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.
Explore the remnants of the former 18th century settlement, Doodletown.
Private tour of the U.S. Military Academy at West Point.
Farm-to-Table lunch at the Bear Mountain Inn.
- 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.
- 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
- Cuisine: Lunch and Soft Drink Included*
- Adventure Activities: Hiking ~ 3 miles | 3 hours in duration
- Trip Activity Level: Easy**
- Packing List: Click HERE for a detailed Packing List
*Can accommodate dietary restrictions
**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.
- 8:45 AM | Arrive at New York City Pick-Up Location; Group Introductions
- 9:00 AM | Transportation to Bear Mountain State Park
- 10:30 AM | Begin 3-Mile Guided Hike on the 1777 Trail
- 1:45 PM | Lunch at the Blue Roof Tapas Room in the Bear Mountain Inn
- 3:00 PM | Private-Guided Tour on West Point campus
- 5:15 PM | Arrive at New York City Drop-Off Location; Tour Concludes
Please CONTACT US for more information.
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, New York
Settled in the 1800’s, 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 1960’s 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, New York
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.
United States 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.
- $149.00 per person
- $10 discount if you would like to meet group at Bear Mountain