Whipple Hill provides a beautiful, natural escape for local residents and out-of-town visitors alike. With a well-maintained network of dirt trails and a good amount of elevation change, there are many options to explore this conserved parcel of land for groups of any size, age, or ability. The trails can be traveled in either direction and this hike can be done in reverse or adapted with parking available at the southern and northern ends.
This loop hike starts from the southern end parking off Summer St. and utilizes the outer trail sections on the west side up to the summit of Whipple Hill before returning past the vernal pool, Locke Pond, and the main trail thoroughfare along the seasonal stream back to the southern end.
Parking available on the Arlington side at Skyline Drive and Philemon Street, on the Lexington side at Summer Street, and the Winchester side at Winchester Drive with further access to/from Wright Locke Farm.
Wind through this protected parcel of woodland surrounding Whipple Hill past a seasonal stream, mature hardwoods, and exposed rock faces. The trails are marked with color-coded arrows for easy navigation with approximate distances to popular and helpful destinations.
For this loop hike, start at the Summer Street parking area in the south and head north on the ACROSS Lexington
trail toward junction 17. Turn left (west) onto the red-blazed Geology Loop (Red)
to begin the ascent toward the summit of Whipple Hill. When the leaves are down, the higher you get can afford nice views toward the Boston skyline to the southeast and Mount Wachusett to the west.
From the rocky summit, continue north toward the access trail for the Winchester parking area (Johnson Rd Access
) before taking a hard right turn at the northern entry point onto the ACROSS Lexington
trail down toward the vernal pool and Locke Pond, with Wright Locke Farm beyond it.
At junction 9, head left (east) onto the Farm/Wetland Loop (Yellow)
around Locke Pond, staying right at all junctions including number 10 for a brief connector toward junction 6 and the main trail thoroughfare to the left (southwest) back toward the main parking area. This stretch will be blazed in blue and yellow for the ACROSS Lexington
trail and Farm/Wetland Loop (Yellow)
Northern hardwoods, white pines, songbirds.