Guides' Choice: The Great Escape

Upper West Side
Upper West Side
Broadway and West 76th Street
to 5:30PM
8:30AM to 5:30PM
Arrive by 8:15AM
9.0 miles
1,300 feet
elevation gain

Book Early & Save Price goes up $10 after Nov 19.
About the trip

In 1777, British troops devastated American Patriots at Fort Montgomery before progressing their troops around Bear Mountain. Two years later, American troops moved past Bear Mountain recapturing Stony Point, one of the Continental Army's most spectacular victories.

The Great Escape honors the troops from both sides of the war by retracing the soldier's footsteps. The trail starts with a steep climb over the peaks along the famed Appalachian Trail. Amid birch and maple forests, the path leads south until views of the Hudson Valley are presented. From this vantage point, you can imagine the British ships navigating the Hudson River, overtaking Stony Point.

As we make our way east, our route picks up the 1777 trail, the path created by the Colonials as they progressed north. The trail takes us to Doodletown, now an abandoned hamlet with only a few foundations remaining and an old cemetery.

Finishing our hike, we honor the Continental Army by taking the 1779 trail, the path created by the American troops. You can almost smell the gunpowder as you imagine the march of soldiers navigating the forest.

Share Trip
Level 6/10
1,300 feet elevation gain
9.0 miles
Upper West SideBroadway and West 76th Street
8:30AM to 5:30PMArrive by 8:15AM

Here’s what you need


Essential Gear
  • Lunch
  • Ample snacks
  • At least three liters of water
  • Backpack. Need a recommendation? Check out Deuter!
  • Weather-appropriate clothing. For a great selection and discounts, visit our partners
  • Sunscreen
Recommended Gear
  • Hiking poles
  • Gaiters


Essential Clothing
  • Comfortable athletic clothing
  • Waterproof hiking boots with non-cotton socks (required)
  • Hat
  • Jacket
  • Dress in layers to adapt to changing temperatures

Trip Package

  • Expert guides
  • Transportation
  • Park permits
Not Included
  • Meals
  • Gratuity for your guide

Drive to Meet

Have your own transportation? Select the "Drive to meet" option at check out. You'll meet your guide at the trailhead near Seven Lakes Drive at 9:15 AM.


Level 6


Level 6 trips will push you with a faster pace and longer distances. This hard work allows you to see more terrain and higher vistas. You should expect to be tired and fulfilled on the van ride home.


We’ll be active for five to eight hours. Prepare for this trip by maintaining your daily fitness regime that includes both cardio and strength.


Be ready to cover some serious distance. We may hike up to eleven miles today, nearly a half-marathon.


We’ll be hiking on varying mountainous terrain, which will involve navigating various rock faces, loose stones, and steep, uneven trails.


Up to 2,000 feet per day.


Up to 10,000 feet.


Weather conditions can be quite different from the city in the mountainous regions we visit. Temperatures can be quite cooler as we head north or to higher elevations. Keep your eyes out for an email from our team a few days in advance of your trip. That email will provide updated weather conditions and will alert you to anything additional you should put in your pack to prepare. We head outside in any weather, as long as we know it's safe, and we don't let a little rain or wind ruin a chance for an adventure. You can contact us at [email protected] if you have any questions about preparing for trail conditions.

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