Rent a mountain bike from Rhinebeck Bicycle Shop (10 Garden Street; 845-876-4025; $25/day) and ride eight miles north the heavily wooded River Road, which traverses the back end of some of the area’s large riverfront estates. Follow the trail onto the leafy campus of Bard College and pause to check out the Fisher Center for the Performing Arts, a sculptural building of undulating silver canopies designed by Frank Gehry.
Pedal two miles south of Fisher Center to the Montgomery Place Orchards Farm Stand (Routes 199 and 9G; 845-758-6338), a market showcasing seasonal produce, cheese, grass-fed beef, and lamb from local farmers. Stock up on Doug and Talea Fincke’s renowned fruit jams and mason jars full of Annandale Atomic hard cider.
Take the East Tower route in Ferncliff Forest (845-876-3196), a preserve two miles outside Rhinebeck Village with eleven marked trails. Ride until you reach the scenic observation tower, which offers aerial views of the Hudson Valley and the surrounding Catskills.
Kayak through the tall reeds and purple loosestrife of Tivoli Bays, an estuary populated by snapping turtles, osprey, and muskrats (Hudson Valley Kayak Tours; 845-518-1455). Book the sunset tour (5 to 7 p.m.) to admire the riverscape at dusk.