Highlands Ridge Trails, Bridgton



I mapped more than 9 miles of trails here at this vast Nordic ski trail system, which wraps around the Bridgton Highlands country club. And my map doesn’t even show the full extent of trails. North of my map, there are even more trails—with more to come, possibly, in the future! The trails on the actual golf course were closed when I visited. The groomed tracks in the surrounding forest are protected, shaded, and pretty. A couple additional short trails in the woods were closed for logging.

The most impressive part of this spot is that the whole system is maintained by volunteers, with “well-worn machines and homemade drags.” Donations are appreciated. Because the trails are in the valley, protected from the sun, you can ski pretty late into spring. When we visited in early March of 2019, after a not-great winter for skiing, there were still pretty decent groomed tracks (for Classic skiing, only). The trails are mostly well-marked, with maps at most intersections. Paper maps are available, too, at trailheads.

For the most part, the trails are easy, but there are some long, gradual hills. In general, you’re going to be headed downhill heading northeast (away from the country club and toward Middle Ridge Road).

Directions: The trailhead is off the access road to the Bridgton Highlands Country Club, which is off Highlands Ridge Road. You will find one of the main trailheads next to the tennis courts.




Stevens Brook Trail, Bridgton

Do not try this walk without a map if you are going out for your first time! It is a little tricky following the trail. In fact it feels a bit like a treasure hunt, with you following clues and barely discernible signs to go the right way. 

If you do manage to successfully get from one end to the other — a 2.5-mile stroll from Long Lake to Highland Lake, or vice versa — you will enjoy yourself and follow a pretty stream. This is a wonderful way to lace a public trail through a town.

Here are my directions to navigate this trial, which really could use a few more signs. I started on Long Lake. This end of the trail begins behind the power station on Powerhouse Road. If you’re facing the station, the trail is slightly to your left. It passes by some deepish pools in the brook and emerges onto Kansas Road, where it makes a slight detour on the left to look at what I think must be an old dam? Then you continue on Kansas Road, taking a left onto Smith Ave., where you pick up the trail again on the right. Bear to the left when the trail diverges, and you will cross a small meadow and emerge onto Route 302, next to a gas station. Go right, then take a left onto Main Street, and then a quick left on Depot Street. You pick up the trail again behind a blue building that held, in Oct. 2016, a florist shop. When you emerge again onto Depot Street, take a left and look for the trail on your left. Eventually, the trail becomes a boardwalk, passes under a footbridge, and comes out next to the movie house. You cross Main Street again, staying left of the building and to the right of the brook. You walk along a raised berm here until you come out onto the road. Turn left onto Bacon Street, and then turn right after 50 feet or so onto the path, which crosses a little field to the footbridge. You can cross the footbridge here or walk next to the red house (where you have a right of way, I believe) to reach Highland Lake park.

Directions:  To get to Highland lake park and beach, take Main Street through town. If you’re coming from the east, follow the curve of the road, and then take a right onto Highland Road. If you’re coming from the west, the park is to your left before you enter down town. From Highland Road, there is a large parking area on the right, and the path starts to the right of the red house at the far end of the lot. You can also pick up the trail from the small pedestrian bridge the connects Shorey Park.




Pleasant Mountain, Denmark and Bridgton

I think this might be Maine’s most popular mountain, this one or Tumbledown. The 2,006-foot Pleasant Mountain (the highest peak in southern Maine) is just an hour drive from Portland, and it has beautiful views, so it’s common to encounter many hikers at the summit on a nice day. That being said, there are several routes up and down this mountain — some, I believe, more popular than others.

Loon Echo Land Trust has done a great job with this ~10.3-mile trail system. Their map has good info about trail distances and elevation gain.

The classic way up Pleasant Mountain is the 1.3-mile Ledges Trail, a short, somewhat steep and glorious trail to the main summit, with ledges and views along the way. I always find most hikers on this path. A less popular trail (at least, based on observation!) is the 2.9-mile Southwest Ridge Trail, which in my mind is just as beautiful as the Ledges Trail, a bit less steep and a little longer.

Over on the north side of the mountain, you have the option of hiking up the rather steep 1-mile Bald Peak Trail, and across the gentle 1.2-mile ridge to the main summit. There are stunning views — and picnic tables — at the ski lift and tower, which you can reach if you head off on Sue’s Way Trail from the Bald Peak Trail. I recommend doing this. (By the way, The Needle’s Eye, off of the Bald Peak Trail, is a rock formation that might have water coursing through it when we’re not in the middle of a drought! It’s accessed by a spur off the main trail.)

The Fire Warden’s trail, while nice, is the least exciting way to get up the mountain. If you are able to do a traverse, I recommend going up Bald Peak Trail — and not missing the tower — and over to the main summit, and then taking Southwest Ridge Trail down.

