Home — Driving Itineraries: American Revolutin in the Hudson Highlands
The American Revolution in the Hudson Valley,
The Battle for the Continent That Won The War
Driving Itinerary

Explore three of the most important military fortifications in America
What You’ll See and Experience — #1
Background [Printer Friendly Version]
The Hudson Valley contains the spot that General George Washington came to call the “key to the continent.” He was referring to the Hudson Highlands. This short stretch of river became the axis around which the American Revolution pivoted. It is from here that Washington chose to limit British adventures. It was to here that Washington founded his most formidable defensive works. And it was from here that he retreated to lay plans to end the war.

Once the British took Forts Montgomery and Clinton in October of 1777, they understood the vulnerability of proceeding further up the Hudson and withdrew to New York City. Subsequently, Gen. Washington focused much of the Patriot energies in the creation and fortification of the Highlands. They created “Fortress West Point”, the most substantial and heavily provisioned of all Colonial fortifications.

The Thayer Hotel
Every weekend there's a reason to get away to the Thayer Hotel.

The Highlands contains the sites of nine interlocking fortifications and dozens of redoubts, look-outs and defensive positions. Chains and cables were thrown across the river in three locations to prevent British ships of war from making use of the Hudson. And the most important transportation routes between the colonies of New England and the Middle and Southern colonies cross the river in the Hudson Highlands.

Today you’ll visit at least three of these forts, walk their fortifications, tour their defensive battlements and experience for yourself the strategic positioning of each. From atop a mountain you’ll have an eagle’s eye view of the lay of the land from which you can understand, for yourself, the configuration of the Highlands.

Along the way we must by-pass a couple of locations out of the frustration of the limitations of time. But we encourage you to come back and visit them on another day.

Wear good walking shoes, get an early start and have a great day. You’ll be on a tour bus, walking trails and out on some rocky terrain. But you’ll have a great day!

Using this Itinerary [Printer Friendly Version]
All of HV/Net’s Driving Itineraries are broken into five distinct sections. Each has a purpose and each supports the other.

The first, this section, gives you a quick look at what you will be seeing and experiencing. We give you a quick overview and approximate time for the trip.

In this Itinerary, we have also put together as brief a historical context as we can to give you the necessary background information to allow you to appreciate what you will be seeing. Although not a comprehensive retelling of the events of the American Revolution in the Hudson Valley, it does give you a quick oversight of the strategic importance of the Hudson Highlands in the war.

We then provide you with a map showing the locations of the sites we are directing you to visit and the major roads you will be traveling on.

The third section introduces you to each of the sites you will be visiting. We provide you with information on what you will be experiencing, seeing and enjoying. We let you know of the hours of operation, entrance fees and other amenities and restrictions you will encounter.

The fourth section is a detailed set of driving instructions. These are very detailed so that you won’t get lost as you wend your way thru the Valley.

The last section is where we provide you with alternatives, suggested stops for food and shopping and alternative “Detours” that highlight points of interest. Depending on your driving speed, traffic and so on, these detours could be incorporated into your day trip, or can be the centerpiece for a return trip into the Hudson Valley.

The Battlements of
the Hudson Highlands
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Fort Lafayette, Verplanck’s (Verplancke’s) Point south of Peekskill on the East bank of the Hudson. British landed 22 Mar 1777 in Lents Cove near Peekskill, attacked Peekskill, encounter near Peekskill Creek. September 1777 British landed a force at Peekskill, burned barracks and stores.

Fort Independence, on Roa (or Rahway) Hook, east bank of the Hudson, oposite the entrance to Camp Smith. All trace of this fort was obiterated by the operations of a sand and gravel company in the early 20’s.

Fort Lookout, between Peekskill and Canopus Creeks, east of Camp Smith. In 1925 a clump of dead trees on the hill were inside the old earthenworks.

Fort Constitution, On an east bank island opposite West Point.

Fort Stony Point, West bank of Hudson accross from Fort Lafayette. Captured by British, starting point of attack 6 October against Forts Clinton and Montgomery. Later recaptured by "Mad Anthony" Wayne.

