips
Where to stay
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