Leaf Peeping

Scarlet Hill

The Scarlet Hill walk starts out in a gorgeous field with views of grazing horses. The field opens up into rolling hillsides with a speckling of trees. Take your time and examine the uncut grass to observe the many gorgeous wildflowers. There is a quick but steep path up Scarlet Hill that leads to an amazing overlook. This Eastward overlook has a view of the MIT Haystack Observatory and miles of trees. The view of trees framed by the faint outline of blue mountains coupled with a picturesque view of the stables, makes for a gorgeous walk.

Chestnut Hill

Chestnut Hill has a stunning Southeast overlook onto an expansive forest. There are two ways up to the top of this tall hill, a dirt road or a series of switchbacks through the wooded hillside. This is perfect for those who love the adventure of hiking new trails or those who get frustrated with dead ends. At the top of Chestnut Hill is a water tower and a flat grassy area around it. This is the perfect place stop, have a picnic, and gaze at the wonderful views that Chestnut Hill provides. Chestnut Hill would be the perfect place to get up and watch the sunrise. Chestnut Hill is the longest walk out of the three listed, but it is very rewarding.

Gibbet Hill

The Gibbet Hill walk is short, but steep. The walk up the hill takes less than 10 minutes with wonderful views at the top past the castle.

There is limited street parking. Please consider other locations for your fall walk during peak weekends in November, because it may be too crowded.

This is an enchanting walk up to a castle of stone and views that stretch for miles. After a quick climb up the hill an old burned down castle emerges. The castle is framed by seemingly ancient trees and a grassy hilltop. The castle is a wonderful place to have a picnic and watch the sunset, because there are places to sit and lots of shade. Shortly after the castle is a captivating westward view. The view looks across the lush green fields that fade into a forest of green in the spring and a fiery array in the fall. This view captivates the onlooker as houses, that seem to be painted on, peek through the trees. While standing at this lookout, the walker can watch the wind make the lush forest come alive and dance in a enthralling tapestry of colors. The truly picturesque lookout point on top of Gibbet Hill can truly be appreciated by all.