Forever Friends

Upton State Forest

Westboro Rd., Upton, Massachusetts

Park Information

This 2,600 acre forest offers multiple trail uses including hiking, bicycling, and horseback riding. Hunting is permitted in season.

Park Directions

Mass Pike west to Rte.I 495 south (Upton exit 21B) right off ramp, go straight 3.5 miles and take right onto Westboro Rd. Forest is 2 miles on the right.

For best results get a map at the information board next to the parking lot.

This search should take between 3 and 4 hours. It can be said to be a moderate hike, about 10 miles with occasional climbing. There are 4 letterboxes to this series.

This Letterbox Series is dedicated to two special ladies, Joyce and Holly, who have been friends for fifty years.

Once you have parked, head back toward the park entrance. Once at the gate, you will see the beginnings of the Rabbit Run Trail across the street. Look for a short boardwalk. Follow the Rabbit Run Trail, crossing two more streets before entering deeper into the forest. Loop back south, then east, and then again north. After a while heading north, you will see a small stand of white birch on the right side of the trail with a stone wall off to the left of the trail. Just after passing this stand, scramble over to the far side of the wall. Position yourself facing the trail, and locate a small tree (not a birch) with three blue slashes off to your right. Face that tree. The first letterbox lies at the base of the tree right behind you. Stamp in, leave your note, and rehide the box well.

Continue along the Rabbit Run Trail, recrossing two of the three streets, traveling along the Old Hopkinton Spring Trail for a while, and finally recrossing the third street. You are now on the Mammoth Rock Trail. As you follow this trail to Mammoth Rock (and it truly is a mammoth rock), you will come to an area where the trail makes a sharp descent to the right. Just before this descent, on the right side of the trail there is a very large boulder balanced on the ridge. The second letterbox lies beneath the southern end of a medium sized boulder next to the balanced one. Take care stamping in as this may be a busy spot.

Proceed to the Mammoth Rock and take a little time to marvel at its size. Continue along the Mammoth Rock trail, passing the Grouse Trail, until you reach the Loop Road. Turn left and follow the Loop Road to Dean Pond. Just north of Dean Pond there is a jumble of rocks filling the pine grove located in the apex formed by the Loop Road and the Dean Pond Road. Somewhere among these rocks is a large one with a small pine tree growing out of its top. From the west side of this rock, step off eight paces, approximately twenty-five feet, due west. The third letterbox lies under a large flat rock that is mostly covered with pine needles. Once again, stamp in and carefully rehide the box.

Now, go back up the Loop Road until you come upon the Whistling Cave Trail on your left. Take this trail to the Whistling Cave. (more like a whistling boulder in the middle of the trail). This area of the forest will be very rocky with a plethora of various sized boulders. Leaving the whistling cave, continue along the trail to the very next blue trail marker on a tree to your right. Five paces along the trail after this marker, you will see two trees that were once one leaning on a boulder on a bearing of 20 degrees from where you stand. The final (and the best) letterbox lies at the base of these trees behind some logs and leaves. Leave your mark, hide the box, return to the path, turn right and continue on.

You will cross a swamp, finding your own way, as the trail was totally flooded in April 2002. From here on the markings become faint splashes of paint. Never fear, just stay on the trail. You will soon come to a steep climb. At the top, the trail ends at the Park Road. Turn right and follow the road back to the parking lot.

Please let us know about your adventures finding these treasures.