Find your way into Highland.

Highland is one of those places that quietly rearranges your day around the water and the ridge. From the moment the river takes hold of the view—its broad, muted surface cupped by bluffs and towns—you sense a simplicity that invites doing, not just seeing. Walkways and boat rentals line the shore; kayaks and canoes slip from outfitter docks into quiet coves. A morning boat tour can turn into an afternoon kayak or ferry hop, or a late-afternoon walking tour that threads together historic neighborhoods, coffee shops, and galleries. For the planner, Highland’s mix of boat rental and kayak options makes it easy to craft a half-day paddle or a full-day circumnavigation of nearby islands and estuaries. Beyond the river, the Shawangunk Ridge stands like a backbone to the region—rocky, wind-swept, and studded with trailheads that deliver everything from brisk walking tours to technical hikes. Bike rental and bike tours are common ways to connect ridge viewpoints with valley roads; for those who prefer a softer pace, a sightseeing tour or bus tour offers a curated view of the valley’s farms, orchards, and mountain silhouettes. Eco tours emphasize the area’s migratory birds and estuarine habitats, while city tours and walking tours of nearby Poughkeepsie or New Paltz layer culture on top of outdoor pursuits. Lodging options range from riverfront inns that wake you with the sound of water to snug B&Bs that feel like home-base for multi-day hikes. Practicality lives next to possibility here. Ferries and commuter services mean you can plan point-to-point travel without a long shuttle; boat tours provide local orientation and often a glimpse into the river’s history and industry. Those seeking solitude will find pockets of quiet on less-traveled canoe routes and early-morning kayak tours. Families and beginner adventurers will appreciate approachable water activities and short, well-marked hikes, while intermediate and advanced visitors can stack ridge traverses and long bike tours into a single, satisfying day. In Highland you don’t have to choose one kind of trip—combine a morning of water activities, a midday sightseeing tour, and an evening hike to make the most of this compact, diverse corner of the Hudson Valley.

Accessibility is a strength: the town’s riverfront is steeped in public access points, making boat rental and kayak pick-ups straightforward. Local outfitters handle gear and briefings so you can maximize on-water time rather than logistics.

Pair active days with cultured evenings. Walking tours and city tours reveal local history and architecture, while seasonal festivals and farm-to-table spots keep your downtime as engaging as your outings.