AMBLEWAY Wildest hikes

Dogtown Conservation Land

FIRST ATTACKED–Never Try Never Win, 15 sights

8.4 mi · ▲ 144 ft · 2 hr 52 min

FIRST ATTACKED–Never Try Never Win, 15 sights is an 8.4-mile out-and-back in Dogtown Conservation Land near Pigeon Cove, MA. The route passes Bay State Quarry, Whale's Jaw, 20 and 8 more before reaching Strangman Pond at the turnaround, 4.2 miles in. It is mostly level, with 144 ft of elevation gain, and mostly dirt. It scores 17/100 on the Ambleway Wildness scale: paved and peopled.

Elevation

0 mi95 – 190 ft8.9 mi

Getting there

Trailhead: Unnamed 42.67353, -70.63504
Nearest town Pigeon Cove, MA
Google Maps Apple Maps

Directions

AMBLEWAYwww.ambleway.com

FIRST ATTACKED–Never Try Never Win, 15 sights

8.4 mi · ▲ 144 ft · 2 hr 52 min

Elevation 95–189 ft

Out & Back · Dogtown Conservation Land

Trailhead: 42.67353, -70.63504

Weather Sep 20: sunrise 6:28 AM · sunset 6:45 PM

Parking lot at the trailhead

  1. Start at the trailhead, heading NW.
  2. 0.4 miTurn left, heading W.
  3. 450 ftTurn left onto Old Rail Track, heading W.
  4. 450 ftTurn left, heading S.
  5. 50 ftPass Bay State Quarry.
  6. 0.8 miTurn right, heading S.
  7. 50 ftTurn left, heading S.
  8. 0.1 miContinue straight onto Anne's Trail, heading S.
  9. 0.2 miTurn left, heading SW.
  10. 0.1 miBear left, heading S.
  11. 0.1 miSharp right onto Common Road, heading SE.
  12. 0.5 miPass Whale's Jaw.
  13. 0.7 miTurn left onto Wharf Road, heading W.
  14. 0.3 miPass 20.
  15. 50 ftPass D.T. SQ.
  16. 50 ftPass D.T SQ.
  17. 150 ftBear right onto Dogtown Road, heading S.
  18. 0.1 miPass FIRST ATTACKED.
  19. 50 ftPass Never Try Never Win.
  20. 50 ftPass 17.
  21. 50 ftPass 18.
  22. 50 ftPass JAS MERRY.
  23. 50 ftPass 19.
  24. 0.6 miPass Strangman Pond.
  25. 150 ftReach FIRST ATTACKED, then turn around and head back the way you came.
  26. 0.7 miBear left onto Wharf Road, heading NE.
  27. 0.4 miTurn right onto Common Road, heading N.
  28. 0.7 miBear left, heading N.
  29. 0.5 miSharp left, heading NE.
  30. 0.1 miBear right, heading N.
  31. 0.1 miTurn right onto Anne's Trail, heading E.
  32. 0.3 miTurn right, heading NW.
  33. 50 ftTurn left, heading NW.
  34. 0.8 miTurn right onto Old Rail Track, heading N.
  35. 450 ftTurn right, heading N.
  36. 450 ftTurn right, heading N.
  37. 0.4 miArrive back at the trailhead.

Each distance is the walk from the previous step. Tap a step for a map of its junction.

Trail map, photos and weather for this hike: www.ambleway.com/hikes/lilja-pit-lilja-pit-out-back-13-lakes-13-km-33c8

Trail surface

80% dirt6% gravel14% unspecified

Weather

Sunrise 6:28 AMSunset 6:45 PM

Sunset

The best sunset spot on this hike is 0.4 mi in (~11 min). Leave by 6:15 PM for the 6:45 PM sunset. Back at your car by 7:11 PM — 3 min before dark.

More sunset hikes nearby

Good to know

  • Parking lot at the trailhead

Other ways to reach this destination

More from this trailhead

Hikes near Pigeon Cove, Massachusetts