Forts Clinton and Montgomery, on west bank of Hudson south and north respecfully of the Popoloen Creek, accross from Anthony’s Nose, now directly adjacent to the Bear Mountain Bridge. British forces under Sir Henry Clinton attacked 6 Oct 1777 American forces Commanded by Generals George and James Clinton. The Americans were defeated, a desperate fight between Lake Sinnipink and the river (rear of Bear Mountain Hotel) gave the lake the name "Bloody Pond."
Fort Putnam, at West Point.

Another Fort Clinton at West Point on the Hudson.

Boom and Chain, across the river at Fort Montgomery to Anthony’s Nose, about where the Bear Mountain Bridge is now. Capture of Forts Clinton and Montgomery 6 Oct 1777 led to the abandonment of the American fleet and the British breaking through on 7 Oct 1777. The British went upriver as far as Kingston, which they burned. At this time a force was advancing from the North under General Burgoyne, to meet with the British fleet. The defeat and surrender of Burgoyne to General Gates in Saratoga on 17 Oct 1777 ended this threat. Recently a Revolutionary War gun emplacement site has been found near the base of Anthony’s Nose where the boom and chain would have been anchored.

Historical Context [Printer Friendly Version]
From the opening of the conflict between American Colonial forces in their fight for independence and the British, control of the continent in the north was recognized as of central importance. Early in the conflict in 1775, American forces attempted to invade and capture Canada, thereby denying Britain a base on its northern border. As the British engaged in the struggle, they raided and captured Boston then moved south taking New York City, from which the American forces under the command of General Washington retreated in near-panic, defensively battling through the lower Hudson Valley across into Pennsylvania.

As the war opened, King George’s armies held, with these two cities, the political, economic and geographic centers of America’s most populated areas. From this strategic position they were able to enforce an effective blockade of all Colonial ports making the only means of communication and transport for the Colonists via overland routes, as well as denying them easy access to European assistance. With the collected might of the British fleet based in New York harbor, the British were poised to hit anywhere on the entire coast of America.

Politically, England understood that if they could separate the firebrands of New England from the Middle and Southern colonies, the movement for independence would wither and die. Strategically the only way to accomplish this was via the abundantly favorable geography provided, control of the Hudson River.

Early in the conflict, Gen. Washington understood this dire circumstance. Yet he also understood the strategic advantage he already possessed by still being in control of the area. In order to seize control of the Hudson, the British must pass through the Hudson Highlands, an area of geography where the river is squeezed between high bluffs making several extreme turns in direction. By holding these high lands, the Colonial forces could effectively, and with little commitment of resources, block the British from northern incursions up the river.

On June 14, 1776 General Washington wrote to the Continental Congress, “The passage of the Enemy up the North River, is a point big with many Consequences to the Public Interest; one particularly occurs to me well deserving your attention, and to prevent which, I shall gladly give every assistance in my power…” In this correspondence he clearly states the threat, “[The British] may endeavour to seize those defiles in which case the intercourse between the two Armies, both by land and Water, will be wholly cut off; than which a greater Misfortune could hardly befall the Service and Army, I must intreat you, to take the measure into Consideration and if possible provide against an Evil so much to be apprehended.

On the same day in his letter to James Clinton giving Clinton command of the defenses of the Hudson Highlands, he writes, “As these are or may become Posts of infinite Importance, especially the lower one; I cannot sufficiently impress upon you the Necessity of putting them into a fit Posture of Defense, without Delay."

In September of 1776 in writing again to James Clinton, “I have this day wrote to the President of the Convention of New York, requesting that an Aid of Six hundred Militia may be sent to you from the Counties of Ulster and Orange, or any other that is more proper and convenient, for the purpose of assisting you, either in the defence of the High lands, in case they should be attacked, or of constructing New Works and Fortifications, by which they may be rendered more secure. However, whether you receive this Reinforcement or not, I must intreat you in the strongest manner to exert yourself to the utmost of your abilities in making these two posts [Forts Clinton and Montgomery] at the High lands, as defensible as possible. Their great Importance must be obvious to every person.

Meanwhile, on the British side, “Gentleman Johnny” John Burgoyne spent the early parts of 1777 in England promoting his plan for taking control of the continent, thereby ending the conflict. His proposal outlined his vision for defeating the rebellion by gaining control of the Hudson River, severing New England, “the head of the rebllion,” from the rest of the colonies. By taking control of the river, all communication between Northern colonies and those of the center and south would be cut off. An irresistible British force would be concentrated crushing all further opposition in New England, and with this done, the other colonies would quickly submit.

