Exploring Wiscasset -- Aside from enjoying the town's handsome architecture and vaunted prettiness, you'll find a handful of worthwhile shops that range from sparely adorned art galleries to antiques shops cluttered with architectural salvage.
Exploring The Boothbay Region -- Summer parking in Boothbay Harbor 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 couple of unnotable restaurants and motels, not much is on the other side. The winding streets that weave through town are filled with shops catering to tourists. Don't expect much merchandise beyond the usual trinkets and souvenirs.
If dense fog or rain socks in the harbor, bide your time at the vintage Romar Bowling Lanes (tel. 207/633-5721). This log-and-shingle building near the footbridge has a harbor view and has been distracting travelers with traditional New England candlepin bowling since 1946.
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). Eight pockets of publicly accessible lands dot the peninsula, most with quiet, lightly traveled trails good for a stroll or a picnic. Among the best: Linekin Preserve, a 95-acre parcel en route to Ocean Point (drive south from Rte. 1 in Boothbay Harbor on Rte. 96 for 3.8 miles; look for parking on the left) with 600 feet of riverfront. A hike around the loop trail (about 2 miles) will occupy a pleasant hour.
Escaping the Crowds -- Boothbay Harbor is overrun with summer visitors, but at nearby Ocean Point, leave most of the crowds behind as you follow a picturesque lane that twists along the rocky shore and past a colony of vintage summer homes. Follow Route 96 southward east of Boothbay Harbor, and you'll pass through the sleepy village of East Boothbay before continuing on toward 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, which allows for fine ocean views. The colorful Victorian-era summer cottages bloom along the roadside like wildflowers. Ocean Point makes for a good bike loop. Mountain-bike rentals are available at Tidal Transit.
