Why Explore the Hudson Valley with TEP?
Explore the remnants of the former 18th century settlement, Doodletown. The village was closed in the 1960s, however, during the Revolutionary War British troops marched through its streets on their way to the battles of Fort Clinton and Fort Montgomery.
Enjoy a private tour of the U.S. Military Academy at West Point. Commissioned by General George Washington to protect the Hudson River from British advancements in New York, Fortress West Point was first put into operation in 1778. Its location was chosen due to its strategic position along the Hudson River, making it difficult for British ships to navigate.
Delight in a Farm-to-Table lunch at the Bear Mountain Inn. Built in 1915 and listed on The National Register of Historic Places, the Bear Mountain Inn is an upscale rustic mountain retreat.
Bear Mountain Adventure
The American Revolutionary War was at a critical juncture in October of the year 1777. General George Washington considered the site of a commanding plateau on the bank of the Hudson River to be the “Most Important Post in America” and directed for the establishment of a fort at this location. As British troops marched along the Hudson, Fortress West Point rose from the earth to become a symbol of strength and freedom for America.
- Hike on the 1777 East Trail in New York’s picturesque Hudson Highlands with the spectacular Hudson River in the backdrop.
- Explore the remnants of the former 18th century settlement, Doodletown, where British troops marched through on their way to the Battles of Fort Montgomery & Fort Clinton.
- Learn more about the history of the American Revolutionary War and America’s oldest war college on a private guided walking tour of the U.S. Military Academy at West Point.
- Enjoy a delectable lunch in the Blue Roof Tapas Bar while basking in the ambience of the historic Bear Mountain Inn.
Country: United States
Departure City: New York, NY
Pick-Up/Drop-Off Location: Upper West Side (76th and Broadway)
Duration: 1 day | 8:45 AM – 5:15 PM
Group Size: 6 – 11
Cuisine: Lunch included (can accommodate dietary restrictions)
Adventure Activities: Hiking ~ 3 miles | 3 hour duration
Trip Activity Level: Beginner*
*Please refer to our Trip Activity Level Guide or speak to one of our Adventure Consultants at 855-208-6800 to determine if this is the right trip for you.
Arrive at New York City Pick-Up location; Group Introductions
Transportation to Bear Mountain State Park
Begin 3-Mile Guided Hike on the 1777 Trail
Lunch at the Blue Roof Tapas Room in the Bear Mountain Inn
Private-Guided Tour on West Point campus
Arrive at New York City Drop-Off Location; Tour Concludes
Please CONTACT US for more information.
We conduct the General’s Fortress Bear Mountain Tour for private individuals and groups only.
To inquire on a custom date, please CONTACT US!
$249 per person
Bear Mountain State Park | New York
Bear Mountain State Park is located on the west bank of the Hudson River in New York. Comprised of over 5,000 acres, the park contains 3 mountains: Bear Mountain, Dunderberg Mountain, and West Mountain. A 6-mile section of the Appalachian Trail is also located in the Bear Mountain State Park making it one of the most popular hiking destinations in New York State.The area now known as Bear Mountain was of significant importance during the American Revolutionary War. Both the British and Colonial leadership considered control of the Hudson River to be of strategic importance towards winning the war and a number of important battles took place there.
1777 Trail | Bear Mountain State Park, New York
On October 6th, 1777, British General Sir Henry Clinton and his forces marched north from Stony Point, NY, and captured Fort Clinton and Fort Montgomery in the Hudson Highlands. Their historic march make up the 1777 trail in Bear Mountain. The east trail follows the path of the British troops who fought at Fort Clinton, and the west trail follows the path of the troops who fought at Fort Montgomery.
Doodletown | Bear Mountain State Park
Settled in the 1800s, Doodletown was an isolated village that was located in Bear Mountain State Park. It had over seventy homes along with a schoolhouse and church with nearly 350 inhabitants at its height. The village was closed in the 1960s and many of its buildings were destroyed; however, you can still see the remnants and original photographs of Doodletown while hiking past. During the Revolutionary War, British Troops marched through the streets of the village on their way to the battles of Fort Clinton and Fort Montgomery.
Bear Mountain Inn | Bear Mountain State Park
Built in 1915 and listed on The National Register of Historic Places, the Bear Mountain Inn is an upscale rustic mountain retreat with lodging, dining, and a full-service spa. Renovated in 2012, it boasts a long history of famous guests like professional sports teams, movie stars, and world leaders and is only steps away from the areas most popular hiking trails. Its restaurants offer the finest in culinary creativity with an emphasis on local and sustainable ingredients.
US Military Academy | West Point, New York
Commissioned by General George Washington to protect the Hudson River from British advancements in New York, Fortress West Point was first put into operation in 1778. Its location was chosen due to its strategic position which was along a narrow and S-shaped bend in the Hudson River making it difficult for British ships to navigate. In 1801, U.S. President Thomas Jefferson directed for the establishment of a military academy at the site of West Point. Housed on over 16,000 acres, the U.S. Military Academy at West Point remains to this day as one of the nations most elite educational institutions. Some of its famous students include Civil War Generals Robert E. Lee and Ulysses Grant. Approximately one thousand Army cadets graduate from the institution each year.