
Mass Public Peaks rank: #19
Elevation: 2,298 ft.
Prominence: 322 ft.
Isolation: 4.23 miles
Summit coordinates: 42°31’08.2″N 73°01’55.5″W
Town: Windsor, Massachusetts
Conservation Area: Notchview Reservation
Links:
Judges Hill on Peakbagger
Judges Hill on Listsof John
Notchview of Wikipedia
Notchview Reservation website, including trail map (Trustees of Reservations)
General info: Judges Hill lies within the Notchview Reservation in Windsor, Massachusetts, managed by the Trustees of Reservations. It is part of the Hoosac Range of the Berkshires. Judges Hill isn’t much of a climb due to the fact that this part of the Hoosac Range is rather like a long plateau instead of a ridge. The surrounding area maintains an elevation of around 2,000 feet, with Judges Hill rising as a modest “bump” on this elevated landscape. So you won’t need to be prepared for steep slopes. Instead, you’ll enjoy a beautifully maintained and historic conservation area with interesting trails, stone walls, pleasant woods, and wide open fields that were farmed not so long ago. The wooded summit features the ruins of an old lodge known as the “Judges Fort” (see history below). The large parking area and small visitors center are located off of Route 9 at 83 Old Route 9 in Windsor. The area is extremely popular for cross-country skiing, so hiking in the winter might involve some traffic on the trails. But in the early fall when I visited, I had the place virtually to myself.
Historical background: The Trustees of Reservations are known for preserving places of natural beauty and historical significance, and Notchview is no exception. Once a patchwork of small, hardscrabble farms in the 19th century, this area in Windsor transformed into a retreat for wealthy families in the late 19th and early 20th centuries. Judge James M. Barker of Pittsfield was among the first. In the 1890s, he purchased several properties, including Judges Hill. Barker and his Pittsfield friends formed the Windsor Club, building a clubhouse and, at the summit of Judge Hill, a picnic pavilion. While these structures are long gone, visitors can still see the stone remains of the pavilion, including a large chimney. General Alfred Bates of Washington, D.C., later joined the club, purchased adjacent land, and built a mansion. Eventually, Bates acquired Barker’s property, calling the combined estate “Highland Farm.” Many high society events took place there.
In the 1910s, Helen Gamwell Ely, a widow from Rochester, NY, purchased nearby farms and built her mansion, “Helenscourt.” In 1920, she married Lt. Col. Arthur D. Budd, a highly decorated World War I veteran. Budd retired in 1932, renaming the estate “Notch View Farm.” Over time, he acquired Bates’s “Highland Farm,” creating a sprawling 3,000-acre estate where he dabbled in agriculture, maple syrup harvesting, and trail building. When Budd died in 1965, he left the estate to the Trustees of Reservations. Today, the mansions and other buildings are gone, but the land retains traces of its storied past.

Recommended ascent routes:
Judges Hill, Saw Mill Field, and Orchard Loop: This recommended route on AllTrails is similar to the one I followed. Plenty of parking. The visitors center was closed when I was there (seems to be open more during ski season) but there are restrooms available there. Judges Hill was an easy climb, the ruins at the top were quite interesting. They must have had quite a view when this area was basically stripped of trees. I’ve noticed similar ruins at the top of many Berkshire hills–the foundations of small lodges with a stone chimney stack still standing. Must have been a tradition in this neck of the woods. The true highpoint seems to be right on the trail just slightly north of the ruins. This route will take you through Saw Mill Field which was my favorite part. Beautiful scenery–an expanse of dry, tall grass on an early autumn day and mountains beyond.
Nearby Listed Peaks: Judges Hill is relatively isolated, with no other “Mass 50 Highest Public Peaks” within hiking distance. However, if you have time for a second hike, Borden Mountain or North Mountain are both just a short drive away.
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