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Whipple Hill Loop

  4.0 ( 1 ) Favorite


2.4 mile 3.8 kilometer loop
95% Runnable


Ascent: 214' 65 m
Descent: -213' -65 m
High: 357' 109 m
Low: 183' 56 m


Avg Grade: 3% (2°)
Max Grade: 13% (7°)


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Trail shared by Zander Göpfert

A local favorite for a nice stroll through the woods or more aerobic workout to the highest point in Lexington.

Zander Göpfert

Features Birding · Views


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 run can be done in reverse or adapted with parking available at the southern and northern ends.

This loop run 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.

Need to Know

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.

Runner Notes

Great spot for a run with lots of elevation, rocks, and roots to keep a smaller area challenging.


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 run, 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).

Flora & Fauna

Northern hardwoods, white pines, songbirds.

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  4.0 from 1 vote
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27 Since Nov 12, 2019



Hiking up Whipple Hill. Photo provided by the Town of Lexington, Conservation Division.
Nov 14, 2019 near Lexington, MA
Whipple Hill pond. Photo provided by the Town of Lexington, Conservation Division.
Nov 14, 2019 near Lexington, MA
Early spring skunk cabbage" by tim t. (, Flickr licensed under CC BY-SA 2.0 (
Nov 12, 2019 near Lexington, MA
Looking up Whipple Hill. Photo provided by Town of Lexington, Conservation Division.
Nov 14, 2019 near Lexington, MA
Granite outcrop at the top of Whipple Hill. Photo provided by the Town of Lexington, Conservation Division.
Nov 14, 2019 near Lexington, MA


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