Fall has arrived in the Hudson Valley, and its crisp, sunny weekends make Philipstown’s many hikes great attractions for locals and tourists alike. The Breakneck Ridge trailhead, located just north of Cold Spring, is a very popular choice; however, it’s currently closed until April 2027 due to construction, according to the New York State Office of Parks, Recreation, and Historic Preservation. But there are plenty of other trails to appreciate in the meantime! Whether you like challenging climbs or casual walks, this guide to the best hikes near Cold Spring will have something for you.
Bull Hill
Bull Hill is a strenuous climb. The full loop, starting at Little Stony Point and taking the Washburn trail, is 5.3 miles long according to Alltrails.com, but there are other shorter trails as well. Soon after starting the hike, you reach a peaceful rock quarry with trails through it and caves to explore, making it a good stopping point for a short walk. Then, the trail ascends steeply along a high ridge with a view of the Hudson. Back at the bottom of the hill, it passes the Cornish Estate Ruins before returning to Little Stony Point. “Bull Hill is good if you want a difficult hike,” said junior Ruby McCormick, “but it also doesn’t have to take very long depending on which trail you pick.”
Little Stony Point
Across Route 9D from Bull Hill, Little Stony Point is a collection of shorter, less strenuous trails. They lead to the top of an outcropping that overlooks the Hudson River, and then around the shore below it. This hike can be especially engaging for kids because the trails are short with a lot of variety, and there’s a cave to explore. “Little Stony Point is great if you want a quick, low-stress hike,” commented sophomore Leo O’Neil. “It’s often really busy with tourists, but the views make up for it.”
South Redoubt
The South Redoubt is a 0.7-mile hike according to Alltrails.com. At the top, as well as a view of the Hudson River, is a redoubt where American soldiers fought during the American Revolution. The trail is within the Garrison School Forest, so Garrison students frequently take field trips to hike it. “I loved the Garrison School Forest hikes,” reflected Junior Clara Gelber, who attended Garrison for elementary and middle school. “They were a nice and healthy way to take a break from schoolwork.”
Earl’s Chimney
This hike features the ruins of an old chimney, all that’s left of a historic house. It starts at the Moneyhole Mountain trailhead across from the Garrison Fish and Game Club. Then, after 0.9 miles, it turns onto the Chimney Top Trail and continues for 1.4 miles until you reach the chimney. Senior Lucia Petty commented, “The views are beautiful and I love walking there with my family.”
Mount Beacon
North of Cold Spring, there are various trails that climb steeply up Mount Beacon. At the top, there’s a retired fire tower that you can climb. Junior Una Lentz commented, “It’s already a really tall mountain, and then you can climb the fire tower on top. You get an incredible view of the Hudson River.”
Sugarloaf
Sugarloaf is a hill in Garrison shaped like a pile of sugar. The trail is 2.9 miles long, according to Alltrails.com, and moderately strenuous. Freshman Clara Schimming commented, “Sugarloaf is really cool because, in addition to a great view, there are cactuses at the top!”
