New York City, NY: Alander Mountain

Tag three mountains, including the highest point in Connecticut, on this 12.1-mile hike in Mt. Washington State Forest. Attractions include: pretty streamside camping, spectacular ridgeline hiking, fine mountain views, and a bounty of blueberries.

Heading out the door? Read this article on the new Outside+ app available now on iOS devices for members! Download the app.

Caution: Keep an eye out for rattlesnakes.

Trail Facts

  • Distance: 19.6



Location: 42.0863990783691, -73.4620666503906

Trailhead: Register if you’re overnighting and pick up free trail map. Head straight across the meadow on the Alander Mountain Trail. Look for Hunts Pond on the L.


Location: 42.0868949890137, -73.4682006835938

After a short section in the woods, you’ll suddenly emerge to an open area with views of Alander Mountain ahead. In summer, veer R off the trail about 50 feet and scan the ground for low-bush blueberries. They’re tiny but succulent; fill a bag to snack on or to mix into tomorrow’s pancakes or oatmeal.


Location: 42.086296081543, -73.4702835083008

Cross Lee Pond Brook on small footbridge. Like Ashley Hill Brook, which you’ll cross next, this stream eventually flows over Bash Bish Falls.


Location: 42.0864448547363, -73.4715728759766

Stay R at 3-way with the Charcoal Pit Trail, which is an optional shortcut on the return. This part of the trail follows an old road bed; you’ll occasionally notice rotting road timbers poking up out of the dirt. On the R, note one of New England’s ubiquitous stone fences–this is a good place for reading Robert Frost at night.


Location: 42.0879516601562, -73.4738388061524

Veer R @ 3-way, staying on the Alander Mountain Trail. To the L is the Ashley Hill Trail, on which you’ll return. You could reverse the direction, but I think it’s more pleasant to get the big climb up Alander out of the way, then enjoy the long, shady downhill along Ashley Hill Brook and its wide, smooth trail.


Location: 42.0882186889648, -73.4749526977539

Cross Ashley Hill Brook on a small footbridge. This is a good place to tank up on water and take a pleasant breather before the 1-plus hour climb to Alander. You can also hiking quite a ways downstream, passing several excellent swimming holes (only waist-deep) and picnic spots along the way.


Location: 42.0922241210938, -73.4859313964844

Side trail to campsites. In the middle of a long uphill section, a blue-blazed path leads left about .5 mile to decent but not spectacular campsites. Camping is officially permitted only at two designated areas, this one and a nicer location along Ashley Hill Trail (which was closed in August 2005–call the ranger for an update).


Location: 42.0924644470215, -73.4945068359375

Cross seasonal stream that’s often dry in summer. Look around and enjoy some of the most bucolic mature forest in the Berkshires.


Location: 42.0909461975098, -73.4968566894531

Good rest stop before continuing onto a steeper section of the climb to Alander. Stay R, following the blue blazes into a switchback.


Location: 42.0913391113281, -73.4992218017578

Sometimes there’s water here, at a flat, righthand bend in the trail. Go L about 15 feet on a game trail to a small, spring-fed trickle.


Location: 42.091236114502, -73.5006256103516

Another seasonal water source.


Location: 42.0881462097168, -73.5032577514648

Skanky old cabin that gets more tenants than it’s dank, dark, musty interior deserves. Camp here only in an emergency.


Location: 42.0877723693848, -73.5035095214844

Turn R at the T just 50 feet beyond the cabin at a sign that says “To Taconic Trail”; head uphill.


Location: 42.088191986084, -73.5039520263672

Turn L @ 3-way, and follow the white blazes to Alander’s summit. Turning R here leads to Bash Bish Falls on a long, rugged, often steep downhill hike.


Location: 42.0870513916016, -73.5052719116211

Summit of Alander Mountain. To the W are views of the Catskills High Peaks and the farms of Dutchess County. To the S, you can see the ridge that leads to Brace Mountain, the highest peak in that direction (bald on top), and Mt. Frissell (just to the L of Brace). You’re now on the Taconic Trail, which runs from south of Brace all the way north to the Catamount Ski Area in Massaschusetts (see photo of trail sign). It’s often windy up here, and sometimes crowded, so save your lunch for later in the hike, when the views get better and the crowds thin. But do spend a few minutes gathering blueberries, which grow all over the summit. Note: Make sure you avoid the other, blackish berries growing up here, which can be confused with the similarly sized blueberries (see photos for comparison). From here, return to WPT 13 to get on the Alander Loop Trail, which will reconnect with the Taconic Trail later; this diversion keeps you up on the ridge rather than dipping way down on the Taconic Trail, only to climb back up.


Location: 42.0873908996582, -73.5020599365234

View back to Alander and more blueberries.


