Four Ponds lies just east of Mooselookmeguntic Lake. The Appalachian Trail traverses the length of this 6,000-acre unit with a lean-to at Sabbath Day Pond and a campsite at Little Swift River Pond. Fishing and swimming are popular activities. Winter visitors pass through on snowmobiles on their way from Rangeley to Weld.

If you're looking for a challenging hike, this is the trail for you. it's well kept and very rugged. There are lots of tall stones and some climbing involved. I started on the loop trail to reach the summit and spent the night at the pond in a tent. The "chimney" is kind of like a tight, small cave you have to climb up 3 staples in large stones to get through. It's impossible to climb through with your backpack on your back so I'd advise to hike with a friend and have them reach over to pull the backpacks up and then climb up yourself. We parked and started at the loop trail and came back out through the Brook trail.

Must love boulders!

We parked at the Brook Trail trailhead parking lot and walked along the road and took the Loop Trail to summit. It’s pretty steep right from the start so you get a good cardio workout in. You quickly start bouldering, which in our opinion is super fun. I’ve seen people take their kids up but I’d encourage you to re-consider if your child is not an experienced hiker. Fat Man’s Misery is certainly a challenge. I’m personally very short and find it difficult to get my leg up to the first big step so I can hoist myself up to reach the iron rungs. There is a perfect little pocket to reach your left hand up towards but you can’t see it at first. I just kind of reached around and when I noticed it, it made things much easier for me. Also, if you have poles attached to your pack be careful not to get stuck once you’re going through. My husbands have gotten him pretty badly wedged up in there and was difficult to figure that out as they were on his back. We have never gone down the Loop and probably never will. It’s do-able for sure but will be a challenge and make for a very slow descent. We really enjoy following the brook down the Brook Trail. The pond at the summit is super pretty and the views are amazing. Happy trails!

Great hike... challenging but rewarding... fat man's misery gave us a run for our money(we had 2 kids with us) but we made it and I'm so glad we did this hike!

Just completed this hike today! Great rewarding views from the top. We had planned on doing an out and back up the Brook Trail but followed some fellow hikers from the parking lot down the road and ended up at the trail head for the Loop Trail instead. Whoops. We decided to go for it anyways.

It’s a steep climb but full of really neat features. We did have our 70 lb. dog with us and when we reached Fat Mans Misery, were in a bit of a pickle. Some very kind hikers helped us get the dog through the chimney and after that it was a pretty easy stretch to the top. We hiked down to the pond and descended Brook Trail to the parking lot. Very glad we did the loop this direction as the rocks were slick on both trails and coming down Loop would have been hard and slow. I definitely wouldn’t recommend Loop Trail if you’re bringing Fido with you, as it was a nerve wracking experience for us. Everyone survived though and all in all it was a rewarding experience!

I would not recommend dogs on the harder route. Sustained scrambling not for paws.

awesome!! Def would not recommend for dogs.

on Tumbledown Mountain Trail

26 days ago

My husband and I went up on the Brook Trail, then on the Pond Link Trail and finally down the Loop Trail. The Brook Trail was very nice going up, not too hard at the beginning and the last 15min ask for more strength but like everybody said, it is more than worth it! Going down though the Loop trail was challenging, yet nice too. I agree that it might be difficult for short people, especially through the rocks with the metal ladder. By doing that loop we needed to walk back to the parking spot and that took us about 25min.

Tumble down pond is a wonder on its own! Makes you appreciate what mother nature is capable of. I did the loop which the rangers consider a very difficult hike and I would have to agree with them, the elevation gain on the hard trail up is no joke. But at least you can go for a swim when you get to the pond! Water is super clean and beautiful and hopefully we can keep it that way! Let me add there is an easier way to reach the pond, basically your decent trail on the loop, so with this easy way up it gets pretty crowded, especially with children, so if possible go off season. Camping is allowed by the pond but if my memory serves me right camp fires are not allowed.

5 months ago

I completed this hike in October. I’ve never seen such a beautiful colors...or stunning views of New England fall foliage before this. The loop is challenging, but rewarding. Do this as an in and out if you want to avoid very steep climbs and a chimney climb. Not for the faint of heart.

My favorite hike in Maine! Good mix of terrain and amazing views!

Such a great hike, the Loop trail is not for those who don't like vertical climbs up rock faces and through chimneys, but I loved it for being fairly new to this kind of hike. It also doesn't seem to be dog friendly-- I'd take the Brook trail if there are children or dogs. I took the Loop trail to the pond, and descended via the Brook trail.

a note on the chimney: packs don't easily fit so it's best to haul that out first.
Also I would rate the loop trail as a moderate hike.

Also the Loop trail isn't well marked, so pay attention for the trail markers, especially near the top.

The Brook trail is much more accessible.

I did this hike in late September. It was beautiful!

still great views at end of leaf season!