His plan was a three-pronged attack. He would personally command a large force of 7,000 from Canada proceeding south along the line of lakes in New York to the Hudson River, then proceeding down the banks of the Hudson to Albany. Meanwhile, another large force under command of Major Generals Clinton and Howe would advance north from New York City up the Hudson toward Albany. At the same time, General St. Leger would lead a diversionary force of 2,000 men eastward from Canada along the Mohawk River to link up with Burgoyne in Albany. The action would crush Northern Colonial forces causing a quick end to the conflict.

It would have worked. It was the action most feared by General Washington and the Continental Congress. But for two very different reasons, it didn’t work.

The first reason it didn’t work was caused by the hubris of General “Gentleman Johnny” John Burgoyne himself. Operating in the firm and uncontested position of having an undefeatable force, he allows himself to incorporate tactics that rather than defeating his enemy, inflamed them to action. He urged his Native American allies to acts of atrocity and barbarism that outraged the countryside. Instead of gaining the submission of the peoples he defeated, he drove them into opposition. As a consequence, he completely underestimated the growing strength of the forces rallying against him until it was too late, at the Battle of Bennington, (the battlefield located in the Hudson Valley in Renssealer County, not in Vermont), where his forces were routed.

The second, and more important reason the campaign didn’t work is that nobody bothered to order Major General Howe in New York City to participate.

Howe was off seizing Philadelphia!

By the time Howe got back to New York and half-heartedly engaged, Burgoyne was already essentially abandoned in the wilderness and on the verge of total defeat. He was approaching Saratoga Springs, his field of disgrace.

In October of 1777, Howe started his ascent of the Hudson, engaging the Rebel forces in the Highlands at Forts Clinton and Montgomery on October 6th. After a heated battle , he paused, sending only a small force of about 1,700 further north, stopping finally at Kingston, within forty miles of Albany, then retreating.

Meanwhile, General Burgoyne led his column to the attack at Saratoga the very next day, on October 7th. Neither General knew of the others situation. All Burgoyne knew was that he had received a communication that the attack from the south was finally in progress. In reply he sent word that he hoped the promised cooperation would be speedy and decisive, and added that unless he received assistance before the 10th of October he would be obliged to retreat to the lakes through want of provisions.

Instead, after engaging with the Colonial forces on October 7th and being firmly routed, he retreated to Saratoga and realized the futility of his position, surrounded by a vastly outnumbering force, ultimately surrendered to them. In this surrender, nearly one-third of British forces engaged on the continent were swept from the scene.

The other little thing it did was show that the Colonial forces could engage with, and win against the might of Britain.

It is doubtful that any single military event can be said to have exercised more influence over the future of a country than this complete defeat of Burgoyne and his plans. In failing, Burgoyne rescued the colonists from English domination and opened the door to France and Spain entering the conflict. Through this defeat, the conflict turned from one of the subjugation of rebellious colonies into a world conflict between the great powers.

The Highlands pivotal role in this conflict was in delaying British commanders Howe and Clinton from easily taking the Hudson from the south, causing them to pause and timidly proceed into the heart of New York, then retreating. By forcing the British to spend time and manpower in planning and executing the taking of the defenses of the Highlands, they caused the circumstance preventing the joining of forces from the south and north, stranding Burgoyne to his fate.

General Washington’s opinion that the defense of the Hudson Highlands was the “key to the continent” proved to be true.

After Burgoyne’s defeat, Colonial forces quickly regrouped and shifted their defensive focus of the Highlands to Fortress West Point. Learning from the past, they redoubled their efforts, creating defensive positions pinning the British in New York City, never allowing them again to ascend the Hudson River. The British shifted their focus to the south, ultimately suffering their worst defeat in Yorktown.

But that is another Hudson Valley driving itinerary. Were you aware that the success of Yorktown was formulated and implemented in the Hudson Highlands?


Driving Map — #2
Places You’ll Visit On Your Trip — #3
Perkins Memorial Tower
Bear Mountain Park
Bear Mountain, NY
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Where to Go, Play, Stay & Eat Nearby!

