Dates are flexible. This day-by-day plan is provisional until you choose exact travel dates.
Leave Portland around 10:30 AM and follow US-1 north toward Rockland, allowing roughly 1 hour 45 minutes to 2 hours 15 minutes with traffic and a quick stop. The coastal route is scenic but slower than the highway, especially through towns and around Brunswick and Wiscasset. In Rockland, use the downtown public lots or street parking near the harbor; avoid delaying too long, since you still have the lighthouse walk and a drive to Bar Harbor ahead. Before leaving Portland, check Claws’s seasonal hours—many Midcoast restaurants reduce schedules in October.
Start at Rockland Harbor Park, where a 30–45-minute walk gives you a good sense of the working waterfront and the islands offshore. Then have lunch at Claws, a casual harbor-area stop known for Maine lobster rolls. Ask specifically for warm butter on the side or poured over the lobster, since preparation can vary; budget about $25–40 per person and allow 60–75 minutes. This is the key meal stop, so call ahead if your arrival is late in the season and hours are limited.
After lunch, walk or drive a short distance downtown to the Farnsworth Art Museum for about 1½–2 hours. Its Maine-focused collection and Wyeth works are particularly worthwhile on a weather-softened October day, but seasonal opening days and hours can change, so verify the schedule before committing to the stop. From there, drive south to the Rockland Breakwater Lighthouse; parking is available near the start of the breakwater. The nearly mile-long walk each way takes about 1–1½ hours, and wind can be much stronger than in town, so bring a warm layer and skip it if conditions are rough.
Aim to leave Rockland by about 4:00 PM for Bar Harbor, taking US-1 and Route 3. The drive generally takes 1 hour 45 minutes to 2 hours 15 minutes, but October construction, low afternoon light, and arrival traffic near Bar Harbor can add time. Expect to park in town rather than directly beside your lodging, and allow extra time to find a space after arrival.
No packing list attached yet.