Top 15 Things To Do in Highland, New York
Perched on the western bank of the Hudson, Highland is a compact launchpad for river days, ridge hikes, and low-key culture. This guide stitches together boat time and town time—think water activities and boat tours at dawn, a city tour or walking tour through small-town streets by midday, and ridge hikes or bike tours that finish with sunset over the river.
Top 15 Things To Do in Highland
Ranked by number of available trips • Each activity type links to all experiences
Why Highland Deserves a Spot on Your Hudson Valley Itinerary
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.
Best Time to Visit
Best Months
Weather Notes
Spring and fall bring the most stable weather for paddling and ridge hiking; summer offers warm water but afternoon storms can develop. Winters are quiet, with cold-water paddles possible for experienced, well-equipped visitors.
Peak Season
Late spring through early fall—weekends around summer holidays and peak fall foliage draw the most crowds.
Off-Season Opportunities
Late fall and winter weekdays yield lower lodging rates and near-solitude on trails. Plan for shorter daylight and check seasonal ferry or tour schedules.
Choose Your Adventure Level
Beginner
Short, well-marked walks and gentle paddles that require little gear or prior skill—ideal for families and first-time paddlers.
- Calm morning kayak on a sheltered river cove
- Walking tour of the riverfront and small-town historic district
- Leisurely bike rental along low-traffic roads
Intermediate
Longer paddles, ridge day-hikes, and mixed bike tours that require basic navigation and stamina.
- Point-to-point kayak or canoe route with a shuttle
- Half-day hike on Shawangunk Ridge to a sunset viewpoint
- Guided eco tour focused on birding and estuary ecology
Advanced
Full-day traverses, technical ridge scrambles, or multi-day paddles that require advanced planning, shore skills, and sometimes a guide.
- Full ridge traverse with off-trail sections and exposure
- Multi-launch kayak day combining ferry hops and open-river crossings
- Advanced bike tour over mixed terrain with significant elevation change
What to Bring
Essential
- Waterproof layers and quick-dry clothing for river time
- Personal flotation device (PFD) or plan to use one from the outfitter
- Traction footwear suitable for wet launches and rocky trails
- Sun protection (hat, SPF 30+, sunglasses)
- Reusable water bottle and snacks
Recommended
- Dry bag for phone, keys, and layers
- Light daypack for hikes and packing between put-ins
- Headlamp if you plan early starts or evening returns
- Map or offline route on your phone for self-guided walking or bike tours
Optional
- Binoculars for river and ridge birding
- Compact first-aid kit
- Action camera or small waterproof camera for paddling shots
Insider Tips & Local Knowledge
Confirm ferry and tour schedules, tide and river conditions, and trail access before you go.
Start early to beat afternoon winds on the Hudson and to secure parking at popular trailheads. For water activities, dress for immersion—temperatures can be colder on the river than on land—and use a PFD. If you’re renting a boat, ask outfitters for suggested routes that match your skill level and the day’s wind forecast. For ridge hikes, check parking restrictions and local preserve rules; consider a guided eco tour if you want interpretive context on flora and migrating birds. Finally, pair active days with neighborhood discoveries—short walking tours reveal local history and eateries where you can plan your next outing.
Frequently Asked Questions
Can I rent kayaks and canoes in Highland?
Yes—local outfitters offer boat rental including kayaks and canoes, and many provide shuttles or suggested loop routes for self-guided paddles.
Are guided boat tours and eco tours available year-round?
Guided boat tours and eco tours run primarily in spring through fall; weekend services and special seasonal runs may be limited in shoulder months. Check operator schedules in advance.
Is Highland a good base for both hiking and water activities?
Absolutely. Highland’s proximity to the Hudson and the Shawangunks makes it easy to combine hiking, biking, and water activities like ferry hops, boat tours, and paddles in a single trip.