Oak Hill is a 2.7 mile heavily trafficked loop trail located near Littleton, Massachusetts that offers scenic views 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.

Distance: 2.7 miles Elevation Gain: 370 feet Route Type: Loop

dogs on leash

kid friendly

hiking

mountain biking

nature trips

walking

bird watching

views

The yellow boundary trail is 3.3 miles long. It has a few hills and lots of nice, wide flat trails. The biggest obstacles are the rocks and tree roots.

hiking
muddy
rocky
1 day ago

Beautiful trail system with an amazing little lookout spot! I recommend! Lots of mosquitoes on wetter trails, both worth it. Some gravel wide paths and a lot of rocky steep and narrow trails. Tophet Chasm trail that I tracked was really muddy and buggy, with stepping stones that were hard to use.

hiking
bugs
1 day ago

Awesome - perfect cool overcast weather. The chasm is muddy but passable and buggy.

hiking
2 days ago

Very scenic and beautiful. Well marked. #littletongargoyle

hiking
muddy
rocky
5 days ago

it's a 2 beer trail. could have been a 3 beer but the doggo didn't want to go swimming. lol nice little creek, little waterfall. good all around moderate trail, bring some Off.

hiking
5 days ago

Good hike. Decent view. Went with three kids, 10, 8, and 9 months. Dog, too. No problems at all.

hiking
9 days ago

One of our family’s favorite trails we discovered on our non-stop hiking adventures during quarantine. And best marked trail we’ve encountered - really well done with the signage. You can’t get lost. We did the Tophet Chasm (yellow) 3.3 mile trail - 2 adults and a 4- and 7-year-old. Also brought our dog. I would not bring bikes for this age range. No way. Also, there is one spot for 5 minutes on the yellow trail that’s scary with little kids. Plan on going slow and holding their hands because it’s on the edge of a cliff. If you slipped it could be bad. Other than that part, trail is awesome and so diverse. Ups and downs. You’ll pass houses with decorations. There’s the “Littleton gargoyle” statue that the kids loved. And the lookout rock at the top is pretty. It is a long walk for a 4-year-old so we did carry her a few times. Took us 90 minutes with breaks along the way. We loved it!

recorded Oak Hill

hiking
muddy
10 days ago

Did the chasm side trail. Very muddy and steep.

hiking
rocky
12 days ago

Great hike for all levels. My 7 year old and I enjoyed the red/blue trail up to the overlook, then we took the yellow around the back of the mountain. Beautiful scenery.

hiking
14 days ago

Park at trailhead on Harvard Rd. Yellow trail with detour onto Red trail to summit from Lookout Rock. Good tromp through woods.

hiking
muddy
21 days ago

hiking
muddy
24 days ago

Highly recommend! Took our dog out for a little hike and the weather was perfect. The trails are mostly cleared. There were parts that was muddy but we just walked around it. Wasn’t hard at all and the high point was a nice stop!

hiking
26 days ago

was in the area and looking for a place to walk the dog, had no idea i’d stumble onto a place like this. what a beautiful place to get lost in. will definitely be back with more time to spend. not difficult at all and hundreds of ways to go.

hiking
muddy
1 month ago

hiking
1 month ago

Love it

mountain biking
muddy
rocky
1 month ago

Trails are rated differently for hiking and mtn biking. This was more than a moderate mtn biking trail. Would have been challenging for me solo but very difficult for my family of five, we pushed our bikes most of the way.

1 month ago

We took the yellow trail, 3.3 mile loop. Nice rolling hills, part of this trail has a steep drop off, may not be good for little kids under 4 unsupervised, but beautiful views at the end. People all respecting social distancing, and not overly crowded on the trail

took the letter boxing route. 10 boxes. kids loved it !!

hiking
2 months ago

Great local hike with a pretty fantastic view for very little effort. Some leftover snow and some muddy spots but in general dry and clear.

hiking
rocky
2 months ago

This was a great trail, with good views and good markings. Like another hiker said, this is 3.5 miles, not 2.7. It took us a little over an hour to hike. Part of the trail is along a very steep part of the hill and may be a little challenging on a rainy day. Another part of the trail is very close to residential houses, but most of it is well into the woods.

hiking
2 months ago

Great trail, first time going. took the dog, nice terrain with a great overlook. very clean. I recommend following yellow trail counter clockwise to get the most out of it!

hiking
3 months ago

The views at the top are amazing, almost a 5-star view. We took the yellow boundary trail and parts near the chasm were really icy and difficult.

hiking
icy
3 months ago

Nice trail. Well marked, nice view. It was icy today but not a problem with cleats

hiking
icy
3 months ago

hiking
icy
snow
4 months ago

hiking
muddy
4 months ago

Well marked, multiple trails with a good overlook. Great for a quick/easy hike.

hiking
snow
5 months ago

Oak Hill has a great network of trails. The woods were particularly beautiful covered in a few inches of fresh snow. Lookout Rock offers a spectacular view and the swamp is gorgeous. If you go through the bottom of Tophet Chasm, make sure you have good waterproof boots. There were lots of Ravens in the woods today as well!

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