Possibly the most spectacular view of the river as it passes through the Hudson Highlands is to be had from atop Bear Mountaion at the Perkins Memorial Tower. Access to the tower is Free, but the hours are limited. At the time of this writing, June of 2004, the tower and surrounding grounds are only open on weekends.

Once you’ve reached the tower parking area you’ll find the tower and a series of short paths out to the point. From the point you can have a spectacular view south to New York City. Climb the tower and have a completely un-interrupted 360 degree view of 50 miles or more, depending on the day.
Once you have taken in these views, get back in your car and start to leave the tower area. Just past the parking area you will come upon an Exit sign pointing to the left. You want to take the road toward the right instead and head downhill. This will take you out to the eastern face of Bear Mountain and get you to the view previewed below. Follow the road and you will come upon a roadside parking area on your left. Pull in.

In all of the Valley, this is one of the choicest views providing you one of the most incredible vistas. From here you can see and appreciate the strategic importance of the Hudson Highlands.
In the image below we have labeled the sites that you will be seeing in closer detail today. You can see how each of these major sites is positioned to control access along the river. As the Hudson passes through the Highlands, it makes two major twists and turns. The first is as it enters the highlands through the “South Gate” out of Peekskill Bay. Forts Clinton and Montgomery are located on the west bank, just where the Bear Mountain Bridge is currently located, with a commanding position of the river and ships as they are forced broadside to make the turn.

The last and most important is from West point as the river makes two 90 degree turns. Forts Putnam and Clinton(2) are situated allowing them to control access along the river from this position. As ships are forced into this whirlpool and tightening series of maneuvers, it is impossible for them not to lay their flanks open to cannon fire from these forts.

As the British attacked Forts Clinton & Montgomery in October of 1777, they approached from the land, across the plain lying at your feet along the base of Bear Mountain. Hessian Lake, visible if you lean out, is the location of heated fighting as the Patriots valiantly fought to save the dual forts from falling into the hands of the British.


West Point
US Military Academy

West Point, NY 10996
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Where to Go, Play, Stay & Eat Nearby!

Now the location of the United States Military Academy at West Point, this high bluff commanding the approaches to the northern end of the Hudson Highlands was pivotal in the fight for American independence.

Early in the war, the Colonial Army put most of its efforts into the creation of Forts Clinton and Montgomery further south on the river. But after they were overrun by the British in October of 1777, the focus of the Highlands defensive positions shifted north to West Point.
“Fortress West Point” refers to a series of major fortifications reaching from Peekskill Bay up to Plum Point. The center of the command was from Forts Putnam and Clinton, (second fort with that name) located at West Point.

As you visit West Point via the tour bus, they will take you to what is now called “Trophy Point.” Sections of the original Great Chain that blocked the Hudson are displayed here. And from the overlook platform, you can see for yourself how the Colonial Army was able to control the Hudson from this most strategic location.

From Trophy Point, across the river is Constitution Island, site of Fort Constitution. Although a much lower bluff, when combined with Fort Clinton, roughly located on the point of West Point, and Fort Putnam, located atop the hill behind you, they formed an impregnable wall against which even the might of the British Navy couldn’t prevail.

To protect the river from the north, Washington had the cheveau de friese stretched between Plum Point and Pollopel Island, current location of Bannerman’s Castle. Pieces of this floating structure can be seen at Washington’s Headquarters in Newburgh. A chain and boom were thrown across the river from West Point to Constitution island as well, preventing shipping from slipping past the point.

Once the battlements were erected and fortified, the British were never again able to entertain the idea of seizing control of the Hudson River and thereby splitting the colonies. Had they been able to accomplish this, the war would have been lost to the Americans. The Hudson, and especially the Highlands, were the primary route of commerce and communication between the colonies of New England and the Middle and Southern colonies. Kings Ferry between Verplank and Jones Point in Peekskill Bay, was the principle crossing of the Hudson.

