Start in Downtown Boothbay Harbor Waterfront, where the working harbor is at its most atmospheric in the morning. Allow about 45 minutes to follow the waterfront walk, cross the small footbridges, and browse the shops around Commercial Street and the harbor village. October is noticeably quieter than summer, but that also means some businesses keep reduced seasonal hours. Street parking is easier early in the day; bring a jacket, since the harbor can feel cold and breezy even when inland temperatures are mild. Continue on foot to Boothbay Harbor Memorial Library, a charming historic building where you can spend roughly 30 minutes looking through the local-interest displays and enjoying the quieter side of town. Check the library’s Friday hours before setting out, as fall schedules can vary.
Have lunch at Fisherman’s Wharf Inn Restaurant, right on the waterfront, allowing about an hour and budgeting approximately $25–45 per person before drinks and tip. The seafood-focused menu and harbor views make it a good fit for a short visit, but confirm its Friday opening hours in advance because late-season service can be limited. After lunch, drive west to Coastal Maine Botanical Gardens—roughly 15–20 minutes by car, depending on traffic and where you park—for 2 to 2½ hours among the seasonal displays, wooded paths, and Children’s Garden. This is the day’s main time commitment, so verify that the gardens are open on October 23 and whether timed admission or advance booking is required; admission prices are generally in the adult museum-and-garden range, with exact fall rates subject to change. Wear waterproof walking shoes, as paths can be damp and some areas are uneven.
Finish at Barrett Park in East Boothbay, about 15–20 minutes from the gardens. Give yourself 30–45 minutes for the short shoreline walk and the coastal viewpoint, which is especially peaceful late in the afternoon when the busier harbor has begun to empty. Parking is limited and conditions can be seasonal, so use the marked area and avoid blocking nearby residential access. If the weather turns wet or the gardens take longer than expected, keep Barrett Park brief rather than rushing the earlier stops; the appeal here is the unhurried view across the water, not a lengthy hike.
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