Directions: From Portland, follow Rte. 302 west to Bridgton and continue on Rte. 302 for roughly 5 miles. Turn left onto Mountain Rd. and drive past Shawnee Peak Ski Area. The parking area for Bald Peak Trail is 1 mile down on the right. The Ledges Trail parking area (on the left, the trail is on the right) is 3 miles down.

The Fire Warden’s and Southwest Ridge Trails are on the west side of the mountain, located off of Wilton Warren Rd. and Denmark Rd. Neither of them have obvious kiosks that you can see from the road. To find the Fire Warden’s trail, look for a big yellow mansion on Wilton Warren Rd. The trailhead is just next to it, through a closed gate. You’ll see a warn wooden sign for the trail, and the kiosk is up the trail a bit in the woods. The Southwest Ridge Trail is also not marked, but you’ll see a kiosk if you pull into the parking area.

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Holt Pond Preserve, Bridgton and Naples


Bald Pate trails in blue; Five Fields Farm X-C trails in green; Holt Pond trails in red

My biggest piece of advice for this walk is do not try to access the trail head via the west along Grist Mill Road. The going is very rough on a little car. Instead, get to the parking lot via Perley Road from Route 302. My second bit of advice is to wear good shoes because the going can be wet here, even though there are a lot of planks and boards laid out on the trail.

The roughly 4.5-mile main trail takes you around Holt Pond — although there are a couple other trails to explore here. I at one point wandered off the path…keep to the blazes! I also couldn’t find the connector trail to Town Farm Brook Trail, although you should, theoretically, be able to walk from Bald Pate Mountain to Holt Pond preserve along the Town Farm Brook Trail.

You can also head off the loop trail to a rougher trail that crosses Grist Mill Road and climbs up Byron’s Hill (no views, at least not in summer). The trails here don’t get much foot traffic — they’re pretty overgrown. I followed a blazed trail that branched off right from the Byron Hill trail for a ways but eventually lost it. It likely continues climbing a nearby hill.

Finally, it is easy to miss the trail when you are walking on the brief stretch of road (Chaplain Mill Road). The narrow, hard-to-see trail crosses a meadow. You’ll probably only notice it if you first spot the trail sign at the forest edge across the field. The more than 400 acres at Holt Pond Preserve are protected by the Lakes Environmental Association. No dogs allowed here.

Here is an interpretive guide.

Directions: From Route 302, turn onto Perley Road. After 1.5 miles, turn right onto the dirt road of Grist Mill Road. Go straight for .3 miles and turn left into parking area, which has a small sign.




Bald Pate Mountain Preserve and Five Fields Farm, Bridgton


Bald Pate trails in blue; Five Fields Farm X-C trails in green; Holt Pond trails in red

This 486-acre preserve, protected by the Loon Echo Land Trust, offers a quick and easy climb to a beautiful open summit with an ancient pitch pine forest and lovely views all around. The easiest way to summit, and the path with the most views along the way, is the .8 mile Bob Chase Trail. The South Face Loop is a bit tougher and longer. You can also walk from this preserve to the Holt Pond Preserve or close to it via the Town Farm Brook Trail (which is blazed with purple tags. I haven’t done this yet and am not sure what condition the trail is in). Cross-country ski trails from Five Fields Farm (in green) also intersect the mountain trail network.

Five Fields Farm grooms their trails in the winter, but call ahead before you head out to check on this (when I visited in late December, they hadn’t gotten around to it yet). The trails are pretty, weaving through the apple orchards and forests. They are also on a fairly significant slop, so expect long up- and downhills. The farm rents snowshoes and skis. (When I returned later in the winter, the trails were groomed and beautiful!)

Directions: From US Route 302 in Bridgton, follow ME Route 117 south. In 1 mile, turn left onto ME Route 107 heading south and drive approximately 4 miles. The Bald Pate Mountain main parking area is located at the crest of the hill, on the left side of the road, just past Five Fields Farm apple orchard and cross country ski area. A short driveway leads to a big parking lot and the kiosk.

Photos below are of the farm’s x-c trails




Pondicherry Park, Bridgton

Pondicherry Park is a 66-acre preserve that can be accessed right off of Main Street in the delightful town of Bridgton. The trail network adds up to about 3.4 miles. There is also a beautiful covered bridge here and a spring that was once believed to have medicinal powers. You can connect to the Stevens Brook Trail here, too. Loon Echo Land Trust holds the easement for the land. 

No dogs allowed except on the designated trail.

In addition, there is a loop designed to please children around LEA’s Maine Lake Science Center, off of Willett Road. If you park at the small lot here and walk a short distance up the center’s driveway, you’ll see the Pinehaven Trail crossing, on your left and right. The center has created fun obstacle courses for children in the woods. And there is a long boardwalk that connects this loop to the rest of the park’s paths. 

Directions: The main trailhead can be found at the parking lot behind the Magic Lantern movie theater and Bridgton Community Center. From U.S. Route 302/Main Street in downtown Bridtgon, turn onto Depot Street.

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