There are two trailheads to Sawyer Mountain Highlands: the Limington side which is a 3.6 mile round trip hike to the summit and back, or the Limerick side which is 2.4 miles. We opted for the latter; I'm not sure we really missed anything by not exploring the Limington side of things, truth be told, so don't worry too much about which you go with.
Smith Trail picks up right in the parking lot on the Limerick side; the entire trail is extremely well marked with wooden plaques painted red and stamped with a yellow turtle, and brightly painted arrows when you need to take sharp turns. The combo of those two colors really pop regardless of season, so you should have no problem staying the course (there's also plenty of directional signs at intersections pointing which way is what and the distance to it). The first bit of Smith Trail is relatively steep so be sure to have good shoes, a walking stick, and knowledge that it's a serious work-out. We saw plenty of people turn back because they wanted a flat, easy walk in nature and not a hike. You don't need gear, but if you come in flip-flops and expect to not sweat then you've done yourself a disservice. That being said - it's always nice to be rewarded after putting in the effort... and Sawyer Mountain Highlands does NOT offer that. The view at the summit is underwhelming as its primarily obstructed by evergreens. Sure there are some spots through the trees you can see glimpses of across the valley below and mountains beyond, but mostly you're just really high up looking at nearby trees. We thought comparable hikes with far better summit views included Douglas Mountain in Sebago or Pleasant Mountain in Bridgton. The coolest bit of this particular summit is the sign marking where a whale oil light was used to navigate ships in Portland harbor ('cause you can see Sawyer from the ocean apparently).
Leaving the summit, you can go back the way you came (Smith Trail) or you can opt to take the old Sawyer Mountain Road - personally, while I don't like doubling back and seeing the same things on my hikes, I regret taking Sawyer Mountain Road back to the parking lot - not sure if it was a former riverbed, but the entire thing was rocky and pebbly (goodbye articular cartilage around my patella, I'm sure I didn't need you). It also came out near someone's house at the end of Sawyer Mountain Road where large, growling, bark-screaming German shepherds at the edge of their chain were snapping at us (and hung on trees and fences there were loads of "stay out"/"private property" signs hung everywhere). Just a heads-up.
All in all? I'd prefer to go to Libby & Son's nearby, eat a truckload of donuts, and walk their beautiful grounds which actually offers far more expansive, impressive views. read more