Shenipsit Trail: Dickinson Rd
Parking: Shoulder parking past 96 Dickinson Road, South Glastonbury, CT
Trail Map Trails: 6 miles Rating: ★★☆☆☆
This section of the Shenipsit Trail is contiguous with the southern terminus in that there is no defining feature/parking/or break between the two so it could be considered 1 nine-mile stretch between Gadpouch Rd and Dickinson Rd through parcels of the Meshomasic State Forest.
I ran this section south from Dickinson Rd and turned around about a mile shy of Bald Hill. This section follows old roads built by the CCC that often divide private land and state forest. First a dirt section of Dickinsin Road, then a rocky uphill section of Zeke Rd, then muddy Portland Reservoir Rd.
The first mile is well blazed with the new blue plastic bars, but beyond that you’ll need a careful eye for the faded paint blazes. Since the trails are old roads they are easy to follow however there are a number of junctions and forks that require minimal navigation.
There are no real highlights along this stretch so it’s just a peaceful walk in the woods on rolling terrain. The trail does appear to be used frequently by dirtbikes and ATVs and from the size of some of the tracks occasional heavy machinery.
Once you climb the forested Bald Hill, you’ll be in my section on the Southern Terminus.
The official route is a 2.8 mile road walk utilizing the paved section of Dickinson Road, Country Club Road, and Toll Gate Road to the Dark Hollow Section.
There is an abandoned stretch of trail here now largely hidden where the Shenipsit used to descend a rocky spine to Route 2 where you would run across both lanes.
The official route used to require crossing over Rt. 2 which was likened to Frogger. It was deemed too dangerous and the trail was rerouted with a road walk sometime around 2010. In 2015, the CFPA attempted to get a ledge built in the culverts under Route 2 to avoid the 2.8 mile road walk, but the DOT shot the plan down.
CTMQ – Shenipsit Section 1 (2009)
Peter Marteka – Autumn Is Amazing For Strolls On The Shenipsit Trail (2000)
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Last updated June 11th, 2023
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