Lenox Outdoors! Tour

Roaring Brook Trail

This 2.4-mile moderately trafficked out-and-back trail features a waterfall and is rated moderate (396-foot elevation gain). The trail is used for hiking, walking, nature trips, and snowshoeing and is accessible year-round. Dogs can use the trail. The trail starts at New Lenox Road at Gate 16 and follows the access road before running south to the junction with Roaring Brook Foot Path. After crossing a stream, the trail follows the flow of another stream then turns left to cross a footbridge. The trail traverses a rough stretch to its end at Lenox-Whitney Place Road. Along the way, visitors can view Striped Maple and Eastern Hemlock trees. Find directions and learn more at this link.

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Decker Boat Ramp

Decker Boat Ramp is a great place to canoe or kayak any day of the week. The area is perfect for wildlife viewing. Some have even reported seeing beavers. The ramp makes getting your boat into the water a breeze. Check out this relaxing and pleasant spot on a hot day. Ideal for beginning paddlers who want to take in scenic views. Visit this link to see more photos on Google maps.

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Mahanna Cobble

Mahanna Cobble Trail is 3.2 miles long and strenuous due to elevation changes. The trail offers gorgeous views from George’s stone bench, named for Berkshire Natural Resource Council’s founder, George Wislocki. For the 2021 hiking season, find parking at Bousquet Sport (100 Dan Fox Drive). Park in the designated location and cross the road carefully, then follow signs and the pedestrian corridor. Once on the trail, enjoy grassy ledges with uninterrupted views south over Kennedy Park and Yokun Ridge. The approach back down allows bird’s eye views of Pittsfield and the Northern Berkshires. Dogs are welcome on BNRC property and Bosquet’s when it is not ski season, always under an owner’s immediate control. Learn more at this link.

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Pleasant Valley Wildlife Sanctuary

Set in the middle of a more than 1,000-acre setting, Pleasant Valley’s seven miles of trails wind through forests, meadows, wetlands, and the slopes of Lenox Mountain. This is an excellent site for hiking, from a 1/3-mile universally accessible trail and boardwalk to the easy Pike’s Pond Loop Trail to more strenuous hikes to the summit of Lenox Mountain (2,126 feet). The sanctuary has a new, modern welcome facility with an accessible picnic area, family-friendly and gender-neutral restrooms, hands-on educational exhibits, and a deck for sitting and relaxing. No dogs allowed. Naturalist-guided hikes and canoe trips, as well as educational programs for children, adults, and families, are hosted here by Mass Audubon. Sample programs include Berkshire Nature Camp (ages 3-15), bird walks; and a firefly watch. See program details and times here.

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Kennedy Park

Kennedy Park is a 500-acre multi-use area with trails suitable for hiking, cross-country skiing, and snowshoeing. It is treasured as one of the premier places in Berkshire County to mountain bike; motorized vehicles, electric bicycles, and snowmobiles are prohibited. The park consists of hardwood forests with old carriage roads for easy walking as well as more challenging single tracks, where you may see the occasional horse. Trails are well-maintained and groomed for winter by the town of Lenox and volunteers from Berkshire New England Mountain Biking Association. Come for a quick hike or a longer one as your schedule permits. A trail map is available at The Arcadian Shop and on the Town of Lenox’s website. Start at the Arcadian Shop, whose staff can give updates on conditions and suggest routes.

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Undermountain Rest

Contemplate the stunning vista that is Parsons Marsh. Look for the bench opposite Undermountain Stables at 400 Undermountain Road with a sign that says You Can Sit Here. Bring a sandwich and soak up the view to Parsons Marsh and Monument Mountain. Although not wheelchair-accessible, this “hike” is just six steps up and a few strides to the right to reach the bench at the “summit.” In 2012, Berkshire Natural Resources Council was given a small building lot at the head of Parsons Marsh. From the front of this parcel, passersby can see the entire expanse of Parsons Marsh. For years artists and photographers trespassed to get the best views, now the sign and bench ensures all are welcome! Next time you’re walking Undermountain Road, step off and enjoy the views. Learn more at this link.

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Parsons Marsh Reserve

Parsons Marsh is part of the Undermountain Valley, a wetland and forest in the heart of Lenox. Berkshire Natural Resources Council, the Town of Lenox, and private landowners partnered to conserve this land for farmland, wildlife habitat, and recreation. The 183-acre site now offers a fully accessible trail consisting of half hard-packed surface and half boardwalk, encouraging all visitors to enjoy the wetlands and woodlands and observe diverse plants and animals. This is the first Berkshire Natural Resource Council property not open to hunting or fishing. On the 1,800-foot (1/3-mile) accessible trail, visitors will wind through an open meadow to a small pond, then into forested upland and vegetated wetland that provides views of this large marsh as well as opportunities to sit and experience each habitat. Rest on the bench or picnic on the accessible table on a spur trail near the pond. Just beyond the pond, the trail transitions to a boardwalk as it enters the forested wetland. Take note of the large birch trees and their raised root systems covering the forest floor. The trail ends at an observation platform providing open views from the edge of the marsh. Find directions to the trail at this link

