Looking for the best trails around Oakland?

Explore the best rated trails in Oakland, ME, whether you're looking for an easy walking trail or a bike trail like the Whistle Stop Rail-Trail and Four Seasons Adventure Trail . With more than 16 trails covering 89 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Recent Trail Reviews

Bucksport Waterfront Walkway

bucksport water front

April, 2024 by cromeenesa

I love the waterfront it’s such a beautiful area and the scenery along waterfront is awesome

Kennebec Valley Trail

This is not a bike trail, this is a atv trail, the people drive the side by sides like they are out of cigarettes on the trails up here.

January, 2024 by craigerskine

This is not a bike trail, this is a atv trail, the people drive the side by sides like they are out of cigarettes on the trails up here.

Four Seasons Adventure Trail

Beautiful Ride

October, 2023 by debbiepch

Lots of bright yellow and gold foliage today on a wide flat trail. Some areas had washouts that were clearly marked. Overall it was a fantastic ride.

Accordion

Four Seasons Adventure Trail

Scenic ride

September, 2023 by joann.nelson76

Scenic ride

Kennebec River Rail Trail

Was a wonderful morning for a bike ride,

September, 2023 by justadditup

Was a wonderful morning for a bike ride,

Whistle Stop Rail-Trail

Beware!

August, 2023 by backyard37_tl

We started in Livermore Falls and loved it! However, about 6 miles north, the trail is washed out and collapsed into a ravine. We tried to go around out on Main Street and up Macomber, but Macomber St was also washed out about 1/2 way up the hill and the road was closed. Will have to go South from Farmington next time!

Four Seasons Adventure Trail

fun!

July, 2023 by w5y6t2jgvb

Rode this on a Friday with our gravel bikes; very few people; well-maintained with plenty of room for the ATVs we met to pass.

Papermill Trail

Atvs

June, 2023 by mywhitetiger4

I love walking on the trails, I started walking there a year ago, its helped me to build my strength and lungs from struggling with long covid, its quiet and peaceful, but I'm afraid the allowing of atvs is going to ruin that, ill see how it goes but if the atvs ruin the peaceful surroundings ill be looking for another peaceful place.

Norway Branch Rail Trail

Walked this trail for many years and they have fix it up nice

May, 2023 by joebeehut24

Walked this trail for many years and they have fix it up nice

Belfast Rail Trail on the Passagassawaukeag

easy, pleasant walk

October, 2022 by tinsleym

Lovely, flat, well kept. I started a bit further back at the Belfast Boathouse, walked all the way out and back for almost 6 miles.

Penobscot River Walkway

Has a nice River view, can occasionally hear trains tooting, people are dining to the side on restaurant patios

August, 2022 by rosalievalerio63

Has a nice River view, can occasionally hear trains tooting, people are dining to the side on restaurant patios

Penobscot River Walkway

Nice River view, can occasionally hear trains tooting, restaurants with people dining can be seen to the side, fine for a City Walk

August, 2022 by rosalievalerio63

Nice River view, can occasionally hear trains tooting, restaurants with people dining can be seen to the side, fine for a City Walk

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