These days, visiting West Point is highly structured. As it is a functioning military post, and home of the oldest military academy in America, security has been drastically tightened since September 2001. Access to “the Point” is now strictly via tour buses from the Visitor Center just outside the gate in Highland Falls. The tour is an enjoyable ride allowing you to visit several locations on the base. The Visitors Center is open daily, with the exception of Thanksgiving, Christmas and New Year’s Day. Operating hours are from 9 a.m. to 4:45 p.m. Call (845) 938-2638 for information. Gift Shop's Telephone Number: (845) 446-3085. To take the tour, you MUST HAVE A PHOTO ID!

After your tour, take the time to visit the West Point Museum located just to the south of the Visitor Center. All visitors to the United States Military Academy are encouraged to tour the Museum to view what is considered to be the oldest and largest diversified public collection of miltaria in the Western Hemisphere. There are many displays and thousands of artifacts chronicling the history of the Army, from the Revolution up until today. Admission to the museum is free.

The West Point Museum is located directly behind the Visitors Center. The museum is in the renovated Olmsted Hall at Pershing Center on the grounds of the former Ladycliff College. The grounds were purchased by West Point after the college closed in the early 1980s. The building is named after the museum's primary donor, Major General George H. Olmsted, Class of 1922.

The museum’s collections represent all major categories of military study from arms, cannon and artillery to uniforms, military art and objects reflecting West Point’s history. Originally opened in 1854, the West Point Museum is the oldest and largest military museum in the country. It contains some of our most interesting national military treasures and one of the finest collections of military small arms available for public viewing. Every American armed conflict is represented in the 135 exhibits. An additional gallery portrays the history of the United States Army during peacetime and its role as a formative nation builder of our country. West Point’s history during and after the Revolutionary War, as well as the institutional history of the Military Academy, are traced in the West Point gallery devoted to the school, the cadet and the officer. The museum also provides exhibits in Thayer Hall to support the Department of History cadet curriculum with exhibit themes which range from ancient to modern civilizations.

The West Point Museum is open daily, with the exception of Thanksgiving, Christmas, and New Year’s Day. Operating hours are 10:30 a.m. to 4:15 p.m. For additional information, call (845) 938-2203/3590.

Fort Montgomery State Historic Site
Route 9W
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Where to Go, Play, Stay & Eat Nearby!
Begun in February 1776 Fort Montgomery had three landward redoubts and river batteries while Fort Clinton (August 1776) had a battery and two redoubts. On October 6, 1777, in a diversion to draw off American forces opposing General John Burgoyne's expedition into New York from Canada, General Sir Henry Clinton led 2,100 Loyalists, Hessians, and Regulars from King's Ferry against the landward approaches of Forts Montgomery and Clinton. American Brigadier Generals Governor George and James Clinton had to defend the two forts with a garrison of fewer than 700 men. On the river five American warships protected an iron chain on wooden rafts and boom of ships' hawsers. Despite the gallant American efforts, the undermanned twin forts fell to overwhelming British attack by nightfall. While British forces won the battles of Forts Clinton and Montgomery, these fortifications disrupted Sir Henry Clinton's timetable, complicating any attempts to relieve Burgoyne's trapped army.

Fort Montgomery comprises some twenty-five archeologically significant features on 14.42 acres of land owned since 1914 by the Palisades Interstate Park Commission. The ramparts of the irregularly shaped fortification follow the contours of the bluffs overlooking the Hudson River and Popolopen Creek and connect three landward redoubts-South, Round Hill, and North--and three river batteries-Grand, Putnam's, and River. Foundations of structures in the fort include the guard house, the powder magazine, the main barracks, officers' commissary, officers' barracks, storehouse, bake house, soldiers' necessary, provision stores, soldiers' hut and an additional barracks. A trail and interpretive signs tell the story of the fort and the battle. Fort Clinton has a museum with artifacts and exhibits describing the forts and the battles as well as the remarkably well-preserved Outer Redoubt.

Stony Point Battlefield
Park Road
Stony Point, NY 10980
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Where to Go, Play, Stay & Eat Nearby!

The British had captured the peninsula of Stony Point in May 1779, and began to fortify it by cutting down trees, and by erecting an earthen fort and two barriers called abatis. In addition, two British ships offered extra protection, and the newly-captured fort at Verplanck's Point, across the river, could be signaled by rocket for reinforcements. The commander of the garrison at Stony Point felt certain that his defenses were secure, calling the new fort his "little Gibraltar."

