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The Boston Hollow Letterbox

Placed: 5-25-02
Placed By: WWW (Formerly known as Chuck and Molly)
Location: Ashford, Connecticut, Windham County

Rated: Moderate, Terrain Difficult, steep hills and path alongside cliffs. Lots of uphill hiking. Over a mile and a half to box.

WARNING: Tough terrain. Sometimes dangerous. Not recommended for children.

Proceed north from the intersection of route 44 and 89 in Ashford until you come to a stop sign and blinking red light. See a white church in front of you. This area of Ashford is known as Westford. From the church, take a right onto Boston Hollow Road and proceed 1.6 miles which turns to gravel and find a parking area on the left which is capable of parking 4-5 cars. Park here for your starting point.

Boston Hollow Road is in an old fault line that has eroded over millions of years. The old road which was at the bottom of it was a public road , a stage coach road, and turnpike between Boston and Hartford

Great views along the trail and spectacular when Mountain Laurel is in bloom.

Follow the blue blazed Nipmuck trail, the same side as the parking area. The letterbox is alongside of the trail. I will give you 8 landmarks which you must pass to assure you that you are not yet at the box.

1. Cross an old stone wall.
2. You will pass a pile of stones on your right which were obviously put there by man not nature.
3. Pass another pile of stones on your right after going slightly downhill which were put there by man. 
4. Reach a spot called the overlook. There is no sign. It is a cleared out section, near a cliff with lots of small pieces of glass on the ground. This is 7/10 of a mile from your starting point and offers a great view. Path goes along a cliff, then bears right along the winding path away from it. 
5. Path goes down a steep rocky hill.
6. Come to a very small clearing with half a dozen evergreens and white birch trees at 260 to 280 degrees.
7. Walk along a ledge ridge with a drop at 120 and 300 degrees.
8. Quickly following the ridge is an intermittent stream. Look across the stream. You will see a large boulder with 2 other rocks leaning against it.

Cross the stream and take 8 steps uphill on the trail. Take a reading of 40 degrees and go to the spot between the large boulder and the second rock. Look down on the ground and find the letterbox covered with a couple flat stones and some pieces of wood.

Before you set out, please read the waiver of responsibility and disclaimer.

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