Highland offers easy access to the Hudson River and nearby mountains, making it ideal for outdoor lovers wanting hiking, paddling, bird watching, and seasonal winter sports. A great base for exploring the scenic Hudson Valley.
Highland offers easy access to the Hudson River and nearby mountains, making it ideal for outdoor lovers wanting hiking, paddling, bird watching, and seasonal winter sports. A great base for exploring the scenic Hudson Valley.
Outdoor Adventures in Highland, New York
Located on the east bank of the Hudson River, Highland, NY is a prime destination for outdoor enthusiasts seeking a mix of water and mountain activities in the Hudson Valley.
Book unforgettable outdoor adventures, guided tours, and gear rentals with verified Local Experts in Highland, New York.
Suggested tags reflect nearby experiences. Trips are shown nearest first when town coordinates are available.
⌖ 2.6 miA supported, 8‑hour, one‑way bike tour along New York’s longest car‑free trail—useful for riders who want logistics, refreshment stops and easy train access.
⌖ 3.9 miProspect Hill Orchards in Milton, NY offers school groups a lively orchard day with tractor rides, apple picking, and cider treats—a fresh approach to outdoor learning that connects kids to the harvest.
⌖ 3.9 miSpend a fresh fall day picking apples and pears at Prospect Hill Orchards in Milton, NY. Enjoy stunning views, diverse fruit varieties, and homemade baked treats at this family-run farm.
⌖ 3.9 miHarvest fresh peaches straight from the tree at Prospect Hill Orchards. Join the fun-filled picking season, enjoy homemade treats, and savor the taste of summer.
⌖ 4.2 miDiscover Hudson Valley’s scenic trails and craft beer on an 8-hour bike tour with Gotham Bicycle Tours. Perfect for outdoor lovers and history buffs alike.
⌖ 6.6 miA private 30-minute visit to spend time with shelter cats from Hudson Valley Animal Rescue and Sanctuary — book for up to eight people.
⌖ 6.6 miVisit Cats Lounge in New Paltz for a cozy, heartwarming encounter with rescue cats. Discover why this local favorite is a must-see for animal lovers and a great way to support shelter pets.
⌖ 7.7 miA focused, three‑hour guided tour through Ulster County that moves from historic New Paltz into working farms, an artists’ Glass House and the cliffs, lakes and waterfalls of the Shawangunks and Minnewaska preserve.
⌖ 11.1 miDiscover the charm of Lilymoore Alpaca Farm in Hudson Valley, where you can meet friendly alpacas, goats, and a mini pig. This guided tour offers family fun, education, and beautiful scenery just outside Pleasant Valley.
⌖ 11.1 miA concise, practical guide to Lilymoore Farm’s group alpaca and llama walking trek—what to expect, who it’s for, and how to prepare.
⌖ 13.9 miConnect with nature and each other on a romantic horseback Date Night ride at Juckas Riding Stables in the scenic Hudson Valley. Enjoy a twilight trail ride followed by a cozy fire pit gathering with charcuterie, s’mores, and drinks.
⌖ 14.5 miStep aboard Solaris, the Hudson River’s only solar-powered boat, for a 75-minute cruise featuring historian Bill Merchant’s captivating stories about the Delaware and Hudson Canal. This unique trip blends sustainable boating with immersive local history.
A two‑hour evening cruise from Kingston with live bands, full beverage service and shoreline views — this guide explains what you’ll hear, see and need to know before you board.
A narrated Hudson River cruise from Kingston that frames lighthouses, riverfront mansions and seasonal foliage—this guide distills what you’ll see and how to plan the trip.
⌖ 14.6 miA one-hour sightseeing cruise departing Kingston City Marina aboard the vintage 1930s Stroller IV to view Hudson Valley fall foliage, with beer, wine, cocktails and hot cider available for purchase.
Discover the unique natural wonders, summits, and scenic landmarks that make Highland, New York special.
★ 8.5⌖ 10.38 milesExplore the Labyrinth Trail near High Falls, NY. Enjoy bouldering and captivating views while hiking this challenging path. Ideal for adventure seekers, the best months to visit are spring and fall to avoid crowds.
★ 7.8⌖ 11.18 milesExplore High Falls in Upstate New York, a serene spot known for its stunning waterfall and scenic hikes. Enjoy nature walks and kayaking in a family-friendly setting. Visit in spring or fall for the best experience.
