By late May, the Hudson Valley is fully in its outdoor season. Trails run green and shady, rivers open into long paddling routes, and old rail corridors hum with cyclists and walkers. This round-up gathers a range of ways to move through the landscape—from high overlooks to water-level explorations—mixing well-known destinations with quieter routes. The common thread is simple: get outside and let the terrain set the pace.
Kayak Bannerman’s Island
Bannerman Castle
Rising improbably from the Hudson River like a crumbling Scottish fortress, Bannerman Castle is one of the valley’s most surreal landmarks. Built in the early 1900s by arms dealer Francis Bannerman as a storage arsenal, the complex now stands in picturesque ruin on Pollepel Island. Paddlers launching from Beacon or Cold Spring can glide toward the island by kayak or canoe, passing rocky shorelines and watching trains snake along the opposite bank. The Hudson’s tidal current adds a bit of challenge, but the reward is a close-up view of one of the river’s strangest architectural fantasies.
Zipline Catamount Mountain
Catamount Mountain Resort
Straddling the New York-Massachusetts border, Catamount Mountain’s zipline tour launches riders across the Taconic ridgeline. The aerial course combines high-speed lines with scenic overlooks, giving participants a bird’s-eye view of the Berkshires.
Hike the Appalachian Trail
at Bear Mountain
Bear Mountain State Park
Bear Mountain holds a special place in hiking history: the first completed section of the Appalachian Trail was built here in 1923. The trail climbs stone staircases laid by early trail crews before scrambling across rocky outcrops with panoramic views of the Hudson Highlands. The hike is short but steep, gaining more than 1,000 feet in places. Early spring is an ideal time to visit, when the bare canopy reveals wide views across the river and deep into Harriman State Park.
Cycle the Walkway Over the Hudson
Walkway Over the Hudson
The Walkway Over the Hudson transforms a historic railroad bridge into one of the region’s most dramatic bike rides. Suspended 212 feet above the river, the mile-long span offers sweeping views of the Catskills, Hudson Highlands, and river traffic below. From the bridge, cyclists can connect to rail trails extending through both Dutchess and Ulster Counties, creating longer routes through forests, farms, and small towns. The smooth pavement and gentle grade make the ride accessible to casual cyclists.
Paddle the Rondout Creek
Rondout Creek
The Rondout Creek carries a surprising amount of history in its slow-moving water. In the 19th century it served as the eastern terminus of the Delaware and Hudson Canal, funneling Pennsylvania coal to the Hudson River and fueling the growth of Kingston’s waterfront. Today the creek feels far quieter. Launching from Kingston or Rosendale, paddlers drift past wooded banks, stone ruins, and broad tidal marshes where osprey and bald eagles patrol the skies. The current is generally gentle, making this an easy half-day outing with plenty of opportunities to explore quiet side coves.
Hike Storm King Mountain
Storm King State Park
Storm King Mountain rises abruptly above the Hudson River, forming one of the valley’s most recognizable silhouettes. The steep climb from Route 218 gains more than 1,300 feet before opening onto broad ledges overlooking the river and surrounding highlands. The mountain also helped shape environmental history: a proposed hydroelectric plant here in the 1960s sparked a landmark legal fight that helped launch the modern environmental movement. Today hikers enjoy the views thanks to that victory.
Hike Mount Greylock
Mount Greylock
Mount Greylock rises above the northern Berkshires as Massachusetts’s highest peak. Trails climb through hardwood forests and spruce groves to a summit crowned by the Veterans War Memorial Tower, built in the 1930s. On clear days the view stretches across five states. Herman Melville lived nearby and is said to have drawn inspiration from Greylock’s looming presence while writing Moby-Dick. Spring hikes reveal waterfalls and rushing streams fed by melting snow.
Bike the Ashokan Rail Trail
Ashokan Rail Trail
Running along the northern edge of the Ashokan Reservoir, this 11.5-mile rail trail offers expansive Catskill views and big-sky reflections across the water. The route follows the corridor of the old Ulster and Delaware Railroad, built in the late 1800s to connect the Catskills to the Hudson River. Today cyclists and walkers share the crushed-stone path, which offers a rare combination of flat riding and dramatic mountain scenery.
Paddle Canopus Lake
Clarence Fahnestock State Park
Tucked into the hardwood forests of the Hudson Highlands, Canopus Lake forms the tranquil heart of Fahnestock State Park. The 100-acre lake is sheltered from strong winds and edged by wooded shoreline, making it an approachable place for beginner kayakers and canoeists. Early spring paddlers often have the water largely to themselves, aside from the occasional great blue heron stalking the shallows. Trails radiate from the lake’s edge—including a nearby segment of the Appalachian Trail—so it’s easy to combine a quiet morning paddle with a leg-stretching hike through forests just beginning to leaf out.
Ride the Taconic Trails at Ninham Mountain
Ninham Mountain
Ninham Mountain in Putnam County offers a rugged mountain biking experience tucked deep in the Taconic foothills. The trails climb steadily through an oak forest before descending along rocky ridgelines and old woods roads. Riders who push to the summit are rewarded with one of the region’s more surprising views: a restored fire tower with sweeping vistas across the Hudson Highlands and into Connecticut. The terrain tends toward the technical—roots, rock gardens, and punchy climbs—making Ninham a favorite for riders looking to sharpen their skills. Spring rides here often include a chorus of returning songbirds echoing through the forest.
Enjoy rock climbing at Mohonk Preserve as it has climbs for beginners and expert climbers.
Rock Climbing at the Trapps
Mohonk Preserve
The quartz cliffs of the Shawangunks have drawn climbers for nearly a century. The Trapps area inside Mohonk Preserve offers hundreds of climbing routes ranging from beginner-friendly scrambles to classic multi-pitch ascents. The rock’s texture provides excellent friction, giving the Gunks their reputation as one of the most enjoyable climbing areas in North America. Even hikers enjoy the spectacle from the carriage roads below.
