Aside from enjoying Wiscasset's handsome architecture and general quaintness, you can find several quirky, low-key attractions good for a break while traveling up along the coast, including the famed Red's Eats (see above). You’ll also find a handful of worthwhile antiques shops and eateries, as well as the excellent Wiscasset Bay Gallery (67 Main Street), displaying a trove of Monhegan Island landscape painters.
Boothbay Harbor (see below) was just another fishing village until it was "discovered" by wealthy city folks who built imposing seaside homes here. Once it embraced the tourist dollar, the village never really looked back, and in recent years it has emerged as a premier destination for tourists in search of classic coastal Maine; the village is often a mandatory stop on bus tours, which have in turn attracted kitsch, but some of the outlying areas remain beautiful.
Summer parking in the town requires either great persistence or forking over a few dollars. A popular local attraction is the long, narrow footbridge across the harbor, built in 1901. It's more of a destination than a link -- other than a few restaurants and motels, there's not much on the other side. The winding streets that weave through town are filled with souvenir shops purveying the usual trinkets.
In good weather stop by a Boothbay-region information center and request a free guide to the holdings of the Boothbay Region Land Trust (tel. 207/633-4818). More than a dozen of its properties dot the peninsula, most with quiet, lightly traveled trails good for a stroll or a picnic. Among the best: the Linekin Preserve, a 95-acre parcel en route to Ocean Point with 600 feet of riverfront. A hike around the loop trail (about 2 miles) occupies a pleasant hour. To find the preserve, drive south from Rte. 1 in Boothbay Harbor along Rte. 96 for about 3 3/4 miles, and look for the parking area on the left.
Boothbay Harbor is overrun with summer visitors, but at nearby Ocean Point, you can leave most of the crowds behind by following a picturesque lane that twists along the rocky shore past a colony of vintage summer homes. Follow Route 96 southward from just outside Boothbay Harbor and you'll pass through the sleepy village of East Boothbay before continuing on to the point. The narrow road runs through piney forests before arriving at the rocky finger. It's one of a handful of Maine peninsulas with a road edging its perimeter, allowing you fine ocean views. Colorful Victorian-era summer cottages bloom along the roadside like wildflowers. Ocean Point makes for a good bike loop, too; mountain-bike rentals are available from the Tidal Transit folks .
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.