★ 8.2⌖ 11.56 milesEasyExperience the serene beauty of High Falls Waterfalls in High Falls, NY. With easy access and family-friendly paths, it's perfect for hiking, photography, and a quiet picnic. Best visited in spring or fall to enjoy vibrant foliage and cool weather.
★ 8.8⌖ 14.92 milesModerateExplore the waterfalls and cliffs of Minnewaska State Park Preserve near Kerhonkson, NY. This moderate hike features stunning views of quartz conglomerate cliffs, waterfalls like Awosting Falls, and serene lakes. Ideal in spring for water flow and fall for vibrant foliage.
★ 8.2⌖ 15.91 milesModerateExplore Beacon Overlook in Hudson Highlands State Park. With moderate trails and stunning views of the Hudson River, it's popular for hiking and photography. Watch for rare plant species and historical sites along the journey.
★ 7.2⌖ 19.80 milesModerateExplore Storm King Mountain in Cornwall, NY, offering moderate hikes with captivating views of the Hudson River. Birdwatching and photography opportunities abound. Best visited in fall for vibrant foliage. Located within Storm King and Hudson Highlands State Parks.
★ 8.5⌖ 19.94 milesModerateHike the moderate Howell Trail loop in Storm King State Park, Cornwall-On-Hudson, NY. Enjoy rocky granite formations, hardwood forests, and panoramic summit views of the Hudson River. This family-friendly trail offers birdwatching and nearby kayaking for a well-rounded outdoor adventure.
★ 8.2⌖ 20.20 milesHardExplore Hudson Highlands State Park, offering challenging hikes like Breakneck Ridge with panoramic views of the Hudson River. Enjoy kayaking for a serene river perspective. Best visited in spring and fall. Suitable for adventure seekers; expect steep terrain and historical sites.
★ 5⌖ 23.60 milesExplore Woodstock's natural charm and rich cultural history. Enjoy hiking in Catskill Mountains or kayaking along the Hudson River. With vibrant fall colors, it's a peaceful retreat perfect for adventure seekers.
★ 4.5⌖ 24.50 milesModerateExplore the varied terrain of Macedonia Brook State Park in Kent, CT. This moderate hike offers panoramic views and is popular for bird watching and fly fishing. Enjoy a serene escape among the rolling hills and vibrant foliage, especially stunning in the spring and fall.
★ 7.8⌖ 26.90 milesExplore Tory's Cave Preserve near New Milford, Connecticut, offering a unique spelunking adventure through limestone formations. Enjoy hiking and wildlife observation in this quiet and historic setting, especially during spring and fall.
★ 8.5⌖ 28.10 milesBear Mountain offers stunning fall foliage and hiking along the Appalachian Trail. Located near Highlands, NY, it's perfect for photographers and nature lovers. The park also features a zoo and museums. Best visited in fall for vibrant colors.
Make the most of your visit to Highland, New York with these essential planning tips, seasonal events, and protected lands.
Highland, New York hosts celebrated events throughout the year showcasing the region's culture, outdoor lifestyle, and community spirit.
Experience the vibrancy and unique outdoor heritage of Highland, New York during the iconic Hudson River Paddlefest. Plan accommodations and permits early.
Experience the vibrancy and unique outdoor heritage of Highland, New York during the iconic Shawangunk Mountain Festival. Plan accommodations and permits early.
Experience the vibrancy and unique outdoor heritage of Highland, New York during the iconic Hudson Valley Trail Days. Plan accommodations and permits early.
Highland, New York is surrounded by incredible protected natural lands offering pristine trails, wildlife habitats, and wilderness conservation.
Minnewaska State Park Preserve, located in the Shawangunk Mountains of New York, offers a stunning array of natural beauty and recreational activities amidst rugged terrain and scenic vistas.
Catskill Park is a stunning natural area in New York, offering diverse outdoor recreation including hiking, camping, and fishing in its varied landscapes.
Harriman State Park, located in New York, offers a vast terrain of forested hills and valleys, making it a prime spot for outdoor enthusiasts seeking hiking, camping, and wildlife observation.
High Point State Park offers stunning panoramic views from New Jersey's highest elevation point, with abundant outdoor recreation opportunities throughout the year.
Check weather for wind conditions if paddling on the Hudson River.
Wear insect repellent during warmer months due to mosquitoes near water.
Highland can be busy on weekends, consider weekday visits for a quieter experience.
Always check local regulations, fire restrictions, trail conditions, and weather forecasts before setting out on any adventure in Highland, New York. Respect nature, wildlife, and fellow adventurers by following Leave No Trace principles.