Shenipsit : Dark Hollow Brook to Flat Brook Falls

Blue Blaze Shenipsit Trail and Connecticut State Forest

in Glastonbury, CT


Trail Map         Trails: 5 miles       Rating: ★★★☆☆

This section of the Shenipsit Trail, north of Rt. 2 through a parcel of the Meshomasic State Forest is an interesting mix of old and new trail that passes the culverts under Rt.2, climbs a ridgeline, and has a short spur to Flat Brook Falls until reaching Diamond Lake Rd for a total of about five miles one way.


Heading north from the parking at the end of Tollgate Rd the trail parallels Rt. passing the Glastonbury Gun Range and then a group of cement pillars before reaching the infamous culverts under Rt. 2.  Over the last ten years there have been a few attempts to move the Shenipsit under Rt. 2 through the culverts instead of the long road walk around.  The DOT shot down the plan for a small ledge to run along the side of the culverts that would allow hikers a more direct route.  I explored the culverts in 2016 and think the plan is entirely feasible.

From here the trail turns north and heads into the forest quickly gaining elevation on rocky scrambles to a tiny overlook.  The forest changes ecosystems a few times as you follow this series of hills.  There is another forested overlook atop a high ridge though the view isn’t much.  Soon after you reach the very short spur trail to Flat Brook Falls.  I visited the falls in 2018 after Fall rains to see the cascades that drop about 30ft.

Another .6 miles up the trail reaches Imperial Drive, a designated CFPA parking area for the trail.  There is a tall curb to get to the parking area so it is better suited SUVs and pickups.  The next stretch passes a seemingly man-made earthen dam and pond until Diamond Lake Rd. Where a very brief road walk with an overgrown entrance takes you through a largely forgotten section next to a pond in the Grayledge Open Space.

Heading north: 0.3 mile road walk on Birch Mtn Rd to Garnet Ledge

Heading south: Dickinson Rd



Peter Marteka – Exploring Meshomasic State Forest’s Dark Hollow Brook Will Bring Out Your Inner Child (2013)

New England Waterfalls – Flat Brook Falls

Auntie Beak – Shenipsit Trail & Dark Hollow Brook (2017)

CTMQ – Shenipsit Section 2 (2010)

The information shown here is for general reference purposes only. gives no warranty, expressed or implied, as to the accuracy or reliability of this data. Parking in all areas, whether designated here or not, is at your own risk. is not responsible for any damage or loss to vehicles or contents.
Last updated June 11th, 2023

Visited 2145 times, 4 Visits today

Related Listings

Green Fall Pond


41.535437, -71.810033

Green Fall Pond Connecticut State Forest and Blue Blaze Trail 200 acres in Voluntown, CT Parking: Large lot near Green Fall Pond Rd, Voluntown, CT Trail Map … Read more…

West Rock Ridge State Park


41.337800, -72.965522

West Rock Ridge State Park Connecticut State Park 1,691 acres in Hamden, Woodbridge, and Bethany, CT Parking: Main parking near 1134 Wintergreen Ave, New Haven, CT if the gate… Read more…

Fifty Foot Cliff Preserve


41.790196, -72.212954

Fifty Foot Cliff Preserve Mansfield Town Park 102 acres in Mansfield, CT Parking: Small lot behind the Mansfield Historical Society at 954 Storrs Rd, Storrs, CT or from… Read more…