By Dave Ackerson
Photo above by Meggie Baker

I have been exploring the area since 2001 and have section-hiked the entire Appalachian Trail—I enjoyed the Berkshires section so much, I hiked it a second time. As the assistant director of the Williams Outing Club, I took students hiking, cross-country skiing, and snowshoeing, giving them knowledge of the area and the skills to enjoy the Berkshires on their own—and I am sharing some of that information here. Once you’ve sampled some of the best of the Berkshire hiking areas, you’re ready to explore on your own. Don’t forget water, snacks, and other safety essentials and be sure to slow down and enjoy yourself … unless you’re trying for a fastest-known-time record, in which case, go for it!

Hoosac Range Trail
North Adams
EASY TO MODERATE, 1.6–6 MILES
To get there: Head east and uphill from North Adams on Rt. 2. At the top of the hill there is a large parking area on the right at the overhead “Steep Hill” sign.
This hike is on the Berkshire Natural Resources Council (BNRC) Hoosac Range Reserve and has many interesting features such as great vistas, the Yoda tree, and multiple small cliffs. The trail leaves from the kiosk by the parking area and heads uphill. At the intersection, turn left and continue up to an overlook to the west and north at Sunset Rock. Leaving Sunset Rock you will encounter an intersection in a short distance. Hiking forward and downhill will return you to the first intersection where you can turn left and hike past the Yoda Tree—which resembles its namesake—to the parking area, doing an easy 1.6-mile loop. For a more strenuous 6-mile hike, turn left at the intersection just after Sunset Rock. The trail meanders along the ridge in a southerly direction past many small cliffs before a short trail on the left leads to an easterly vista. Continuing on the main trail, there is a westerly overlook on a short trail to the right. Following the trail 2.1 miles past Sunset Rock brings you to a short trail on the right which climbs to Spruce Hill and a stunning view from the southeast to the northwest, with Mt. Greylock right in the middle. Retrace your steps to the intersection near Sunset Rock, turn left and follow the trail back to your vehicle. Don’t miss Yoda! North Pond is a short distance away if you would like a swim after your hike.

Prospect Overlook Hike
Williamstown
EASY, 1.3 MILES
Getting there: Follow Notch Road from Rt. 2 in North Adams up to the Wilbur’s Clearing parking lot on the left.
This hike is on the Mt. Greylock Reservation, where one could spend many hours hiking. From the parking lot, cross the road and follow a shortcut trail that will soon intersect with the Appalachian Trail (AT). Turn left on the AT and pass through the Mt. Greylock Old Growth Spruce National Natural Landmark—the only old growth red spruces in southern New England. Continue on the AT past the Money Brook Trail to an intersection with the Mt. Prospect Trail on the left. This is a fine view, with Williamstown laid out in the valley below and the Taconic Range forming an impressive backdrop. After spending time admiring the view, retrace your steps back to your vehicle.

Taconic Crest Trail
Border between NY and MA
MODERATE TO VERY STRENUOUS, 6–37 MILES
Getting there: The Taconic Crest Trail Northern Terminus is on Rt. 346 in North Petersburg, NY, and the Southern Terminus is on Rt. 20 in Hancock.
This 37-mile trail allows one to do multiple short to medium hikes, several long hikes, or one enormous day of hiking to complete it. According to fastestknowntime.com, someone has hiked the entire trail in under 7 hours! However, for the regular hikers among us, there are several highlights to sample without working too hard. From the Northern Terminus, you can hike up a steep climb about 2 miles to an overlook that faces east and south. From Rt. 2 at Petersburg Pass you can hike north 2.8 miles, passing a good view to the south and west, to the Snow Hole, which can hold snow into June. Heading south from Petersburg Pass, it is 2.75 miles to the summit of Berlin Mountain, the highest point in Rensselaer County with an excellent view of Mt. Greylock. There are also access trails along Oblong Road in Williamstown. From Potter Mt. Road in Hancock, it is 3.3 miles to Berry Pond in Pittsfield State Forest.

Old Mill Trail
Hinsdale
ACCESSIBLE TO EASY, 1.4–3 MILES
Getting there: The Old Mill Trail is just east of Rt. 8 on Main Street in Hinsdale.
This trail is accessible to strollers and wheelchairs, although the parking lot itself will be undergoing repairs this year to make it more accessible. This is an interpretive trail, with paper guides available at the start as well as “augmented reality videos” online. The guide and videos explain the history of the mill, as well as the natural history of the upper Housatonic River and the plants and animals found there. There is even interpretive information about the 1938 Oldsmobile found along the trail. The accessible section of the trail ends after .7 mile but the trail continues for another .8 mile, crossing Rt. 8 and following the river. The lower section of the trail follows old concrete penstock that supplied water to the downstream mills.

Keystone Arch Bridges Trail
Chester
MODERATE, 5 MILES
Getting there: The trailhead is located just off Middlefield Road, 2.5 miles north of Rt. 20 in Chester.
This trail follows the Westfield River, the first National Wild and Scenic River, and visits a series of stone arch bridges, two of which are National Historic Landmarks. These dry-laid bridges were constructed for the Western Railroad, the first railroad in America to cross a mountain. The design of the railroad was by George Washington Whistler, aka Whistler’s Father, and joined Boston to Albany in 1840. There are interpretive signs at several points along the trail which do a great job of explaining the history of the railroad and the bridges. Just north of the start, you come to the first of 5 bridges. Continue along the trail to the rest of the bridges, most of which have side trails to the water. The height of each bridge above the river increases as you walk upstream until you reach the last bridge, which towers 70 feet above the river. You can walk to the edge of this bridge, but be careful and watch pets and children. Return along the trail to your vehicle for a total of 5 miles. For more history, be sure to visit the Chester Railway Station and Museum, another National Historic Landmark.

