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Bear Mountain, located in the Hudson Highlands of southeastern New York, is one of the most notable landmarks on the Appalachian Trail in the state. The AT crosses directly over the summit, which stands at 1,305 feet, which is not especially high, but it is a historically and symbolically significant summit; it’s home to the oldest continuously maintained section of the Appalachian Trail, built in 1923, and features wide stone steps and paved walkways constructed by trail crews and the Civilian Conservation Corps. For many hikers, Bear Mountain is also the site of the lowest elevation point on the AT, near the Hudson River just before the climb. From the top, you get sweeping views of the Hudson Valley, and the surrounding Bear Mountain State Park includes a lake, picnic areas, the Trailside Museum and Zoo (which the AT technically passes through), and access to nearby Perkins Memorial Tower. It’s a popular day hike, so don’t be surprised to share the trail with weekend crowds, especially in fall.

Bear Mountain peaks at just under 1,300 feet in elevation over a 4.5-mile stretch of picturesque paved road. Although it may seem small in comparison to some of the world’s renowned climbs, it makes up for this with stunning views of the Hudson Highlands.

The road makes a loop around the summit of Bear Mountain with the Perkins Memorial Tower at its center. From the top you get sweeping views south across the Hudson, Harriman State Park, and the route taken by the Appalachian Trail.

Highland Falls, situated in Orange County, New York, is a quaint village neighboring the renowned United States Military Academy at West Point. With a population of around 3,900, the village boasts a rich history intertwined with the academy's legacy. Its scenic location along the Hudson River and proximity to the Hudson Highlands State Park offer residents and visitors ample opportunities for outdoor recreation. With plenty of local shops, restaurants, and annual events, Highland Falls is a great spot for residents and visitors alike to relax after a long ride or hike.

Long Pond, renowned for ice fishing, beckons with chain pickerel and panfish. While largemouth bass are present, they tend to be on the smaller side. Enjoy the beautiful view of Long Pond Mountain.

Highland Falls, once Buttermilk Falls, transformed into a village in Orange County. Officially incorporated in 1906, it boasts a population of 3,684 as of 2020. Recognized for its suburban allure, the town is esteemed as one of the best places to live in New York, featuring numerous bars, restaurants, and coffee shops.

Popolopen Torne, affectionately known as “The Torne,” stands as a petite mountain within the Hudson Highlands, boasting a sharp, bald peak at 942 feet (0.29 km) above sea level and offering breathtaking views.

Long Pond, renowned for ice fishing, beckons with chain pickerel and panfish. While largemouth bass are present, they tend to be on the smaller side. Enjoy the beautiful view of Long Pond Mountain.