Washington responded to Clinton's move by marching his troops north from Middlebrook, New Jersey, to protect the American fortifications at West Point. Clinton garrisoned Stony Point and Verplanck's Point with about 1,000 men to protect the King's Ferry, which crossed the Hudson River between the two posts. Clinton then launched raids against Connecticut coastal towns, in the continuing attempt to lure Washington into battle.

Clearly, the British could not be allowed to remain unopposed at Stony Point, and by early July, Washington observed the enemy works himself from nearby Buckberg Mountain and devised a plan. Brigadier General Anthony Wayne would lead a surprise midnight assault against Stony Point. Wayne commanded the Corps of Light Infantry, a select force which probed enemy lines, fought running skirmishes, and defended the army against sudden attack. The Light Infantry was comprised of the very best soldiers, each regiment producing one company, which then served on detached duty.

The Battle on July 15, 1779, Wayne's troops began their march from Fort Montgomery, near the present-day Bear Mountain Bridge. For eight hours they struggled over narrow mountain trails, arresting civilians they encountered en route to avoid detection. When the soldiers arrived at Sprintsteel's Farm, two miles from Stony Point, they were told for the first time about their mission. One column of 300 men would wade through the marshes from the north. A second column, led by Wayne, would wade through the waters of Haverstraw Bay and approach from the south. Each of these two columns would consist of three parts: twenty men called "the forlorn hope" who would enter the enemy lines first, overcome sentries and cut through the abatis; an advance party which would enter the fort and seize its works; and the main body, which would continue around the unfinished back of the fort and approach it from the river.

Soldiers in these two attacking columns wore pieces of white paper in their hats to avoid confusion in the darkness, and were armed with unloaded muskets and fixed bayonets, so that an accidental shot would not reveal their presence and reduce the element of surprise. When they entered the enemy fort they would shout the watchword "the Fort's Our Own" to signal their comrades-in-arms. Finally, twenty-four artillery men would accompany the Light Infantry, so that captured enemy cannon could be turned against the British ships and their other fort at Verplanck's Point.

To create a diversion, a third column of two companies of Light Infantry would be positioned near the center of Stony Point peninsula and in front of the fort's defenses, where they would divert the enemy's attention by firing musket volleys. On a dark and windy midnight, the northern and southern attacking columns forded the marshes separating Stony Point from the mainland. The two columns swept up the treeless slopes, arriving in the fort within minutes of each other.

The heaviest fighting lasted half an hour, and by 1AM the garrison had surrendered. Fifteen Americans had been killed. Twenty British had also died, and the remainder were taken prisoners. "Our officers and men behaved like men who are determined to be free," reported Wayne, who received a slight head wound. Three days later, Washington abandoned Stony Point because he knew it could not be defended against the combined might of the British army and navy.

Although they returned to Stony Point and rebuilt the fort, British troops were withdrawn in October because of insufficient reinforcements, and never again threatened the Hudson Highlands. The victory at Stony Point was the last major battle in the north, and boosted American morale. Clinton's plan to defeat the Continentals and end the war had failed.

Detailed Driving Instructions — #4

The Thayer Hotel
Every weekend there's a reason to get away to the Thayer Hotel.

To start this Itinerary we are assuming you are leaving New York City or are arriving into the area via the New York State Thruway. From the City, take the George Washington Bridge and transition onto the Palisades Interstate Parkway. If you are arriving from the New York State Thruway, exit at Harriman, Exit #16, and transition onto Route 6 East, heading over the mountain. At the traffic circle, follow the signs for the Palisades Interstate Parkway North. Once you are on the PIP, VERY CAREFULLY AND VERY IMMEDIATELY get into the right hand lane as Exit #19 is just yards down the road. Alternatively, if you are coming from the east, you can take the Bear Mountain Bridge and enter onto the Palisades Interstate Parkway heading south and take Exit # 19.

Mile 0.0 – Ramp at Exit #19, (Perkins Memorial Drive), on the Palisades Interstate Parkway.

Mile 1.2 – Make sharp left turn onto Perkins Drive following signs to Perkins Tower.

Mile 3.3 – You have reached the parking lot for the Perkins Memorial Tower.

