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Bear Mountain is one of the best-known peaks of New York's Hudson Highlands. Located partially in Orange County in the town of Highlands and partially in Rockland County in the town of Stony Point, it lends its name to the nearby Bear Mountain Bridge and Bear Mountain State Park that contains it. Its summit, accessible by a paved road, has several roadside viewpoints, a picnic area and an observatory, the Perkins Memorial Tower. It is crossed by several hiking trails as well, including the oldest section of the Appalachian Trail (AT). As of 2021, the AT across Bear Mountain has been improved by the New York–New Jersey Trail Conference to minimize erosion and improve accessibility and sustainability as part of a project to rebuild and realign the trail that began in 2006. The Trailside Museum and Zoo located at the base of Bear Mountain is the lowest point on the Appalachian Trail (124 feet [38 m] above sea level). The steep eastern face of the mountain overlooks the Hudson River. The eastern side of the mountain consists of a pile of massive boulders, often the size of houses, that culminate in a 50-foot (15 m) cliff face at approximately the 1,000-foot (300 m) level. A direct scramble from the shore of Hessian Lake to Perkins Memorial Drive on the summit requires a gain of about 1,000 feet (300 m) in roughly 0.8 miles (1.3 km). From the summit, one can see as far as Manhattan, and the monument on High Point in New Jersey.

Bear Mountain State Park is a 5,205-acre (21.06 km2) state park located on the west bank of the Hudson River in Rockland and Orange counties, New York. The park offers biking, hiking, boating, picnicking, swimming, cross-country skiing, cross-country running, sledding and ice skating. It also includes several facilities such as the Perkins Memorial Tower, the Trailside Museum and Zoo, the Bear Mountain Inn, a merry-go-round, a pool, and a skating rink. It also hosts the Bear Mountain Circle, where the historic Palisades Interstate Parkway and Bear Mountain Bridge meet. It is managed by the Palisades Interstate Park Commission, which is overseen by the State of New York.

The Battle of Forts Clinton and Montgomery was an American Revolutionary War battle fought in the Hudson Highlands of the Hudson River valley, not far from West Point, on October 6, 1777. British forces under the command of General Sir Henry Clinton captured Fort Clinton and Fort Montgomery and then dismantled the first iteration of the Hudson River Chains. The purpose of the attack was to create a diversion to draw American troops from the army of General Horatio Gates, whose army was opposing British General John Burgoyne's attempt to gain control of the Hudson. The forts were garrisoned by about 600 Continental Army troops under the command of two brothers, General (and Governor of New York) George Clinton and General James Clinton, while General Israel Putnam led additional troops at nearby Peekskill, New York. (This battle is also sometimes called the "battle of the Clintons" because of the number of participants with that name. The brothers were probably not related to Sir Henry.) Using a series of feints, Henry Clinton fooled Putnam into withdrawing most of his troops to the east, and then he landed over 2,000 troops on the west side of the Hudson to assault the two forts. After several hours of hiking through the hilly terrain, Clinton divided his troops to stage simultaneous assaults on the two forts. Although the approach to Fort Montgomery was contested by a company armed with a small field piece, they attacked the two forts at nearly the same time and captured them after a relatively short battle. More than half the defenders were killed, wounded, or captured. The British followed up this success with raids as far north as Kingston before being recalled to New York City. The action came too late to be of any assistance to Burgoyne, who surrendered his army on October 17. The only notable consequences of the action were the casualties suffered and the British destruction of the two forts on their departure.

Fort Clinton was an American Revolutionary War fort erected by the Continental Army on the west bank of the Hudson River in 1776.

Fort Montgomery was a fortification built on the west bank of the Hudson River in Highlands, New York by the Continental Army during the American Revolution. Erected in 1776, Fort Montgomery was one of the first major investments by the Americans in strategic construction projects. Declared a National Historic Landmark, it is part of the Hudson River Valley National Heritage Area, owned and operated by the state of New York as the Fort Montgomery State Historic Site.

The Bear Mountain Inn is a 1915 hotel, restaurant and spa owned by the Palisades Interstate Park Commission and located in Bear Mountain State Park just south of the Bear Mountain Bridge in Rockland County, New York. It is now called the Bear Mountain Inn & Conference Center and features the 1915 Cafe and the Bear Mountain Trading Company gift store. A renovation was completed in April 2012.

Fort Montgomery is a hamlet (and census-designated place) in Orange County, New York, United States. The population was 1,627 at the 2020 census. It is part of the Poughkeepsie–Newburgh–Middletown, NY Metropolitan Statistical Area as well as the larger New York–Newark–Bridgeport, NY-NJ-CT-PA Combined Statistical Area. Fort Montgomery is in the southeastern corner of the town of Highlands, on U.S. Route 9W.

The Bear Mountain Bridge, ceremonially named the Purple Heart Veterans Memorial Bridge, is a toll suspension bridge in New York State. It carries US 6 and US 202 across the Hudson River between Bear Mountain State Park in Orange County and Cortlandt in Westchester County. At completion in 1924 it was longest suspension bridge in the world until this record was surpassed 19 months later by the Benjamin Franklin Bridge between Philadelphia and Camden, New Jersey. The Bear Mountain Bridge is unconventional among suspension bridges: though its main span (between the towers) is suspended by cables in the usual manner, the approach spans (outside the towers) do not have suspender cables and are instead unsuspended trusses, like the Williamsburg Bridge in New York City. The span enables connections between the Palisades Interstate Parkway and US 9W on the west bank near Bear Mountain and NY 9D on the east bank as well as US 9 and the Bear Mountain Parkway farther east. It also carries the Appalachian Trail and New York State Bicycle Route 9 across the Hudson. The bridge has two undivided vehicle lanes flanked by sidewalks. Cyclists may ride with motor vehicle traffic or walk their bikes on the sidewalks.

Highlands is a town on the eastern border of Orange County, New York. The population was 12,939 at the 2020 census. West Point, including the United States Military Academy, is located alongside the Hudson River in Highlands, and the military reservation occupies a large part of the town.

Doodletown was an isolated hamlet in the Town of Stony Point, Rockland County, New York, United States. Purchased by the Palisades Interstate Park Commission during the 1960s, it is now part of Bear Mountain State Park and a popular destination for hikers, birdwatchers, botanists, and local historians. It is located north of Jones Point, west of Iona Island, and southeast of Orange County. The former settlement is now a ghost town. Members of the first family to settle in Doodletown during the 18th century, Huguenots whose last name was anglicized to "June", were also the last to leave it in the 1960s.

Anthony's Nose is a 900+ ft (270 m) peak in the Hudson Highlands along the east bank of the Hudson River in the hamlet of Cortlandt Manor, New York. It lies at the extreme northwest end of Westchester County, and serves as the east anchor of the Bear Mountain Bridge.

Manitou station is a limited-service stop on the Metro-North Railroad's Hudson Line. It serves the hamlet of Manitou in the southwestern corner of Philipstown in Putnam County, New York. The station is open part-time, serving one weekday peak hour train in each direction and six weekend trains each direction. The Manitou station is one of three stations – along with Breakneck Ridge on the Hudson Line and Appalachian Trail on the Harlem Line – that receives limited passenger service. Like these stations, it serves mainly hikers visiting nearby state parks in the Hudson Highlands. There is no elevated platform and facilities at the station, one of two on the line adjacent to a grade crossing, are limited to a small shelter with the current schedule posted inside. The station predates the merger of New York Central and Pennsylvania Railroads.This station is the least used station on the Hudson Line, with only 42 passengers per week in 2018.