Location: 42.0832176208496, -73.4999923706055

This section of trail is tight, almost tunnel-like, due to overgrown scrub oak and rhododendron. You may want gaiters and long sleeves here to avoid the scratching. Farther ahead, a trail crew has recently done excellent work to cut back the shrubs.


Location: 42.0819892883301, -73.5006408691406

Turn R @ confusing 3-way; follow blue blazes downhill. Just below here, I saw an odd half-green, half-brown frog.


Location: 42.0790328979492, -73.5050277709961

Turn L @ 3-way intersection back onto the Taconic Trail (white blazes). A small, hand-carved sign says “Gentz’s Corner.” Ahead, you’ll briefly cross into New York as the trail winds through beautiful open forest and gradually climbs back towards the ridge on old carriage road.


Location: 42.0769805908203, -73.5049285888672

Fairly reliable water source, the first in several miles.


Location: 42.0724258422852, -73.5040740966797

Straight at 3-way with red-blazed Robert Brook Trail, which leads down to a parking lot on the New York side.


Location: 42.0712013244629, -73.501594543457

Photo of a grassy roadbed winding through mature beech, birch, and maple forest. There’s little understory, mostly ferns, so the sight lines are great and the breeze is unimpeded. These roads are one of the things I love about New England, because there a sign that nature can reclaim a great degree of wilderness feeling, even after being logged or farmed. No doubt this area was heavily used a century ago, but now the only signs of that exploitation are a few stone walls and hiker-friendly roadbeds like this.


Location: 42.0700263977051, -73.4993667602539

Usually there’s good water on the R.


Location: 42.0582542419434, -73.49658203125

Straight at 3-way; L is a shortcut to the Ashley Hill Trail, a good option if there’s any sign of thunderstorm approaching the ridge.


Location: 42.0483627319336, -73.4941558837891

Bear R @ 4-way at trail sign pointing (the other way) to Mt. Frissell. You’ll return to this junction after summitting Brace Mountain.


Location: 42.0443649291992, -73.4925918579102

Summit of Brace Mountain. Enjoy wraparound views of the gently-rounded peaks and ridges in the southern Berkshires, plus the Catskills and the pastoral landscape in the valley to the W. Frissell is the nearest “high” peak; Bear Mountain, the highest peak entirely in Connecticut, is just to the right and behind it. On Brace, someone has planted a windsock in the summit cairn; it almost always is straight out, thanks to the thermals that blow up the ridge from the west. Continue to South Brace, or retrace your steps to WPT 26 to continue the red-blazed loop.


Location: 42.0490951538086, -73.4893569946289

Straight @ unsigned 4-way; to the left is the Ashley Hill Trail. You’ll return here after tagging Frissell.


Location: 42.0495414733887, -73.4874649047852

Tri-state marker dated 1898. From here, you climb rather steeply to Frissell.


Location: 42.0495452880859, -73.4837875366211

Holy *&^*%&^!!!!! I nearly stepped on the biggest rattlesnake I’ve ever seen, and the first I’ve seen in this area. I was chugging up the trail, which alternates between forest and open slabs of rock here, when I heard a sudden unmistakable rattle and looked up to see this beautiful but monstrous snake only two strides in front of me. It was easily four feet long and as thick around as my wrist or lower forearm, and it had a bright yellow belly, somewhat small head, and 7-section rattle. No doubt it was sunning itself on the rock when I came along. Fortunately, it seemed very sluggish, because it didn’t give me more than that first rattle as it slithered slowly off the trail into the bushes. I waited a couple minutes before going by, really nervous that it would strike, or that its mate was nearby. Phew, neither happened, and I continued to Frissell-only to see the same snake in the same place only 10 minutes later on the way down! Ack, my heart was beating like crazy.


Location: 42.049690246582, -73.4828491210938

Highest point in Connecticut. This anticlimactic location is marked by a pile of rocks and a small metal benchmark. Perhaps that’s appropriate, since the highest point in Connecticut is actually on the shoulder of a mountain (Frissell) whose peak is in Massachusetts. The highest peak that’s entirely in Connecticut is Bear Mountain, which is visible through the trees about 5 trail miles away to the SW.


Location: 42.0494232177734, -73.4880447387695

Another rattler! Once again, despite my nerves being on edge and my eyes intently focused on the trail, I nearly stepped on it. That’s because it looked just like a stick laying next to the trail–until I got close enough to see its tongue flicker. This guy was a bit smaller, but more sinister looking, and he immediately got defensive, coiling up into a ball in the middle of the trail and giving me a good, long rattle and hiss. I waited 5 minutes, but he wouldn’t move, so I bushwhacked around, worried the whole time that he must have a nest of babies somewhere nearby. Needless to say, my heart was racing and I spent the rest of the day thinking every noise–and every stick that popped up and nicked my leg–was a rattlesnake coming to get me. Irrational, I know, but there’s nothing quite like that rattling sound suddenly coming from your feet to change your entire perspective. Return to WPT 28 and turn R onto Ashley Hill Trail, beginning long descent to WPT 5.


