Coast & harbor city · Maine

Portland Head Light and the Old Port day trip

Portland Head Light and the Old Port

A full day trip from Boston to Portland, Maine. Start with a morning at Portland Head Light, first lit in 1791, and the cliffs of Fort Williams Park. Then park once and walk the rest: lunch in the brick Old Port, the 1807 signal tower on Munjoy Hill, the Eastern Promenade above Casco Bay, an optional ferry ride to Peaks Island and dinner by the wharves.

Time: 13–14 hour day
Driving: About 4½ hours of driving in total, mostly I-95 to and from Boston
Best time: Late May to mid-October
Updated: October 12, 2026 at 7:23 AM Pacific

$4 USD

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Portland Head Light, a white tower beside a keepers' house with a red roof, on a rocky point with waves breaking in a cove below under a gray sky — King of Hearts · CC BY-SA 4.0. October 2021 photograph; resized and displayed with crop.

Suggested times, not bookings

Your day at a glance

7:30 amLeave Boston
9:45 amFort Williams Park and Portland Head Light
11:45 amThe Old Port and the waterfront
1:30 pmPortland Observatory
2:45 pmEastern Promenade and Fort Allen Park
4:30 pmCasco Bay Lines ferry to Peaks Island
6:30 pmDinner in the Old Port and the drive back

Highlights

Worth the trip

Portland Head Light and its keepers' house museum on the Cape Elizabeth cliffs
A guided climb to the top of the 1807 Portland Observatory
Casco Bay views from the Eastern Promenade, or from the Peaks Island ferry

What’s in the guide

Matching HTML and PDF guides, detailed stop guidance, rules, practical pitfalls, a route map, Google Maps, Waze and Apple Maps links, weather alternatives and phone instructions. See an example guide →

Plan for the conditions

Expected seasonal weather

From late May to mid-October, Portland usually has mild to warm days, and it's often cooler and windier on the Cape Elizabeth cliffs and on the water than inland. Fog is common along the coast, especially in late spring and early summer, and can hide the lighthouse for hours before burning off. Summer brings occasional afternoon thunderstorms. By late September and October expect crisp, cool days, chilly evenings and sometimes strong wind and surf after a coastal storm. Late summer and early fall can bring remnants of tropical storms. These are seasonal expectations, not a forecast for your travel date; check the NWS forecast the evening before and the morning of your trip.

Admission and parking are separate. Check current conditions before departure.

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11-hour day·About 2½ hours of driving in total

Best: May to October; best mid-June to early October

$4 USD

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13-hour day·About 6.5–7.5 hours of driving in total, including the Auto Road

Best: Mid-June to early October

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Best: Late May to mid-October; best in June and September

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$4 USD