Sip Pond Peninsula Trail at Chamberlain Conservation Area

This out-and-back trail follows the Cheshire Rail Trail along the southern shore of Sip Pond before branching off on its own, bringing you to the water's edge and a view of Mount Monadnock.
Trail Activity
Accessible Experience Walking Bicycling Snowshoeing Ungroomed cross-country skiing Horseback riding
1.6 miles, Round Trip
Fitzwilliam (NH)
Packed Earth/Dirt, Gravel/Crushed Stone/Cinder, Snow, Ungroomed
Permitted on leash
Other Activities


From the Chamberlain Conservation Area parking lot, access the Cheshire Rail Trail and follow it northwest for a little under half of a mile. This stretch of rail trail passes a boggy wetland section of Sip Pond where you may see flycatchers, migratory warblers or waterfowl, frogs, and turtles.

The start of the Peninsula Trail is marked by a yellow gate on the right and travels approximately 0.15 mile on crushed gravel before reaching an opening to the water. Up to this point, the 6-foot-wide trail is wheelchair and stroller accessible.

From here the trail continues on packed dirt another 0.15 mile to the tip of the peninsula, where there's a 180-degree view of Sip Pond and Mount Monadnock. (This section of footpath is not wheelchair accessible.) From the tip of the peninsula, retrace your steps to return to the parking area.

Other Information

Former landowner Craig Chamberlain had planned on building a house on the edge of this property, but when his wife passed, he decided against it. Instead, Craig thought land conservation would be a good option and a way to honor his wife, Karla. The Monadnock Conservancy purchased the property from Craig, and now welcomes the public to enjoy the trail and access the pond.

Trail Manager

For more information, visit the Monadnock Conservancy website or contact:

Monadnock Conservancy

Monadnock Conservancy
15 Eagle Court 2nd Floor
PO Box 337
Keene, NH 03431
Phone: (603) 357-0600
View website

Trail Tips

Leave What You Find
Avoid the introduction or transport of non-native species. Clean, drain, and dry water equipment when moving between water bodies.
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Trailhead Information

From NH-12 N: From the intersection of US-202 and Hwy-12 in Winchendon, Massachusetts, head north on Hwy-12 for approximately 3.8 miles before turning left onto Cross Road. At the end of Cross Road, turn left onto Old Turnpike Road. The parking area is on the right about 0.1 mile down the road. 

From NH-12 S: From the intersection of NH-119 and NH-12 in Fitzwilliam, head south on NH-12 for 4 miles before turning right onto Old Turnpike Road. The parking area is on the right 0.7 mile down the road. 

Click on a parking icon to get custom directions
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February 17, 2022
Camp and clean. Sorry I was looking for a more private form to offer this but it seems comment is the only way I can contact the landowners. I saw some debris along the trail both wood and litter and I need a place to camp and video survival skills teachings. I am very fluent in survival skills if you check out homesteaders hangout / Winchendon farms on Facebook, you will see a lot of the information I hope to display. I do hope to pay for the trash removal out of respect for letting me video. As well as hope to enjoy some of the awesome conversations we find on this trail..
If this is something you can agree to please message me back? As soon as possible. thank you..
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