Looking for a great trail near Oakland, Maryland? AllTrails has 5 great hiking trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails around Blackwater Falls State Park or Swallow Falls State Park, we've got you covered. You'll also find some great local park options, like Redwood Regional Park or Lake Chabot Regional Park. Ready for some activity? There are 4 moderate trails in Oakland ranging from 1.6 to 7 miles and from 2,349 to 3,362 feet above sea level. Start checking them out and you'll be out on the trail in no time!

hiking

Oakland, Maryland Map
VIEW FULL MAP
hiking
4 days ago

I have taken this trail 3 times and enjoyed it a lot. This trail has a beautiful view of several falls. It is not difficult - the only significant climbs have steps, so it is good for a mixed group with some inexperienced hikers. NOTE: I would advise caution in below freezing weather as much of the trail will cover over with ice due to the spray and some sections become impassible due to the lack of handrails.

hiking
snow
8 days ago

Beautiful trail with two great waterfalls at either end. Great for all ages being just under a mile for the full loop. We hiked with lots of snow and it was a magnificent site.

hiking
1 month ago

Beautiful Beautiful Place. The power of the water is amazing. Multiple places for nice pictures.

hiking
1 month ago

I’ve never seen the falls with this amount of water! It was a powerful display of nature!

hiking
3 months ago

May be slightly difficult for a beginning. Continuous uphill slope, but it has a nice view at the end with a picnic area. Very rocky (and slippery when wet). Make sure you have good boots!

We just missed the fall colors but it was soon after a rain so the waterfalls were great. My mom is 69 and not in good physical shape but she was able to complete the 0.9 mile hike.

hiking
3 months ago

Short but lovely! Took the family here for a sort hike. It was busy but worth it. The falls were great and running full from all the rain. Definitely worth the stop!

hiking
3 months ago

Completed this trail on 10-22-18, beautiful views up top, some snow on the ground as well. The trail was very muddy especially at the base due to the recent rain and snowmelt. Very nice hike that doesn't take too long to get to the top.

This is a popular trail but it’s worth it!

hiking
4 months ago

Completed this hike over last weekend. Very easy trail and very straightforward. One of the first times I think the trail is too well marked. Parking is possible right across the trailhead. Views at the top were not that great except only in one direction, but the area around summit is very well done. A statue indicating the Maryland/Delaware border can be found on the same trail. The USA’s smallest church can also be found right down the road. Overall was a great leisurely hike but fours stars just because it was quite muddy and nothing really too special unless you’re a Highpointer.

hiking
4 months ago

Quick, continuous uphill slope with beautiful views at the top. There's only a small sign for the trail on a busy road, so there aren't huge crowds, which is always nice.

A great family hiking trail!

I was a little skeptical because it was such a popular trail and I was thinking it.kight be a let down... and I proven wrong. it's a great walk/hike with absolutely gorgeous scenery. you're only hurting yourself of you don't go!

beautiful scenery and sounds

short and steep, perfect for highpointers! probably not worth it if you're not interested in bagging all the high points but still a nice little hike.

Great hike on a short loop. I went right first to Tolliver falls which is small but has a little beach and pool area if u want to cool off. Then upper falls that you can go on and has a nice vista view down river and a little down the river a nice view back upstream at it. Lower falls after that then nice rocky hike to muddy creek falls the biggest of the group.

hiking
6 months ago

Short, steep trail with nice views on top. Very little traffic on the trail today considering it leads directly to a state high point (MD in this case). Very well signed and blazed. Only drawback is that the trail is rather rocky. Be sure to wear a good pair of boots.

hiking
6 months ago

Awesome trail. One of, if not the most beautiful trails we’ve hike on the east coast. And we’ve hiked a lot. Similar to Otter Creek, but not as remote. We only passed two or three small groups. Lots of water crossings, but that was fun. We’re glad the trail isn’t more “domesticated.” Better maintained. As it is It gave us much more of a true nature experience. We saw a mother bear and her cub. We saluted and kept going. Fast.

We had allotted 4 hours and due to all the stream crossings we were behind by about 45 minutes so we decided to hike to the end on the trail and then back to parking via the gravel road. The long uphill hike took about 1-1/2 hours. We arrived precisely 4 hours after our start. If you can’t do the whole trail, at least drive down the road to near the end to some pullouts. The most awesome falls are down there. Loved it and we’ll return.

on Swallow Falls Trail

hiking
6 months ago

I considered this more of a walk than a hike. The falls are pretty. You can connect with other trails to see a total of three waterfalls.

on Lostland Run Trail

hiking
6 months ago

Great trail! Two waterfalls, two suspension bridges and lots of stream crossings. You will get wet.

hiking
6 months ago

Picturesque, accessible to everyone, and a pretty reasonable hike.

Wow. This trail could be something really special. First, it is easy to access. And, it follows a stream, so the elevation changes are minimal. It’s mostly treed, too, which is perfect in the summer.

What’s missing, you ask? Oh my gosh. Bridges. There are so many stream crossings. A few have good bridges or wooden planks. The rest, you are on your own trying to step onto slippery wood or rocks. We had to make our own bridge from a fallen tree on one crossing. Another we had to take our boots off to cross. This state park could do a lot better trail maintenance. My husband and I are young and in shape, but we agreed that several people probably get hurt at crossings each year.

I would recommend this hike in the late summer or fall when the water levels are lower. Or hiking in your water shoes!!

hiking
7 months ago

There is a longer trail this is apart of that you get to see three different and beautiful waterfalls! Very accessible to all! The park does cost an entrance fee per person. The trails and waterfalls were packed. Many people were swimming at the waterfalls. The rocks are very slippery be cute to wear shoes with traction. The trails are also not very well marked. Be prepared to feel lost. But once you get to the falls it will all be worth it.

hiking
8 months ago

beautiful scenery

nature trips
8 months ago

Impressive falls. Sometimes the falls trails are a let down, but this one is legit. We were here in June and you could walk right out onto the drop.

hiking
8 months ago

When in the Deep Creek Recreation Area you need to walk this short trail in Swallow Falls State Park. There is paved parking at the trailhead and overflow parking around the bend. The trailhead is under an arch that says Swallow Falls Canyon Trail. A very short spur takes you back to the main loop where a sign points left for Muddy Creek Falls and right for Swallow Falls. It takes about 15-20 minutes to reach the falls in either direction. The western side of the loop is smooth clay with pea gravel and the east side hugs the Youghiogheny River and is a mild rock scramble. Creeking shoes, sandals, or sneakers are best - boots and trekking poles are unnecessary. Along the river there are several short trails down to the water and most provide great photo opportunities. Fortunately, all of the paths are easy to climb up and down with good places to step. Both waterfalls are very easily accessed, that is, you can walk right up to the falls although signs advise caution. Muddy Creek waterfall is very handicapped-accessible with van parking and a long wooden ramp leading to a wooden observation deck.

hiking
8 months ago

This trail is breathtakingly beautiful. We hiked with my dad and 6 yo son and we actually went off track a lot and it was amazing. We crossed many rocks/water area. It is short enough to get around the whole hike in 3.5 hours.

Great trail!! It snowed the day we went and the fresh snow made the trail look beautiful! Definitely going back to see it when everything is green!

hiking
10 months ago

Loved this trail. Just hiked this last weekend for my first high point hike. Trail was well marked on trees. Beautiful view at the top with a registry which I loved. The trail is still pretty wet from the snow. Little Rocky on the first part of the trail.

Load More