After returning to your car, exit the parking lot. As you reach the end of the parking lot, ahead of you there is an “Exit” sign pointing to the left. Instead of following this sign, follow the road as it turns to the right.

Mile 4.2 – On your left is a pull off area where you can park your car. Get out and look east for the view. When you are finished at this location and leave, make a “U” Turn and retrace your drive back up the road, this time following the exit signs when you get back to the area of the tower. The Exit signs will direct you to the right, back onto Perkins Drive and back down the mountain.

Mile 6.9 – You are back at the “Stop Sign” where Perkins Drive intersects with Perkins Memorial Drive. TURN LEFT. As you head east on Perkins Memorial Drive, make sure to watch the views on your right. There are several locations where the trees open up and you are presented with magnificent views.

Mile 8.7 – You have reached a VERY SHARP Hair-Pin curve. Just past the turn slow down as you enter the traffic circle. Follow the signs around the circle to the second right labeled “Bear Mountain, Route 6 & 9W.” On this road you will pass the Bear Mountain Inn on your left.

Mile 9.2 – Stop light just past the Bear Mountain Inn. Proceed straight ahead and transition from Perkins Memorial Drive onto Route 9W. A few hundred yards ahead you will encounter a traffic circle. Follow the circle straight across, the second right, following the signs for “West Point, Route 9W.” Continue north on Route 9W through the hamlet of Fort Montgomery.

Mile 12.4 – Follow signs for “West Point Visitor Center” and junction onto Route 218.

Mile 13.5 – Bear right following signs for “West Point Visitor Center.”

Mile 13.9 – Turn right into entrance of the “West Point Visitor Center,” and park your car. Enter the Visitor Center to purchase your tickets for a tour of West Point.

When exiting the West Point Visitor Center, turn left back onto Route 218.

Mile 14.7 – Stop sign. Bear left onto Route 218. Key Food Store is on your left.

Mile 15.6 – Carefully follow signs for “Route 9W South”. You will go over a bridge and follow the road as it bends to the left forming a ramp onto Route 9W.

Mile 17.4 – You are leaving the hamlet of Fort Montgomery. Get into the left lane and slow down or you will miss the next step!

Mile 17.9 – The road will be making a slow bend toward the left. As you come around the bend watch for an old sign for a “Trading Post” with an abandoned garage immediately adjacent to it on your LEFT. On your side of the garage is a gravel area, the “official” parking area for the Fort Montgomery State Historic Site. Pull in, park your car and walk south, in the same direction you were driving, to the Fort Montgomery site. It is 0.2 miles further down the road.

When you are finished with your visit at Fort Montgomery, exit the parking area turning left, south, onto Rouote 9W. Continue south, retracing your earlier drive. At the traffic circle, proceed around it turning right following the signs for “Haverstraw, Route 9W,” the second right. Drive south on Route 9W. You will pass the Bear Mountain State Park on your right. Further down the road, Iona Marsh and Iona Island is on your left. The road will turn into three lanes and you will head to the left and up hill. You are driving up, over and around Jones Point.

Mile 24.4 – You are entering the hamlet of Thompkins Cove.

Mile 26 – Slow down as things get just a little tricky finding the entrance road for Stony Point State Historic Site. There are two ways in, each end of “Park Road”. It is VERY poorly identified. However at about mile 26.5 you will see a BROWN SIGN on your right indicating the entrance is on the left. Slow down and turn left at your next opportunity onto Park Road. It can be very hard to see, so be careful and proceed slowly.

No matter which end of Park Road you are able to find, drive downhill and follow the signs for Stony Point State Historic Site. Drive through the gate, around the circle, under the Memorial Arch, over the bridge, down the road and into the Parking Area. If you have handicap identification, as you pass the cottage on the right take the road, driving around the road block, and drive up the hill to the handicapped parking area. If not, walk up the hill from the parking area to the museum, battlefield and lighthouse.

To leave, retrace your steps, proceeding straight ahead at the yield sign where you re-enter Park Road and drive uphill.

Mile 27.9 – You are at the Stop Sign where Park Road meets Route 9W. Turn left.

Mile 28.9 – You are at a traffic light. Turn right onto Route 210, “Central Highway”.

Mile 31.7 – Entrance for the Palisades Interstate Parkway, South, is on your left.

