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The Magnificent 7: Part 2 - Family-Friendly Fall Hikes Near Blakeslee, PA

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5. Delaware Water Gap (Dingmans Falls)

Town: Milford, PA

Trail Length: 0.4 miles

Skill Level: Easy

Dog Policy: Not allowed on Dingmans Falls trail

Dingmans Falls – A Must-See Waterfall in the Poconos 🌲💦

Update: Closed for the 2025 summer season. Be sure to check the NPS website for the latest closure details.

When open, the journey to Dingmans Falls begins at the on-site visitor center, where a flat boardwalk trail winds through a shady hemlock ravine. 

Almost immediately, you’ll spot Silverthread Falls, a delicate 80-foot cascade slipping through a narrow chute.

From there, the boardwalk continues past rhododendron thickets and towering hemlocks before ending at the base of Dingmans Falls—Pennsylvania’s second-highest waterfall with a dramatic 130-foot drop. 

Visitors can enjoy the view from the lower platform or climb a short staircase for a breathtaking bird’s-eye perspective from above.

👉 Ready to make more lifetime family memories in the Poconos? Book your stay at Mountain Nest today.

6. Raymondskill Falls

Town: Milford, PA

Trail Length: ~0.3 miles

Skill Level: Easy to Moderate

Dog Policy: Not allowed on the falls trail

Raymondskill Falls – The Tallest Waterfall in Pennsylvania 🌊🌲

At three tiers high, Raymondskill Falls is the tallest waterfall in Pennsylvania, cascading dramatically along Raymondskill Creek. 

Visitors can take in the views from two platforms, one near the head of the fall,  and another at the large step that separates the upper drops from the lower. The trail to the top is especially striking as the water carves through the escarpment.

Looking for more? Just across the street from the parking lot, a short trail leads to Hackers Falls, another must-see waterfall in the Delaware Water Gap National Recreation Area.

🚐 Insider Tip: During the busy summer season (Memorial Day to Labor Day weekends), a free shuttle runs between the Milford Knob Trailhead and Raymondskill Falls, making it easy to enjoy the area without worrying about parking.

👉 Ready to make more lifetime family memories in the Poconos? Book your stay at Mountain Nest today.


7. Thomas Darling Preserve

Town: Blakeslee, PA

Trail Length: 2.2-mile loop

Skill Level: Easy

Dog Policy: Leashed dogs welcome

Thomas Darling Preserve – A Hidden Gem in the Poconos 🌲🐦

At over 1,400 acres, the Thomas Darling Preserve is the largest property managed by Wildlands Conservancy and one of the state’s most impressive spruce forests. This vast preserve is the result of conservation partnerships, with land owned by The Nature Conservancy and Tobyhanna Township and carefully managed to protect threatened bird species and their habitats.

Visitors will find a variety of short, scenic trails, each offering a unique glimpse into the preserve’s wetlands, woodlands, and wildlife:

  • Cerulean Trail (Blue, 0.7 miles): Under construction, this trail is being managed to support the cerulean warbler, a threatened bird species. Towering trees and dense vegetation create a peaceful canopy walk.
  • Whitetail Trail (White, 0.5 miles): Starting from the parking lot, this short loop winds through wetlands and uplands. In late summer, you’ll pass blackberry thickets and may spot deer resting in the evergreens.
  • Flying Squirrel Trail (Green, 0.5 miles): Wander through stands of hemlock and spruce where Northern Flying Squirrels nest. Wildlands monitors special nesting boxes along this trail.
  • Golden-Winged Trail (Yellow, 1.6 miles): This loop highlights over 50 acres of habitat managed for the golden-winged warbler. Listen for a chorus of birds, especially during migration season.
  • Prescribed Fire Trail (Orange, 0.7 miles): A unique walk through a forest shaped by controlled fire. Notice the resprouting vegetation, scarred bark, and fire access roads that tell the story of nature’s renewal.

Whether you’re birdwatching, walking among ancient spruces, or just enjoying a quiet escape into nature, the Thomas Darling Preserve is a special place to connect with the Poconos’ wild side.

👉 Ready to make more lifetime family memories in the Poconos? Book your stay at Mountain Nest today.