Laugh Til It Hurts  LbNA # 40186

Placed DateMay 31 2008
CountyNew Haven
LocationMiddlebury, CT
Planted ByTurtlesNest    
Found By PiscesGirl
Last Found Apr 29 2012
Hike Distance?

Laugh Till It Hurts

Trail Maintenance & Update 03/2009:
- We've had 9 groups of visitors and some great comments in our books. Thanks!
- All boxes seem to have survived the New England winter. Thanks for rewrapping!
- The Monkey House seems to be the hardest box to find but remember monkeys are shy creatures :)

This letterbox trail is an approximately 2½-mile walk through woodlands with some gentle slopes. It will take anywhere from 1½ - 2 hours tops. It starts at the South Street entrance to the Larkin Bridle Trail in Middlebury, CT.

Please email with any comments.

Interesting Facts
- The Larkin Bridle Trail is an old railroad trestle.
- Dayton’s Den is also located along the Larkin Bridle Trail.

#1 Monkey House
Park in front of green gate; while walking up the slope (heading west) count the wooden posts that are on both sides of the trail. You will pass 5 wooden posts. The monkey lives under the split tree with the vines growing on it on the right side of the trail. Open the door and reach in and get the letterbox.

#2 Pirate Den
Continue walking along the Bridle Trail. Find the tunnel that runs under the trail – enter from the right side and walk through the tunnel – on the right side of the tunnel find the pirates den in the rock wall. (If you reach the second green gate, then you have gone too far.)

#3 Octopus Lair
Come back up onto the trail – keep walking until you can take a right up through the woods along a trail (approximately ¼ miles). Go through a stonewall. There will be a BIG tree on the left side of the trail. Walk through 2 more stonewalls and continue up the hill past the woodpecker tree. At the top of the hill, the octopus lives in a stump near the stonewall.

#4 Laugh Till It Hurts
Continue along the trail with the wall on the left side – bear to the left at the top through the stone wall – bear to the right and follow stone wall along the right – the trail will gently slope down with a few birch trees on the left – go past a tree in the middle of the trail – at the Y in the trail, take a right - you will pass by an “asteroid rock” on the right – proceed to the wooden gate and open field – bear right – and stay to the right – walk down a grass path – go straight through or around the horse jump – go straight to the field. Stay to the left in the field and proceed by taking the path on the left – you will see a stone “tablet” on the wall to the left at the beginning of this trail– the fourth box is located behind the tablet.

Keep walking down the path until you meet the main trail. At this point, take a left and it will bring you back to your car.

Congratulations … hope you enjoyed the walk.