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Olivia’s Overlook

Olivia’s Overlook is the center of the 734-acre Yokun Ridge Reserve. This popular overlook is also the trailhead for six miles of hikes. The Charcoal Trail (1.6-mile loop) is named for the flat, rounded charcoal pits along the way. The trail provides views of Monument Mountain, Richmond, and West Stockbridge. The Brothers Trail connects Charcoal Trail to Old Baldhead Road on the other side of Lenox-Richmond Mountain Road. Old Baldhead leads to Monks Pond, which once served as the Shadowbrook reservoir and owes its name to the Jesuit successors of Shadowbrook’s original owner. The Burbank Trail (3.2 miles) begins across the road from Olivia’s Overlook. This land, and all the present-day Berkshires, are the ancestral homeland of the Mohican people, forcefully displaced to Wisconsin by European colonization. These lands continue to be of great significance to the Stockbridge-Munsee Mohican Nation today. Visit this link to learn more

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Want a great view? Go to Olivia’s Overlook

Stevens Glen Trailhead

A 1.2-mile hike through a 129-acre area, this hike brings you to one of Lenox’s most dramatic sights: Lenox Mountain Brook cascading down a steep rocky ravine with an observation deck that makes it accessible and recalls the glen’s history as a destination for carriage-goers more than a century ago. Visitors walk under white pines and majestic hemlocks that replaced the American chestnuts removed to stop the devastating chestnut blight. The eastern portion of the trail has been closed due to erosion at stream crossings. Stay on the western side and adhere to closure signs if present. At the viewing platform, sit on a bench and reflect on the stream or cool your feet on a hot day. The trip takes about one hour and is rated moderate. Get directions and learn more at this link

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Stockbridge Bowl

Stockbridge Bowl, also known as Lake Mahkeenac, is a 372-acre artificially impounded water body in Stockbridge, near Lenox. It offers sweeping views to the north of Tanglewood, the summer home of the Boston Symphony Orchestra, and a public beach and boat ramp, accessible to all. Any vessel launched here must be thoroughly washed first to remove Zebra mussel contamination. The lake is used by scullers, canoers, kayakers, sailors, swimmers, water skiers, powerboaters, and fishermen; Jet-skis are forbidden.. Swimming is safe and the water is clean and clear. January to March, if the lake is frozen, ice-fishing is common. The State stocks it with trout twice yearly and there is a high population of freshwater fish. Visitors often spread a picnic blanket on the lawn syrrounding the beach to get out of the sand and enjoy the scenery. See more images at this link.

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Edith Wharton Park

This 22-acre park on the western shore of Laurel Lake is accessible from Laurel Lake Road off Plunkett Street in Lenox. The park is part of the original property purchased by famed author Edith Wharton when she designed her palatial residence here in 1902. Edith Wharton was an American novelist, short story writer, and designer, whose insider’s knowledge of New York aristocracy realistically portrayed the lives and morals of the upper-class during the Gilded Age. In 1921, she became the first woman to win the Pulitzer Prize in Literature for novel The Age of Innocence. Among her other well-known works are The House of Mirth and Ethan Frome.

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Black Swan Boat Rental

Check out the Black Swan Inn, a private hotel that makes available to the public (not limited to guests), rentable boats and kayaks. Take your family out on a motorized pontoon boat for a one-hour to four-hour cruise around Laurel Lake or go solo or tandem for one to three hours on their single, tandem, or pedal kayaks. With Adirondack seats perfect for lounging, this quaint hotel is a great way to get into a Berkshires state of mind. Learn more about rates and availability on their website.

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October Mountain

At 16,500 acres, October Mountain is the largest state forest in Massachusetts. Visit to trek on trails suitable for all levels of hiking experience. One of the most scenic leads through Schermerhorn Gorge, a striking natural feature that has intrigued geologists for generations. The park is open from sunrise to one half-hour after sunset. Learn more at this link.

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Woods Pond

At an elevation of 945 feet, Wood Pond is a beautiful reservoir surrounded by easy trails to hike, bike, walk, or jog and has a launching area for kayaks and canoes. Paddlers call the pond a great place to observe birds and wildlife, including beaver, blue heron, geese, ducks, and eagles. Some come to fish, including ice fishing in winter. Visitors have reported catching fallfish, Brook trout, Brown trout, shad, bass, and pickerel. See photos on Google maps.

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Arcadian

The Arcadian Shop has been a leader in the outdoor industry since 1974. Located in Lenox, the store specializes in several aspects of outdoor recreation, with experts available in biking, hiking, camping, kayaking, cross-country skiing, telemark, snowshoeing, running, climbing, and fashion and function clothing, to name a few. Pre-COVID the shop also rented hybrid, mountain, and road bikes, as well as equipment for kayaking, paddleboarding, cross-country skiing, and snowshoeing. Nestled next to the 400-acre Kennedy Park, they have hiking and biking access right out their back door, and a cafe to relax in when you’re done. Visit the shop’s website.

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