Where to Eat
Ciro & Sal's (4 Kiley Court; 508/487-6444; ciroandsals.com; dinner for two $75) dishes up Northern Italian specialties like Abruzzese, a sauté of fish, scallops, clams, shrimp, mussels, and squid. Head to Clem & Ursie's (85 Shank Painter Rd.; 508/487-2333; clemandursies.com; lunch for two $25) for fresh lobster with drawn butter.
Where to Stay
The eight-bedroom Red Inn (15 Commercial St.; 508/487-7334; theredinn.com; doubles from $225) has views of Provincetown Harbor from nearly every window. Among the eight units at the Inn at Cook Street (7 Cook St.; 508/487-3894; innatcookstreet.com; doubles from $180), an 1836 Greek Revival mansion, are two garden cottages.
"I love to take a ride through the dunes to deserted Back Shore; the view over Cape Cod Bay at sunset is unforgettable," says native Rob Costa, owner of Art's Dune Tours (4 Standish St.; 508/487-1950; artsdunetours.com; tours from $21).—Lucinda Rosenfeld
Small-Town Getaway in Chester, Connecticut
Mention Chester—a 16-square-mile patch abutting the Connecticut River—and you'll get a puzzled look, even from a born-and-bred Yankee. This hidden treasure has kept its low profile for more than 200 years. Behind the Victorian storefronts on Main Street, you'll find tiny boutiques selling Scandinavian toys, Italian pottery, and contemporary art.
What to Do
Meander over to the 25-year-old Chester Gallery (76 Main St.; 860/526-9822), which shows works by regional artists such as printmaker Richard Ziemann. For all things Swedish and German, head to Chez Manon (21 Main St.; 860/526-2554; chezmanon.netm), a cheery boutique with wooden music boxes and flower-patterned linens.
Where to Eat
At lunchtime, locals pack into the River Tavern (23 Main St.; 860/526-9417; lunch for two $60) for lobster-spinach bisque, and evening draws a smart cocktail crowd. The cozy Restaurant du Village (59 Main St.; 860/526-5301; restaurantduvillage.com; dinner for two $110) serves an Alsatian choucroute and an ethereal passion-fruit gratin.
Where to Stay
Six miles away, the 13-room Copper Beech Inn (46 Main St., Ivorytown; 860/767-0330; copperbeechinn.com; doubles from $195) has an airy atrium overlooking an English country-style garden, where croissants and waffles are served every morning.
"In the fall I like to pack a picnic and cross the river on the Chester-Hadlyme Ferry to Gillette Castle [67 River Rd., East Haddam; 860/526-2336], a 1919 hilltop mansion open to the public," Restaurant du Village chef and co-owner Cynthia Keller says.—Xander Kaplan
Historic New England in Keene, New Hampshire
The National Trust calls Keene "a Currier & Ives landscape come to life," which, if you disregard the skateboard park, is pretty spot-on. Keene's broad, elm-shaded Main Street has cafés, lively bars, and the landmark Colonial Theatre. In the fall, the surrounding countryside is just as big a draw: the Ashuelot River, rimmed by scarlet maples and traversed by rickety covered bridges; fragrant pine forests; and 3,165-foot Mount Monadnock, which has views clear to Boston, Maine, and Vermont.
What to Do
Cast for bass on Goose Pond, north of town (hike in from the trailhead on E. Surry Rd., off Rte. 12A). Then drive Route 12 northwest for 17 miles to Walpole, home to Ken Burns's film studio and Greek Revival architecture. Return to Keene via Route 10, a stretch of road with four covered bridges. In October, join revelers at the Pumpkin Festival (Oct. 20). Besides fireworks and pumpkin pie-eating contests, there are four looming towers of jack-o'-lanterns, each of which rises 40 feet above the town square.