The Hudson Valley is vast and varied. With hundreds of miles of sandstone and granite cliffs, cattail-lined riverbanks, former factory towns, orchards, farmland and forests, the scale of its geography and the scope of its history are daunting. To spend a weekend dropping into its musty bookstores and sizable art institutions or idling between hilltop castles, divey small-town bars and doily B&Bs is like skipping a stone into a river: you bounce along, but barely break the surface. From New York City, it’s a one-hour train trip to Peekskill, at the doorstep of the mid-Hudson Valley, but the region can be fully explored only on the kind of road trip that skirts one side of the river and winds down the other, hopscotching between historic estates and detouring for farm stands, roadside diners and seductive swimming holes.

FRIDAY

4 p.m.

1. Peek Into Peekskill

Escape the city early and arrive in Peekskill in time for “hoppy hour” ($5 per 20-ounce pint; $1 raw oysters) at Peekskill Brewery, in a 7,000-square-foot space two blocks from Metro North. Equally worthy, the Birdsall House takes its name from a local boardinghouse frequented by George Washington; it has an antique cash register, live music on weekends and an excellent craft beer list. While in town, drop into Bruised Apple Books, with a section devoted to the Hudson Valley’s past and present, a pulp mystery reading room and a vinyl record listening station.

7:30 p.m.

2. Merci Beaucoup

In February, the Culinary Institute of America — a prestigious cooking school housed in a former seminary — opened the Bocuse Restaurant, replacing the institute’s original teaching restaurant, Escoffier, which closed last year after 39 years. The space has been reborn with a new name (a homage to the Lyonnaise chef Paul Bocuse) and an airy, bistro-style interior by Adam Tihany, who designed such celebrated Manhattan restaurants as Daniel and Per Se. The French menu includes Paul Bocuse’s 1975 recipe for black truffle soup with a puff pastry lid ($12), roasted rack of lamb with sunchoke purée and glazed vegetables ($28) and, Tuesday to Thursday, a three-course prix fixe dinner ($39) that’s an exceptional bargain.

10 p.m.

3. Folkies and Newbies

After dinner, backtrack to Beacon, home to the folk icon Pete Seeger, who founded one of the area’s largest music events: the Clearwater Festival (clearwaterfestival.org), staged in Croton-on-Hudson each June. A newcomer to town, Dogwood, opened in December in a wedge-shaped brick building near Fishkill Creek, serving adventurous cocktails like the Dutch’s Moonshine- and Luxardo Maraschino-based “Moondog” ($12). The combination cocktail bar, restaurant and music venue has fast become a local hangout to rival the house-made pirogies and charms of the vintage Main Street pub Max’s on Main. Alternatively, eat early and devote the night to music. Though the Band’s former drummer, Levon Helm, died over a year ago, the Midnight Rambles he held at his Woodstock studio endure as once- or twice-monthly hootenannies, which start at 8 p.m.