Posted on November 27, 2019 and last updated on November 28, 2019

Messalonskee Stream Trail, Oakland


  • Preserve Size: N/A
  • Trail Mileage: 2.6 miles one way
  • Pets: yes
  • Difficulty: moderate
  • Sights: Messalonskee Stream, ruins of old textile mill

When you’re starting from the southern trailhead, off Kennedy Memorial Drive, the first three-quarters of the Messalonskee Stream Trail is by far the most enjoyable. There is ample parking at the trailhead, and the non-wheelchair accessible trail begins behind a chain link fence. Then the trail proceeds 2.6 miles to Rice Rips Road. But don’t feel pressured to go the whole way! The first 1.7 miles are the best part—scenic, well-marked, and interesting. When you reach the powerlines, turn around and head back the way you came.

Soon after starting off from the Kennedy Memorial Drive trailhead, walkers will see the the ruins of the Cascade Woolen Mill on the opposite side of the stream. The mill, built in 1882, made wool, twilled, and cotton textiles. It operated until 1997. The closed plant burned in 2010.

The path makes its way high up on the rather steep river bank, through an old-growth stand of…Hemlock trees, I think? The forest is beautiful. The trail crosses a couple of streams, passes a picnic table in the woods, and eventually comes out to what I thought was the highlight of the walk: a little peninsula that juts out into the wide Messalonskee (it’s dammed downstream). There is a picnic table here.

The trail continues a short ways from this point until it meets up with the power line corridor, at roughly 1.7 miles. The .9-mile remainder of the trail is slightly less charming as you make your way under the power lines, finally coming to a road road right before the train tracks. Swing left here, and walk down a staircase to the dam. More stairs take you over the large leaky water pipe (technically, a penstock). The path continues alongside the penstock to Rice Rips Road. The small parking area is across the street from the trailhead.

KM Trails says it’s planning to continue the trail here to connect to County Road, and from there Quarry Road and North Street. Lots of good info about local walks here.

Directions: The southern trailhead—the more popular starting spot—is on the right, off Kennedy Memorial Drive, right before the stream crossing. There is room here for about a dozen cars. The northern trailhead is on Rice Rips Road, across the street from the trailhead. The small parking area off Rice Rips Road is big enough for two cars perhaps. You’ll see the “Trail” sign at the gate: Walk around the gate and alongside the black leaking penstock about 1/4 miles toward the dam. Climb the stairs up over the dam and follow the wide dirt path up a gentle incline to the power lines. Turn right onto the power lines and walk to the footpath on your right. The footpath will be marked with a “Trail” sign.


Let me know if you have any trail updates or corrections!