Hiking Committee

Upcoming Activities

[Womens+] Hike to Tannery Falls and Burnett Pond

Moderate hike of ~6 miles with 500-600 ft elevation gain on the Tannery Trail to Tannery Falls (~70-80 ft waterfall). We'll take a lunch and photo break at the falls then hike back. Option to add an additional 1.8 easy miles to visit Burnett Pond on the other side of the parking area.

A.T. Hike Series 2025 Section 1

Section 1. Sages Ravine to Guilder Pond 6.7 miles, Elevation change: 1200 ft., rain date: May 4. Starting on the CT/MA border hike north on the A.T. to Sages Ravine, a beautiful, mossy gorge with cascading waterfalls and crystal-clear pools, the trail ascends steadily towards the MA border. The ravine is known for its lush forest and refreshing waters, making it a great spot for a break before the climb. From here, the A.T. climbs Mt Race (2,365 ft), offering spectacular ridgeline views to the west, with sheer cliffs dropping off to the side. This portion of the trail is exposed in places, providing breathtaking panoramas of the Taconic Mountains and the Housatonic Valley. Continuing north, the trail ascends Mt Everett (2,624 ft), the highest peak in the southern Berkshires. The climb is steep but relatively short. The summit, once home to a fire tower, still provides excellent views of the Catskills and the Hudson Valley.

Lower West River, Class 2 Whitewater

The Army Corp is scheduled to release approximately 1500 cfs of water from the Ball Mt. Dam on this weekend. This trip is going to cover the lower and easier section of this whitewater stretch of river. We will be starting at the lower end of Jamaica State Park and paddle to West Townsend. This section features some large waves and large holes most of which are avoidable with whitewater skills. Cold weather paddling gear such as a wet suit, semi-dry top may be necessary.

Mt Toby via Sugar Farms Trail

The Sugar Farms Trail is largely flat for the first two-plus miles. We then turn on to the Summit Trail which rises quite steeply along a rough, and often muddy, old woods road, arriving at the summit behind the fire tower. If the timing is right, we may see hepatica or other woodland flowers poking through.

[Womens+] Guided Wildflower Hike in the Southern Berkshires

Join us for this Women+ 4 mile, easy, guided Wildflower Hike in the Southern Berkshires. Famed for its displays of spring wildflowers, Bartholomew’s Cobble supports nearly 800 species of plants, including many rare ferns and wildflowers. Trillium, spring beauty, wild ginger, blue cohosh, toothworts, and Dutchman’s breeches are just a few of the amazing diversity of plants we can expect to see.

A.T. Hike Series 2025 Section 2

Section 2. Continuing north on our journey, the trail follows a wooded ridgeline over Mt Bushnell (2,200 ft) and other rolling terrain. As you approach Jug End Mountain, the landscape opens up to a ridgeline with breathtaking views of the Housatonic Valley and western MA. The descent from Jug End is steep and rocky, offering some of the best panoramic views in the state.

[Women's+] Sunset/Full Moon Hike to Horse Mountain and White Rocks

Hike 2-2.5 miles round trip at a relaxed pace to the White Rocks overlook, break for snacks or packed dinner, and enjoy the sunset and full moon if visible. Terrain is easy-moderate and includes moderate hills.

A.T. Hike Series 2025 Section 3

For the third section of the A.T. series, we will change direction and hike from north to south, from Home Roads to Shays' Rebellion Monument. Our trail ascends steadily through a hardwood forest toward the summit of June Mountain (1,220 ft). The climb is moderate but gains around 600 feet in elevation. While the summit area is mostly wooded, occasional openings offer scenic ridgeline views of the surrounding valleys.

[Women's+ Hike] High Ledges Wildlife Sanctuary and Massaemett Mountain

Hike is ~6-6.5 miles and includes several overlooks - Beaver Pond and the Shelburne Tower at the summit of Massaemett Mountain. Shelburne Tower features a tall narrow staircase for which headlamps are needed during the day since not all areas get sufficient light from windows. The top offers far views of the northern pioneer valley.

Searching For Woodland Treasure

Come to AMC's lovely Noble View Outdoors Center for a wildflower hike! We will walk along well-established trails for an easy hike of about 1.5 - 1.75 miles, while searching for red trillium, wood anemone, bleeding hearts, columbine and many more spring beauties. We will also traverse the All Persons Trail to view a collection of fairy houses.

Alander Mountain

We will take the Alander Mtn trail from the Mt Washington State Forest Headquarters in the South Taconics. Let's hope for a clear day; there are great views from the open summit. Bring plenty of water, lunch, and snacks. This moderately paced hike is approximately 6 miles with 1200 feet of gain.

Trails Day WMA: NH Hikes: 52WAV Mount Cube

Hike to Mount Cube out and back on the Appalachian Trail. On the NH 52 list with a view, the summit offers far views of the surrounding mountains. 7.5 miles on mixed terrain, with some steep sections including rock scrambles and approx. 2,800 elevation gain. Average pace of 2 mph with breaks to enjoy viewpoints.

National Trails Day - Cheshire Hike

Join us on National Trails Day for a hike and ice cream at Diane's Twist! We will have a table set up with information and merchandise and light snacks. Free giveaways! We will hike up to the Cobbles on the Appalachian Trail. This is an out and back hike, 3 miles total, with 920 feet elevation gain. Cobbles is considered a moderate to slightly challenging route because of the quick elevation and rocky terrain. The trail begins in a forest and steadily climbs, gradually becoming rockier as it ascends. As you continue, you can see Mt Greylock and other picturesque mountains in the distance. We'll encounter unique rock faces and formations approaching the summit.

Mount Monadnock via the Pumpelly Trail

The Pumpelly Trail is the longest trail on Mount Monadnock - a 9 mile round trip with about 1,965 feet of elevation gain. After winding through forest, the trail begins to climb, often steeply over rocks. After rising above treeline, it becomes very exposed all the way to the summit. If we are lucky, we will be able to see all the way to Boston from the top.

Hike to Upper Goose Pond Cabin

Join us for a 4.3 mile round-trip relaxed-pace hike to the cabin (725' elevation gain). The route follows the Appalachian Trail for about 0.5 mile where it crosses the Mass Pike and starts a steep uphill for about a 0.5 mile, and then levels off and descends until it reaches the blue-blazed trail that continues to the cabin. A caretaker will be at the cabin starting in May, and hopefully we can get a guided tour. Will definitely have our lunch outside on the porch or even down at the pond for some gorgeous views and possibly have a dip.