Try a trail close to home — Gilmore Pond Trail
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My New Favorite Trail

By Kelly Reilly
Who’s to say you can’t have more than one favorite?  I discovered this while walking a new favorite trail of mine, the Gilmore Pond Trail.
What I appreciate the most about this trail, first, is its versatility; all within the Upper Jackstraw Brook Reservation, there are multiple trails that vary in length and scenery, allowing the hike to be tailored to a range of desires.
If you are looking for a short, easy, and serene walk, you can start from the Westborough Community Land Trust sign on Gilmore Farm Road or from the new entrance on Quick Farm Road.  After just about 0.1 mile, you will find yourself at the edge of Gilmore Pond, which in the peaceful sun is stunning and shimmery, like a hidden gem.  The trail loops around the pond for another 0.3 miles and then returns nicely to the beginning. 

If you’d like a little more distance, you can do what I like to do and start the Upper Jackstraw Trail from the WCLT sign at the Ruggles-end of Adams St., making the walk a round-trip total of 1.7-2 miles.  Through a large shaded forest, the trail leads over tiny streams with small wooden bridges and boardwalks, stirring in me childhood visions of grand adventures.  The trail leads alongside a house and across Gilmore Farm Road to meet the short pond-loop trail. 
In the end, I think what really makes this trail special is that, while in reality it cuts between streets and neighborhoods, you never feel that on the trail. The true and settling peacefulness of the place makes you forget entirely that there is a world just outside. 
Kelly Reilly has been walking local trails since she moved to Westborough in 1996.  She recently graduated from Colorado College with a degree in environmental policy.
A Favorite Trail at Gilmore Pond in Upper Jackstraw Brook Reservation
The Upper Jackstraw Brook Reservation is the largest property owned by the Westborough Community Land Trust (WCLT).  Its 53 acres include scenic Gilmore Pond, originally created in the 1930s as a fire pond when the surrounding area consisted of farmland and orchards. The pond is part of the headwaters of Jackstraw Brook, a major stream that feeds into Cedar Swamp Pond, where the Sudbury River originates. Today views of Gilmore Pond from the loop trail around it are a treat in all seasons, but especially in the fall. The pond is a “charm” on Westborough’s Charm Bracelet trail, which passes through the reservation (as Upper Jackstraw Trail).
Trail information
Location: Upper Jackstraw Brook Reservation, accessed from Gilmore Farm Road or Quick Farm Road (for the short Gilmore Pond Trail loop) or from Adams Street near Ruggles Street (for the longer walk on the Upper Jackstraw Trail).  Park at the side of the road near the WCLT sign at each place.
Length: about one-half (0.5) mile (Gilmore Pond loop); or about 1.7 – 2 miles (round-trip on the Upper Jackstraw Trail, from Adams Street near Ruggles Street).
Terrain: flat on the Gilmore Pond loop; gently uphill from Adams Street near Ruggles Street; can be muddy in places.
Trail map: Upper Jackstraw Brook Reservation Trail Map

A description of this trail walk from the trail map brochure: (Gilmore Pond loop) From Gilmore Farm Road, walk into the property on the Upper Jackstraw Trail. At 0.1 mile, you will come to Gilmore Pond. Follow the Gilmore Pond loop for 0.3 miles around the pond and return to your car by the Upper Jackstraw Trail. The total length of the walk is 0.5 miles.
(Round trip from Adams Street near Ruggles Street on Upper Jackstraw Trail) If you start from Adams Street, follow the Upper Jackstraw Trail through mixed hardwoods and cross one branch of Jackstraw Brook at a little over 0.2 miles. Continue on Upper Jackstraw Trail, and at 0.3 miles from Adams, take a right. Follow the wide corridor 0.1 miles to a sharp left turn into the woods. Head through the woods for 0.2 miles to Gilmore Farm Road, and follow the road to the beginning of the walk described above. After that walk, return as you came to your car on Adams for a total walk of 1.7 miles.
Noteworthy: Gilmore Pond is especially lovely in the fall, when its waters reflect the autumn foliage. In spring and summer, look for native wildflowers blooming here and there around the pond. Many of them were recently planted by a Girl Scout troop. Over the years, volunteer work parties and Boy Scout projects have worked to clear and control invasive oriental bittersweet, multiflora rose, and Asian honeysuckles.

Use a smart phone (I-phone or android) to access a phone app providing a tour of the wildlife and history of Gilmore Pond as you walk around the pond. You’ll first need to download the app

Many of the wooden bridges and boardwalks on the Upper Jacksraw Trail were built as Eagle Scout projects. A recently created short woodland trail (not yet named) now connects the Gilmore Pond loop with the next sections of the Charm Bracelet in Libbey Conservation Area and Wile Forest. This connecting trail is located at the southwest corner of the Gilmore Pond Trail (south of the Isaac Miller Spur trail).

For vicarious glimpses of autumn woods in the area, watch a Westborough TV video of a recent WCLT fall foliage walk that included the loop around Gilmore Pond as well as trails in Libbey Conservation Area and Wile Forest.

To download all the Charm Bracelet Trail Maps click here.
WCLT members and friends:  Tell us about your own favorite trail in town! 
Email us about it (300 words or less) at so we can add some trail information and share it with others.  Photos welcome!
Copyright © 2016, Westborough Community Land Trust, All rights reserved.
Our mailing address is:
PO Box 838, Westborough, Massachusetts 01581

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