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Woodbury Trolley Trail is a 3.7 mile lightly trafficked out and back trail located near Woodbury, Connecticut that features a lake and is good for all skill levels. The trail is primarily used for hiking, walking, running, and nature trips.

Length 3.7 mi Elevation gain 351 ft Route type Out & Back
Kid friendly Hiking Nature trips Walking Running Forest Lake Views
Waypoints (0)
Weather
UV Index
Daylight
Reviews (61)
Photos (62)
Recordings (78)
Completed (58)
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stuart ratcliff
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HikingBugsMuddyPrivate property

Not well marked at all terrible I thought I see one blue blaze and one blue w on a tree. I walked down to where the poster was about the trolley trail and then you see a red W so I went on that and did the long way round and yes you got a river which is nice and a pond. otherwise it needs some attention for blazes. and alot of trees down with this storm we had very rocky in places and not the best for winter by any means

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Chuck Bucchioni
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HikingMuddy

Folks, not sure where this map came from, it is not an accurate map of this trail. If you don’t mind walking along a lightly trafficked road you can turn this trail into a 3.19 mile loop, use the above map for where to park and then use my recording as a guide. The start of my recording is my driveway and I probably don’t have room for folks to park. I recommend doing the pavement part 1st as walking up Sherman Hill at the end of a 3 mile walk isn’t a lot of fun. if you park in the parking area on Old Sherman Hill road almost directly across from Trolley Bed road, take a left onto Old Sherman Hill road. Walk down the Sherman Hill, at the bottom of the hill take a left onto Middle Quarter road. When you get to the one lane bridge on your left you will see a fence with a trail behind it, take that left to begin the wooded part of the walk. For this recording I took 2 of the ‘walk arounds’ that have been created to avoid muddy areas of the walk. There are a couple of trees across one of the walk arounds so it’s not fit for biking.

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Chuck Bucchioni
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HikingMuddy

This is my "default" walk. I pretty much do it everyday. You can turn this into a 3.19 mile loop if you don't mind walking along the road. Suggest you do the road part first as climbing Old Sherman Hill is a bear as the last part of a 3 mile walk. If you park in the parking area on Old Sherman Hill road (almost opposite Trolley Bed road) take a left down Old Sherman Hill road (away from Trolley bed road. When you get to the bottom of Old Sherman Hill road take a left onto Middle Quarter road. Before you go over the one lane bridge you will see a small parking area on your left. Behind the little fence is this trail / the start of the wooded walk portion. There are muddy spots which can be easily negotiated. And actually those of us who regularly use this trail have created a number of ways around the mud, one takes you along the river. If you see me with my black & white APT (Pitbull) mix and my black lab mix, say hey

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Alecia Walkuski
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Hiking

Easy trail (only did the first half). The dogs enjoyed it. We saw four people in the hour we spent on the trail on a Sunday. We're looking forward to returning and hiking the whole trail

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Bill Lake
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Mountain bikingRocky

4 mile all purpose trail.The first trail is off of Scuppo rd and loops back on itself.This trail is called Trolley Dash.The second trail comes off off Trolley Dash and has about a 1/4 of a mile climb that switchbacks to Old Woodbury rd and it runs parallel along old Woodbury rd till it drops back down and heads back toward Trolley Dash.This Trail is called Off your Trolley.A total of 4 miles looping back to Scuppo rd.

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Caitlyn G
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HikingBugsMuddyPrivate property

Really fun trail! Great for all ages. It was private property on the other side of the river but that didn’t bug me. Also- speaking of bugs-there were so many bugs. We were constantly swatting them away. It was very muddy as well! It was a flat trail the entire way. It was about 1.5 miles.

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John Bates
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WalkingFloodedMuddy

Muddy for stretches. skirting some spots works well. work-around trails bypassi the worst stretches. a nice walk when the creek is running strong.

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Susan Vidal
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HikingMuddy

Steam running down parts of the trail.

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Victoria Foulke
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HikingIcy

Too icy yesterday to do this trail or the nearby Whittemore trail! Not worth a broken hip! Will return when it warms up and ice is gone!!

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Jim VanAmburg
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HikingOver grownPrivate propertyWashed out
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Desiree Vaiuso
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Hiking

NOT moderate. Easy.

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Nicole Perin
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HikingBugs
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Kevin Pimpinelli
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HikingBlowdownSnow

Easy trail. Small lake/pond at the end. Very icy today and great for dogs.

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Sonya Greenawalt
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Nice wide path, some large loose rocks though so take care not to twist an ankle. Lots of water & mud on the trail (Jan 1) but otherwise it’s hard to understand why this mostly flat trail was rated moderate difficulty. My hiking partner & I are relatively out of shape but considered this one of the easiest trails we’ve taken. We completed our leisurely hike in 38 minutes. There’s definitely a lake on the left at the end of the trail - if you’re following the right trail (there’s a trail that veers off to the right with a little bridge early on, that’s not the main trail).

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Ann MARIE Zinowich
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First to Review

We walked about an hour into the trail and did not find a lake. The trail was fairly flat and easy walking. No wildlife to be seen.

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Andrea Nilsen
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Hiking
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Caro Mac
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Hiking
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Deborah Garber
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Hiking
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Cady Greene
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Hiking
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Allicia Breton
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Hiking
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Lisa McHenry
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Hiking
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Elaine Matt
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Hiking
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