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Loop, Park and Den Pond Road Loop

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Upton State Forest

Loop, Park and Den Pond Road Loop is a 3.3 mile heavily trafficked loop trail located near Upton, Massachusetts that features beautiful wild flowers and is rated as moderate. The trail offers a number of activity options and is best used from April until September. Dogs are also able to use this trail but must be kept on leash.

Length 3.3 mi Elevation gain 262 ft Route type Loop
Dogs on leash Kid friendly Hiking Horseback riding Mountain biking Nature trips Snowshoeing Walking Bird watching Running Forest Views Wild flowers
Description
Waypoints (0)

A slightly more rustic and less traveled path in the Upton State Forest. Loop Rd. is a wide easily traveled path through the woods that leads to Whistling Cave path. Whistling Cave path is much less traveled and more challenging with a number of small streams to cross and large rock formations (including Whistling Cave).

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Reviews (187)
Photos (134)
Recordings (215)
Completed (243)
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Sean Marien
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Hiking

Really nice well marked trails. Not very strenuous, but there is hardly a flat trail in the forest. Kids enjoyed the glacial boulder climbing.

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Ed Makin
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Hiking
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Benjamin Vincent
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Hiking

Great walking.

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Daniel Oliveira
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Hiking
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Bin Zheng
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Hiking

Quiet and well maintained. Lots of choice of smaller trails off the main road.

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Walison Rosa
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Hiking

Nice trail as always, easy and beautiful

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shiva theja
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Hiking
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Ben Crawford
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Hiking

nice but easy

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Benjamin Vincent
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Hiking

Nice as always. Took some of the side trails and enjoyed the day

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Izzy Siedman
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HikingBugs

Well marked with lots of interesting side trails to explore cool rock formations. Brought two dogs who enjoyed it very much though we did notice some owners had obviously not been cleaning up after their pets.

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Olivia Pendas
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HikingBugs
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Caitlin Mooney
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HikingMuddy

Not well marked, but very light traffic and clean.

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Paul Matthews
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Hiking

Nice trail, terrible pet owners Dog crap everywhere, dogs off lease and bags of dog crap left piled up in the parking lot. When I spoke with a dog walker about the lease law they said their dog had a collar/harness and that the lease wasn’t needed. Not true. I like dogs but I don’t like walking in dog shit or being rushed/barked at by off lease dogs in a public park. Haters going to hate but I’m just saying lease your dog and pick up their mess, your mom doesn’t hike this trail to clean up after you.

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Barbie Carr
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Hiking

Good trail for kids. Lots of people walking dogs.

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Kelven Santa
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Hiking

Lots of small ponds along the way, and one deep incline for a good workout, could also hear the wildlife during the walk, would definitely recommend!

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Alison MacDonald
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Hiking

This might be my new favorite spot! Lots of trail options, clearly marked. Saw a whole two people in the 2 hours I was there.

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Michael Flynn
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Hiking

A nice wide walking trail with hiking trail offshoots. I can see it being good for mountain biking and cross country skiing. The hill on Deans pond is the only short moderate part of all of the graded road parts, but all a nice walk. I would like to come back and explore some more of the single track side trails. Scenic this time of year!

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Barb Prescott
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Hiking

This is a great walk through the woods. I definitely prefer heading toward the pond via Park Road to Dean Pond Road and back Loop Road, rather than the reverse direction. Park Road has lots of loose rock, making climbing more difficult. Also, the climb up Park Road is almost a half mile long, with the corresponding half-mile descent. I prefer to do the steeper section during the first half of my hike. Loop Road consists of a lot of shorter ascents, with level stretches between. Overall, this is one of my favorite hilly walks, and I come here often.

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Barb Prescott
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Walking

This is one of my favorite 3 mile walks. Nice & shady on hot days. Beautiful foliage in the fall. Be careful after a hard rainfall, as the many cobbles and rocks on Park Road can be slippery. Pretty scenery, especially at Dean Pond.

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Jenn Carr
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Hiking
First to Review

Nice, no litter but a few dog poop bags ! Why pick it up only to leave plastic bag behind ? Otherwise really enjoyable. Whistling Cave trial was my favorite. Will definitely be back.

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Kenzie Leigh
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Hiking
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Carmen Moreno
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Hiking
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alex luvisi
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Hiking
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Anna Davis
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Hiking
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Kayla Manczurowsky
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Running
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Simone Brucato
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Hiking
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Jahan Dadlani
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Hiking
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Dan Flynn
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Hiking
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Danny Whitt
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Hiking
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Ram Krishnan
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Hiking
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