Explore the most popular trails near Oakland with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

hiking

Oakland, Maine Map
VIEW FULL MAP
hiking
bugs
4 days ago

hiking
rocky
7 days ago

This is a great quick hike. I will do this as often as possible. it is well marked with blue blazes and well maintained. It is actually in Rome, not Oakland.

hiking
rocky
10 days ago

The description of this hike should include that there is an Outer Loop as well that is what is mapped here. We were a little pressed for time as this was our 3rd hike of the day and the rain was coming upon us, so we skipped the Outer Loop section and took the more direct route. There was some nice views on a very steep overlook that looked at Long Pond and Great Pond I think. We even saw a few Bald Eagles which was cool. Not doing the Outer Loop the hike ended up being maybe 1.8 miles but still a decent hike.

Good quick hike, we did this one directly after finishing the Mt Phillip Loop down the road. The trails are well marked and it had a nice view through a clearing up top that let you see a few ponds. Dog friendly and our dog loved it.

hiking
rocky
11 days ago

Good trail, perfect for going with your dog. We did it counter clock wise and that seemed like the best way if you have a dog with you. Pretty good marked trails, the loop back was a little hidden at the top but overall very good and awesome views of the Ponds at the top.

Did the loop twice with my wife and coonhound. Saw some vultures at the top.

hiking
13 days ago

Beautiful views.

hiking
14 days ago

I would have given this trail five stars if there was a view at the top but if you just need to do a trail and get into the woods this is great coming down I Followed a stream and they had a picnic area with a table in the center of the stream which was really nice

For a quick short hike the views were spectacular

hiking
17 days ago

Nice in the woods and hiking trail , dog friendly with stream running thru. Not a lot of open views , but simply beautiful.

hiking
24 days ago

good if youre local but not if its a drive

quick easy hike decent views very busy

hiking
rocky
29 days ago

1mi loop. Well marked and maintained. No scrambling but lots of rock to rock stepping. Fairly easy trail, good for kids and dogs. Look for two memorials - 1 rock seat near the summer, 2 plaques at the summit. Quick, fun trail.

hiking
bugs
rocky
30 days ago

Very nice short hike. Some parts were quite steep, but the rest of the hike was very mild. Well maintained and well marked. As we were sitting at one of the look outs, we saw two beautiful bald eagles that flew very close to us. Definitely a peek to the hike! I would definitely do this again.

Nice hike.. once at the top the view was nice but much of the scenic area was hard to see due to trees.. would definitely hike this trail again.

hiking
1 month ago

Great for kids, took 40 min to do entire trail with stops at the top. Nice lookout by summit, kids liked quick elevation gain for great view. Found a big toad and woodpecker

hiking
1 month ago

This was a very enjoyable hike. Everything was marked well until the loop. I suggest once you reach the pole line do an about face and follow the trail back out. The loop had nothing to see and was unmarked...

Nice and easy hike. Good views. My 70 lb. Coonhound loved it.

Beautiful trail until you get to the poorly marked (almost nonexistant!) loop!

hiking
1 month ago

Trail gps guide kept trying to correct my course saying I was off trail. I followed the marked trail, and when I followed the guide it led me through overgrown terrain and eventually off the trail altogether. Someone needs to do a refresher of this trail. Had constant misdirects from the app.

This is half of the trail. This side of the trail is more gradual & rocky. Beautiful views at the summit!

hiking
1 month ago

I’ve only parked at this trail once as I now live right down the road and usually just end up walking there. What I do remember is that there was more than enough parking space on the Kennedy Memorial Drive entrance. The trail itself is quite nice even with my young daughters in tow. The terrain is fairly navigable with only minor variations in elevation . There were a few bridges, one of which went over a small stream or creek. The trail loops lazily along the river for most of the first mile . At the end of that initial mile we were welcomed by a picnic table at which we enjoyed a delicious snack and some water. The path continues onward, never becoming too challenging although my three year old needed me to carry her the last mile.

hiking
1 month ago

Nice quick hike that can be done in under a half an hour. The peak is in the trees, although there are a couple beautiful views of Great Pond. The parking lot is not easy to find and always seems to be full. There is some space on the road to park.

hiking
1 month ago

Nice easy loop trail—basically a long walk in the woods. Not very steep. The Long Pond loop has a nice close overlook of the pond, but otherwise there is not much in the way of views on this hike.

hiking
1 month ago

Quick, easy hike with nice views of Long Pond from the top.

hiking
1 month ago

i just saw a bear here on the pond trail outer loop. 7/17 i ran

Great short trail with a nice view !

on Messalonskee Trail

hiking
2 months ago

nice hike through the woods next to the steam.

hiking
2 months ago

Really liked the trail once we figured out how to get to the parking lot. GPS had taken us up a private road that was near it. Major downside was ticks- one each for me and my husband, and three on the dog.

Load More