Top 15 Things To Do in Highland, New York

Highland sits on the Hudson’s western shore, a low-key launching point for everything from glassy morning paddles to open-river motor outings. Boat rental in Highland centers on easy access to wide riverwater, sheltered inlets, and scenic shorelines—making it an ideal base for first-time paddlers, families, and small-group day trips that link history, birdlife, and waterfront dining.

Highland sits on the east bank of the Hudson as a quiet staging ground for curated bus tours that stitch together river views, artful landscapes, historic towns, and seasonal spectacles. These guided drives turn short windows of free time into layered day trips—leaf-peeping in crisp fall light, spring apple-blossom runs, or slow summer crossings that pause at farmstands, galleries, and overlooks.

Highland's city tours are compact, layered strolls—riverfront promenades, small-town streets lined with independent shops and cafes, and a surprising number of outdoor vantage points where the Hudson and the Catskills frame the view. These urban walks shine for travelers who want an intimate, low-key exploration that combines history, contemporary craft culture, and access to nearby outdoor adventures like cycling, kayaking, and short hikes.

Highland’s hiking scene condenses the Hudson Valley’s variety into short drives: river-facing bluffs, wooded ridgelines, quiet marsh boardwalks, and quick summit views that reward minimal effort. This guide focuses on day hikes and half-day routes that reveal layered river vistas, seasonal color, and surprisingly wild terrain tucked just off Route 9W.

Highland sits on the Hudson's western bank as a quietly charismatic gateway to the Hudson Valley's trails, waterways, and small-town culture. Lodging here leans intimate: converted river cottages, family-run B&Bs, and farm stays that put you within easy reach of morning paddles, ridge-line hikes, and a surprising cluster of restaurants and craft producers. This guide focuses on where to rest—how places feel and function for outdoor days, seasonal considerations, access for active travelers, and planning notes to pair a stay with nearby adventures.

Highland's waterfront sits at a hinge of the Hudson Valley: a place where short ferry crossings translate rivers into routes, and where each departure offers a new way to move between miles of riverfront trails, village centers, and scenic overlooks. This guide focuses on the ferry experience — what it feels like, how to plan for it, and how to pair crossings with hiking, cycling, paddling, and food-focused outings nearby.

Highland sits on the eastern bank of the Hudson River where broad tidal flats, quiet side channels, and an immediate connection to the river’s storied landscape make for approachable—and surprisingly varied—kayaking. Expect reflective morning glass, bird-rich marshes, and paddles that pair easily with local hikes, the Walkway Over the Hudson, and riverside wineries.

Highland’s walking tours stitch together riverside vistas, industrial heritage, and surprising pockets of woodland—close to Beacon’s galleries, the tangle of old rail beds, and the slopes of Mount Beacon. These walks range from casual river strolls and historic neighborhood circuits to arts-and-architecture routes and steeper nature walks that lead toward panoramic overlooks. This guide focuses on walking as a way to slow down and layer nature, history, and local culture into a single afternoon or a multi-stop day of exploration.

Highland sits across the river from Poughkeepsie, where a collection of quiet backroads, riverfront greenways, and converted rail corridors create an unexpectedly rich arena for two-wheeled exploration. Bike rentals in Highland are the practical gateway: whether you want a relaxed e-bike loop along the Hudson, a gravel grinder through farmland and ridgelines, or a family-friendly ride onto the iconic Walkway Over the Hudson, rentals make it easy to match a bike to the terrain and the day’s ambitions.

Highland sits at a quiet edge of the Hudson Valley where tidal river flats, woodlands, and working farms fold into one another. Eco tours here are intimate, seasonal explorations — from marsh walks and bird-focused boat trips to farm-to-table habitat tours — that read the landscape at human scale and put conservation stories at the center.

Highland is a compact but surprisingly varied launching pad for bike tours that fold riverfront flatlands into sudden, steep climbs into the Hudson Highlands. Riders will find quiet country roads, riverfront paths, gravel backroads, and access to marked trails for mountain bikes—making the town an ideal stop for mixed-surface touring, day trips from the Hudson Valley, and loop rides that pair easy miles with short, rewarding climbs.

Highland, a low-lying town along the west bank of the Hudson, opens up a quietly rewarding canoeing playground: tidal river miles, protected backwaters, and short tributary runs framed by orchards, bluffs, and small waterfront hamlets. Whether you’re leaning toward a calm sunrise paddle, a day trip exploring river islands and eddies, or a gentle multi-stop excursion that pairs perfectly with farmstand snacks and a waterfront lunch, Highland offers approachable watertime with scenic payoff.