Location: 42.0611114501953, -73.4870529174805

Possible water source. Often dry in late summer.


Location: 42.0683097839356, -73.4892730712891

Veer R @ 3-way, continue following blue blazes. Trail follows graded roadbed.


Location: 42.071117401123, -73.4894256591797

First spot with guaranteed water since before you began climbing Alander. A few feet to the L is Ashley Hill Brook.


Location: 42.0782470703125, -73.4809417724609

Stay straight at 3-way with Charcoal Pit Trail. (Option: Go R here and save a bit of mileage while climbing up and down on a more rugged path.)


Location: 42.0829429626465, -73.4824905395508

Bear R @ Y next to outhouse. The trail to the L leads down to very nice official campsites next to Ashley Hill Brook (currently closed: August 2005), plus swimming holes and big sunning rocks. Continue to WPT 5 and turn R to return to your car.


Location: 42.0505867004394, -73.4947280883789

Veer R @ Y and follow the white blazes onto open slabs of granite with primo views and rest spots in about 50 feet. Lots of blueberries here, but keep an eye out for rattlesnakes, especially mid-morning and later, when they come out to bake in the sun. This area is known as a prime breeding ground, and a ranger once told a friend of mine that the largest eastern timber rattler on record was found here. That said, I hiked here probably 20 times over 10 years without ever seeing a snake–until this trip (keep going!).

Location: 42.086856842041, -73.4681091308594

Blueberries in hand. ©Jon Dorn

Location: 42.0864524841309, -73.4703903198242

Alander Mountain Trail sign. © Jon Dorn

Location: 42.0880661010742, -73.473876953125

Trail signs. © Jon Dorn

Location: 42.0884666442871, -73.5031433105469

Old cabin. © Jon Dorn

Location: 42.0890045166016, -73.50341796875

Camp here only in emergency. © Jon Dorn

Location: 42.0884666442871, -73.503547668457

Trail sign. © Jon Dorn

Location: 42.0871238708496, -73.5054321289062

Wrong berries. © Jon Dorn

Location: 42.0872573852539, -73.5058288574219

Trail on top. © Jon Dorn

Location: 42.0871238708496, -73.5058288574219

View of Brace and Frissell. © Jon Dorn

Location: 42.0873947143555, -73.5058288574219

Catskills High Peaks. © Jon Dorn

Location: 42.0872573852539, -73.5055618286133

Trail sign. © Jon Dorn

Location: 42.0875282287598, -73.5056991577148

Summit cairn. © Jon Dorn

Location: 42.0875282287598, -73.5058288574219

Good berries. © Jon Dorn

Location: 42.0861854553223, -73.5018005371094

View back of Alander and more blueberries. © Jon Dorn

Location: 42.0832481384277, -73.4999542236328

Overgrown trail. © Jon Dorn

Location: 42.0832481384277, -73.5001373291016

Follow blue blazes. © Jon Dorn

Location: 42.0820693969727, -73.5014877319336

Odd-colored frog discovered on trail. © Jon Dorn

Location: 42.0713996887207, -73.5016708374024

Grassy road. © Jon Dorn

Location: 42.0507850646973, -73.4949798583984

Wide, open rock. © Jon Dorn

Location: 42.0509643554688, -73.4952545166016

Alander sits in the horizon. © Jon Dorn

Location: 42.0443649291992, -73.4925384521484

Trail leading to summit.© Jon Dorn

Location: 42.0444526672363, -73.4925384521484

Summit cairn with windsock. © Jon Dorn

Location: 42.0442733764648, -73.4925384521484

Cairn with Frissell to R. © Jon Dorn

Location: 42.0447235107422, -73.4925384521484

View back to Alander. © Jon Dorn

Location: 42.0445442199707, -73.4927215576172

Me on Brace Mountain. © Jon Dorn

Location: 42.0484313964844, -73.4941635131836

Trail signs. © Jon Dorn

Location: 42.0485229492188, -73.4943466186524

Trail signs. © Jon Dorn

Location: 42.0496101379394, -73.4873809814453

Stone marker. © Jon Dorn

Location: 42.0497894287109, -73.4874725341797

Close up. © Jon Dorn

Location: 42.0498809814453, -73.4824981689453

Marker from 1906. © Jon Dorn

Location: 42.0502395629883, -73.4824142456055

Huge cairn. © Jon Dorn

Location: 42.0496101379394, -73.4843063354492

Snake! © Jon Dorn

Location: 42.0495185852051, -73.4886474609375

Black snake. © Jon Dorn

Location: 42.0494270324707, -73.4881057739258

Snake slithers by the log. © Jon Dorn

Location: 42.0496978759766, -73.4881057739258

It’s a big rattler! © Jon Dorn