Alternate Destinations — #5
Woodbury Common Premium Outlets
Located at the junctions of Exit #16 of the New York State Thruway and Routes 6, 17 & 32 in Central Valley. As you can see from the road, Woodbury Common is a mega-center of factory outlets. At last count there were over 200 stores contained in the complex. It’s designed as a walking friendly colonial village with wide paved boulevards for the shoppers. If you've never been, it's definitely worth taking a day and doing some serious shopping. You might be interested to know that Woodbury Common is one of the most visited “tourist” sites in New York. To reach Woodbury Common from the area of this Driving Itinerary, at the Traffic Circle of Route 9W at Bear Mountain, take the Palisades Interstate Parkway. Follow the signs for “Central Valley.”

Located across the river in Putnam County. To reach Boscobel, from the Traffic Circle on Route 9W, take the Bear Mountain Bridge. At the eastern end turn left onto Route 9D, north. Follow it and Boscobel will be on your left after a few miles.

Venture into the 19th Century and experience life as it was in the days of the New Republic. Enjoy unsurpassed views of the Hudson River and West Point and see “the most beautiful home in America,” surrounded by exquisite formal gardens and meticulously kept lawns and grounds. Boscobel is a restored Federal period house overlooking the river with period furniture and decorative arts and gardens. Open daily except Tuesdays from 10 to 5. Tours available, last tour at 4:15pm.

Iona Island Marsh

Iona Island Marsh, as well as one of the best birding spots in the Hudson Valley, it has also been designated as a Registered Natural Landmark. It is one of the few remaining brackish water estuaries on the Hudson River.

Located just south of the Bear Mountain Bridge along Route 9W, past the Bear Mountain State Park Visitor Center, Iona Island Marsh is a quiet backwater, sleepily swaying in the summer breezes. Vast stands of cattails and other marsh reeds protect the fry of some of the most important game species of fish found in the Hudson. Kingfishers and cranes dive and stalk their prey through the reeds . Puffy clouds lazily float across the bright blue sky with the Bear Mountain Bridge in the background to the north.

It's a pleasant and very short drive down the road, through the marsh, to the gates of the Iona Island Naval Station, now closed to the public. If you've a NY State Fishing License, bring your pole and your bait and spend a quiet and lazy summer afternoon. Or just come out and walk the road, watch the birds angling for a meal, the hawks gliding through the sky and the songbirds scurrying about raising their brood.

Lunch Alternatives

After you visit West Point, it will almost certainly be early in the afternoon and you will undoubtedly be a bit peckish. We would suggest two alternative choices for lunch.

First, you are in the Village of Highland Falls, across the street from the downtown Village Center. Across the street are several interesting cafes and bistros for you to have lunch in. If you are into fast food, get back in your car and follow our driving directions to get to your next stop. However, as you drive through Highland Falls, on your left you will come to a Burger King franchise.

Or if you noticed an interesting little restaurant as you can north through the hamlet of Fort Montgomery, keep going and you will be driving right past it again.

Our second suggestion, and possibly our favorite. is to arrange something for a picnic at your next stop at the Fort Montgomery State Historic Site. As we mentioned, directly across the road from the West Point Visitor Center is the downtown Village Center of Highland Falls. There are several places where you can pick up some hot prepared foods or cold picnic fare. You can also follow our driving instructions and leave Highland Falls. When you reach the Stop Sign, we indicate that a Key Food Supermarket is to be found on your left, where you can pick up supplies for a splendid picnic.

If you do decide to picnic at Fort Montgomery, please be warned and aware that the site is a “Carry In, Carry Out” site, there are no facilities for your refuse and there is no water available. Fort Montgomery does have portable bathrooms on site for your use.

So plan ahead if you want to picnic at Fort Montgomery. Make sure to bring with you everything you will need, but as it is a brief although flat walk from the parking area, don’t weigh yourself down too much. And bring enough bags for you to pack your refuse into to carry back out with you. The view from the “Grand Battery” is one of the best in the Valley, so spreading a blanket on the ground and relaxing while you eat is a great experience.

If you are picnicking, make sure to keep something for later! At Stony Point, out at the lighthouse, the view is simply spectacular and having something to nosh and snack on as you sit taking it all in is a really great idea too!

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