Went up the brook trail and it was challenging but such a fun experience. Beautiful at the top so worth it and has a cool little pond up top. Only bad thing was trying to find the parking area/where to begin wasn't very many signs.

Love it! One of my favorite hikes!

We parked at end of Morgan road. The trails are well marked and challenging. The pond is a sweet spot to rest and enjoy lunch before taking the brook trail to Byron road. From there we took the connector trail back to where we started.

loop trail not good for dogs unless you can fit them in your pocketbook, we had my 85 lb pup without some help of 3 young guys we would have had to turn around, we all made it awesome day!

8 months ago

Ascending the loop trail is hard work, but I was expecting it to be longer and harder and was a bit disappointed with the hike part. It took me 20 minutes to walk up the gravel road, 1.5 hours to ascend the Loop Trail, and an easy hour to come down the Brook Trail. The pond is absolutely beautiful and I had a refreshing, long, indulgent swim. Would love to come back for the mountaintop pond! There are maps on either trail head if you need one. The Brook Trail is a steady incline, much more accessible for families. If I were to bring my 12 year old, I'd do the Loop Trail again, but with my 7 year old or my dog, I'd go up the Brook Trail.

Hard! Several places to use upper and lower body strength- rocky steep and through a Little Rock cavern with a sort of ladder .. worth it at the top! Feel very accomplished and there pond is amazing as are the views.
Not for dogs! Not for kids! Not for the outta shapers ... sorry.

this is a hike I've done many times, even spent a few nights at the pond. this is a great place. Is difficult in areas. be prepared and watch your step.

Towards the top there is a "chimney" with ladder rings and nearly impossible for pups unless they are small and you can carry them or you have a couple people to help. I have a 70 lb German Shepard and unfortunately didn't do enough research about the trail itself, so we had to turn around. Next time I'll go up the Brook trail but really enjoyed the hike up to that point!

just plain awesome!

We parked at Brook Trail parking lot, then walked up the road to the Loop Trail to start the hike. The Loop trail up was hard, but efficient. There is a narrow "chimney" near the top which was a bit tight with a backpack. The rocks were a bit slippery throughout even though it hadn't rained in a few days. There were wild blueberries at the top (in August) and the lake was chilly, but not ridiculous. Glad we went down Brook Trail as it was much less slippery/steep.

It was a tough hike but very rewarding! I hiked this going up and took Brook Trail going back! The blazes are harder to find once you are in higher elevation so be careful for I went off the path a couple of times! Definitely worth it!

we hiked the loop up, to the pond, And down brook. about half way up we got caught in a shower, and the rocks were slippery. this is definitely a hard trail! Be prepared to do some scrambling, and really pay attention to the blazes, as it could be easy to get off trail (not well marked when you gain some elevation. don't forget a trail map the loop is not an out and back). The chimney isnt too bad once you figure out how to get in. Overall a really great hike. if you're a casual hiker, consider this a good level or two up.

We did the Brook trail. Very steep and strenuous. Out and back a little over 4 miles. Our group ranged from 7 years old to 57 and we all made it. Lovely lake and views at the top.

10 months ago

Fun mountain to climb! Cool exploring on top. Great loop, gives you 2 different perspectives of the mountain.

One of my favorite hikes in Maine. We usually take the loop trail up and the brook trail down. The only problem is at the end you have to hike back to where you parked. Well worth it though. The views from the top are amazing and the pond is very rewarding after a tough hike

10 months ago

loop is HARD!!! However, so worth it. view is great, trail is a workout, and the pond at the top is refreshing.

Excellent day hike. Be advised though, the loop trail is definitely the harder of the 2 trails to the summit. It's also a little hard to follow so watch the blue blazes and be prepared for some steep rock scrambles and a tight fit through the chimney near the top. We took off our packs to squeeze through. The views from the top are amazing and the little pond up there is simply teaming with fish!

11 months ago

I loved loved loved this mountain. As of right now this is my favorite hike to do alone. I only have been here once but everything about this place is perfect.... except for the trail markers. I felt like I was playing iSpy the whole way up Loop Trail. I managed to get off the trail once and that freaked me out but I am here writing this review so I did make it back to the trail :) Loop Trail is definitely a challenging go but it is very doable. The beginning I was thinking this is kind of a joke in terms of being an advanced trail... but the further and further you get into its not for the faint of heart. I was also hiking at a pretty quick pace.
I didn't have a clue about the chimney so luckily a group wasn't too far behind me to help me out with that. I thought I had done my fair share of research about the mountain before tackling it on my own but oh well.

The summit is gorgeous. Next time I will go up to Little Jackson's summit as well. The pond is beautiful and swimmable. Getting off the mountain I took brook trail. Easy way to get down.

I am a happy girl :) definitely recommend this place to everyone

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