The Quiet Wilds: 7 Hikes Off the Beaten Path

[Editor’s Note: An earlier version of this article (which will also appear in the physical summer magazine) had errors that have since been corrected in this text. Those mistakes were mine. Bill Siever’s book contains the accurate information.]

While the trails of Bash Bish Falls and Monument Mountain are often crowded with hikers snapping selfies, there’s a quieter wilderness waiting not far away. Tucked into lesser-known corners of the region, these seven hikes are recommended by accomplished outdoorsman Bill Siever, author of 100 Hikes in the Southern Berkshires and Just Beyond. These treks offer solitude, scenery, and a sense of discovery for those willing to take the path less traveled.

When creating the guide, Siever enlisted the help of around 30 volunteers to extensively test trails and provide feedback—some recruited through an article in Rural Intelligence! His book covers information never before collected on the area, including updated and comprehensive difficulty ratings, locations of notable features, and information about accessibility for dogs, kids, and those with physical limitations.

“There’s so much history in this area,” Siever says. “I love finding connections that bring a place to life beyond its trails. And while the mountains here may be smaller, they pack a punch," Siever says. "There are just so many great long views over these old hills."

Bill Siever at the Jug End Overlook in South Egremont, Ma..

Here are seven off-the-beaten-path hikes from Siever’s guide that offer distinctly memorable experiences in the RI region:

1. Harvey Mountain – Austerlitz, NY

Distance: 4.2 miles (loop)
Difficulty: Moderate
Highlights: Summit views, blueberry fields, quiet trails

Just below Harvey Mountain's summit is one of the best panoramic views in Columbia County—without the foot traffic of better-known peaks. The ascent winds through dense forest to an open area filled with lowbush blueberry bushes. As you emerge above the treeline, look for extensive views south to the South Taconic Range and west to the Catskills. Climbing a bit higher, you’ll reach the flat, wooded summit near a stone marker at the NY/MA border.

2. Flag Rock – Great Barrington, MA

Distance: 3.6 miles (out and back)
Difficulty: Moderate
Highlights: Dramatic cliffside viewpoints of the Housatonic River valley

Flag Rock is the kind of hike that makes you wonder why more people aren’t here. A narrow trail climbs steadily from the outskirts of Great Barrington to a wide, flat ledge with sweeping views of the valley and the
Catskills across the way. Hike in the early evening for golden light that makes the pines glow. The trail offers a peaceful alternative to the more frequented paths on the eastern side of the Monument Mountain Reservation, with zero road noise.​

3. Tyringham Cobble – Tyringham, MA

Distance: 2.1 miles (loop)
Difficulty: Moderate
Highlights: Open meadow ridge, rock formations, Appalachian Trail spur

A quick but rewarding loop hike, Tyringham Cobble blends bucolic pastures and dramatic stone outcrops. Maintained by The Trustees of Reservations, the cobble itself is a narrow, lichen-covered ridge that offers elevated views of the village and surrounding forests. The Appalachian Trail cuts through the preserve, and hikers can tack on a longer walk through beautiful open meadows to the south of the Trustees’ property. The area is rich in history and offers a serene hiking experience.​

4. Great Mountain Forest – Norfolk, CT

Distance: Varies by trail (suggested 4 to 5 mile loop)
Difficulty: Moderate
Highlights: Old-growth forest, glacial ponds, quiet trails

This 6,200-acre park sprawls across two towns in northwest Connecticut and features a thriving moose population and New England’s southernmost black spruce bog. Start at the east entrance and choose from trails like the Charcoal Pit Trail or the Crissey Trail. You'll pass hushed ponds, mossy boulders, and stands of tamarack and hemlock. It's a place where you can truly feel the ecological richness of the Litchfield Hills—and maybe not see another soul.​

5. Mary Moore Preserve – Sharon, CT

Distance: 2.5 miles (partial loop)
Difficulty: Easy to Moderate
Highlights: Lookout point, mature oak forest, low traffic

This gently rising trail leads hikers to the Moore Lookout, a serene perch overlooking the undulating farmland of northwestern Connecticut, the southern Berkshires, and the Hudson Valley. Mary Moore sits beside the Hamlin Preserve and offers a patchwork of mature oak stands, rocky outcrops, and open field edges. You’re more likely to hear pileated woodpeckers than human voices here. The trail is well-maintained and offers a peaceful retreat into nature.​

6. Overmountain Conservation Area – Ancram, NY

Distance: 2.1 miles (Gentian Hill and Kite Hill loops)
Difficulty: Moderate
Highlights: Wide-open meadow trails, views of the Catskills and South Taconics

With expansive fields, an old red barn, and trails that climb gently toward sweeping ridgetop vistas, Overmountain Conservation Area is pure Hudson Valley charm. The Gentian Hill Loop is especially scenic in late summer, when wildflowers bloom beneath open skies. From the top, views extend to the South Taconics and beyond. The area is managed by the Columbia Land Conservancy and offers a variety of habitats to explore.​

7. Brace Mountain via Mt. Frissell – CT/MA/NY

Distance: 4.3 miles (out-and-back)
Difficulty: Challenging
Highlights: Highest point in Connecticut, three-state convergence point, alpine feel

This trail crosses through three states and multiple ecological zones. Starting in Massachusetts, you’ll ascend through hardwood forest to the craggy summit of Mt. Frissell, touch Connecticut’s high point (not the summit, oddly), and continue to the grassy crown of Brace Mountain. The open summit offers a rare sense of high elevation in the region, with views over the Harlem Valley, Catskills, and Berkshires. A notable feature is the tri-state marker where Connecticut, Massachusetts, and New York meet, providing a great photo opportunity at the spiritual center of the RI Region.