Bartholomew’s Cobble
Sheffield
EASY TO MODERATE, UP TO 5 MILES
Getting there: Drive south past Sheffield on Rt. 7 and 7A. Turn right onto Rannapo Road and then left onto Weatogue Road.
There is a $5 non-member adult and $1 non-member child admission fee and dogs are not allowed. I have not singled out a particular trail of this Trustees of Reservations property since all of them have their own beauty and unique features. This National Natural Landmark is known for its many varieties of plants, especially its large diversity of fern species. There are also open agricultural fields, floodplain and upland forests, one of the largest cottonwoods in Massachusetts, a very fine vista with a bench, rock outcrops, and miles of trails to wander.

Appalachian Trail over Everett, Race, and Bear Mountains
Mt. Washington to Salisbury, CT
STRENUOUS, 11.2 MILES
Getting there: From Rt. 23 in South Egremont head south on Rt. 41 to the first right onto Mt. Washington Road. Take Mt. Washington Road and East Street 8.4 miles to Mt. Everett Road and a sign for Guilder Pond on the left.
This is one of my favorite hikes in the Berkshires. It’s rugged and rocky and the views are outstanding. Walk up the gated road from the Guilder Pond parking lot .5 mile to the Mt. Everett lean-to. This impressive stone-sided shelter has a fine view and is a good spot to stop and rest after the steep climb from the parking lot. For an easy hike, turn around and head back to your vehicle. To continue on the strenuous hike, follow the trail from the shelter that heads westerly to the Appalachian Trail (AT). When you reach the white paint blazes of the AT, turn left and head to the summit. The peak is mostly tree covered but there are some views to the south and southwest. Continuing south, the trail is quite steep and rocky and care should be taken. At the intersection with the Race Brook Trail on the left, continue forward and start climbing. The view from the summit and the southern portion of Race Mountain is the prize of this hike. Much of the trail is over open ledges and there are outstanding views of the Catskills, Mt. Everett, Mt. Greylock, the Twin Lakes, and the Housatonic Valley. Hiking south, one encounters another steep descent before crossing Bear Rock Stream. After another mile the trail parallels Sages Ravine, crossing the stream in several places before climbing very steeply to the summit of Bear Mountain. This is the tallest peak in Connecticut, with a stone viewing platform and more outstanding views.

Sunset Rock
Copake Falls, NY
MODERATE, 3.6–5.1 MILES
Getting there: From Rt. 22, 4 miles south of Hillsdale, NY, turn left on Rt. 344 and drive 1 mile to a large parking area on the right.
Sunset Rock is a moderate hike in Taconic State Park, just over the border in New York. (This is also the parking area for a trail to Bash Bish Falls, the highest waterfall in Massachusetts—I definitely recommend adding the 1.5 mile out and back for a beautiful scene.) From the parking lot, head back towards Copake Falls and cross a bridge over Cedar Brook. The South Taconic Trail is a right turn just after the bridge and heads uphill, following white trail markers, on an old road. Take the first right turn off the road and follow the markers and trail up to an intersection with a road. Turn right and pass a fenced area where the trail turns left and continues to climb. The South Taconic Trail follows an old road here and the hiking is very pleasant, with an even grade underfoot and a trail wide enough to walk two to three abreast. There are trails that intersect from the left, but continue following the larger white-marked trail uphill. After 1.1 miles from the road the Cedar Brook Trail, marked in blue, will intersect from the right. Make note of this as you will be following the blue markers back to your vehicle. From the Cedar Brook Trail it is another .6 mile to the Sunset Rock intersection. Turn left here and hike a short distance to an outstanding view west. Looking out over the Hudson one can see the Catskills in the distance, with the Hunter Mt. Ski Area quite obvious. To the southwest the Shawangunk Mountains are visible and the peaks of the Hudson Highlands can also be seen to the south. Retrace your steps to the Cedar Brook Trail and turn left. This trail descends steeply into a ravine with the brook at the bottom. You then follow the brook downhill, crossing it several times and passing small waterfalls. After 1.3 miles the Cedar Brook Trail ends at Rt. 344. Turn left and return to your vehicle.

Haystack Mountain
Norfolk, CT
EASY TO MODERATE, 1.2 MILES
Getting there: From Rt. 7 take Rt. 44 6.9 miles east to Norfolk. Take a sharp left onto North Street and drive .2 mile to the Park Road on the left. Drive up the winding mountain road to a parking lot.
Haystack Mountain is a very nice hike just outside of Norfolk, Connecticut. Hike on the yellow marked trail from the parking lot uphill to the summit. Although steep and rocky, the trail is only .5 mile long. When you reach an old road, turn left and continue up to the tower. The 50-foot stone tower on Haystack Mountain was built in 1929 for $50,000 and is in excellent condition. It is also listed on the National Register of Historic Places. There is a narrow, interior stairway that climbs to the top for a 360-degree view of the Litchfield Hills, the Berkshires, the Taconics, and the Green Mountains. Retrace your steps to your vehicle.

This land, and all of the present-day Berkshires, is the ancestral homeland of the Mohican people, who were forcibly displaced to Wisconsin by European colonization. These lands continue to be of great significance to the Stockbridge-Munsee Mohican Nation today. To learn more, visit mohican.com.

Illustration: Molly De St Andre / Moho Design Creative