A working harbour, an island ferry, and a headland with two lights
Portland, Maine · 2 nights · June–October · up to 8
Portland is a small city that eats like a large one, and the Old Port is walkable end to end in twenty minutes. The mail boat runs out into Casco Bay several times a day and costs almost nothing — take it once for the whole loop and once to get off at Peaks. Two nights is the honest number; the third day is a drive up the coast, which is a different trip. Book dinner before you book the room.
The ending
A headland of dark ledge rock south of the city with two light towers standing behind it, swell coming in against the shelves, and open Atlantic and nothing else in front of you.
That is Two Lights State Park headland. See how private it is and when it’s open.
Do
- Casco Bay Sunset Cruise
- Peaks Island Day Trip
- Portland Food Tour
- Pottery Class at Portland Pottery
Eat
- Eventide Oyster Co.
- Fore Street
Stay
- The Press Hotel
- The Francis
Why not Portland Head Light?
Because it is the photograph everyone already has, and the park it stands in clears out at closing. Two Lights is a few minutes further along the same headland and it is rock and ocean rather than a queue.
Is two nights really enough?
For the city, yes. Everything north of here — Camden, Acadia — is a separate trip, and pretending otherwise makes both of them worse.
The planner doesn’t build Portland, Maine yet — we can name the places here but not yet enough of them around it to fill 2 nights without repeating. Read this one, then build your own somewhere we can.