- Winslow Community Trails — Wide, easy, wheelchair-accessible trails.
- Head of Falls — An interesting, charmig city park, with sculptures, a gazebo, amphitheater, views of riverside mills, and information panels explaining the area’s history. You can cross the pedestrian bridge or wander along a track leading north.
- Oxbow Nature Preserve — A small park with views of Messalonskee Stream. A bit rough.
- Thomas College — A highlight of this three-mile trail system is a bench inscribed with “serenity” overlooking a fabulous view of the river. Elsewhere you can walk along paths on banks high above the river, through woods, and around little meadows.
- Merritt Nature Trail — This short trail has a lot of promise, as it borders the Messalonskee Stream, but it needed some attention in the winter of 2018.
- Quarry Trails — This 200-plus acres of city-owned land is a wonderful resource for locals. It has several miles of trails groomed for skiing in the winter; I think it’s a popular place for bikers, walkers, and runners in the non-snowy months.
- North Street Recreation Area/Community Trail — A 0.6-mile wheelchair accessible trail lets you stroll along the pretty Messalonskee Stream in the dappled shade of trees.
- Inland Woods, Pine Ridge Trails — At this large trail system popular with fat bikers, you can make small or medium-sized loops through the woods, up to the ridge and down it again, on trails that connect the hospital with the dog park/Rummels Field.
- Colby College — The 714-acre college property includes miles of blazed footpaths along streams and through forests, as well as wide running/Nordic paths through woods and a beautiful meadow on Runnals Hill. The campus proper is cross-crossed with paved, wheelchair accessible paths and sidewalks.
- South End Leeman Island Trail — A short, easy trail loops through a silver maple floodplain next to the Kennebec River, an enchanting area. The city has had a no-encampment rule here, and the land gets very wet and likely impassable in the springtime.