Sleepy Garrison takes full advantage of its riverside setting with a rambling waterfront park where pleasure boats dock at the marina, and a gazebo and willow tree–shaded benches are front-row seats to the mighty Hudson; across the shore, on the west bank, loom the buildings of the United States Military Academy at West Point. At Garrison's Landing, as the waterfront area is known, a small clutch of art galleries, offices, and homes surrounds the old train station, now a community theater called the Philipstown Depot.
Beyond the Landing, restored homes and artful landscapes bespeak the region's rich aesthetic history. Boscobel showcases architecture and decorative arts from the early-19th-century Federalist period, whereas Manitoga—the home, studio, and woodlands of industrial designer Russel Wright—fast-forwards into the mid-20th century. In summer the celebrated Hudson Valley Shakespeare Festival comes to town, gracing Boscobel with contemporary interpretations of the hallowed plays in a tent-theater. The Appalachian Trail also passes through the region, crossing the Hudson River at Bear Mountain and meandering through Garrison's many acres of protected land.