"100 Hikes In The Southern Berkshires" Book Launches — And Readers Helped
The comprehensive hiking guide for the Berkshires and just beyond was written with input by RI readers.
Local outdoorsman Bill Siever’s new guidebook, 100 Hikes in the Southern Berkshires and Just Beyond, showcases his passion for uncovering and sharing the hidden treasures of the area where Massachusetts, New York, and Connecticut meet. A Berkshires resident since 2006, Siever’s connection to the area began in his teenage years when his family visited Bartholomew’s Cobble in Sheffield, Massachusetts. The visit left an indelible impression, and as an adult, he returned, attracted to the landscapes and opportunities for exploration.
In 2020, Siever began the ambitious task of creating a comprehensive hiking guide for the sub-region. RI wrote about his efforts then and helped connect him with volunteers to test his hike descriptions. He says the response was overwhelming. "I had about 30 people testing trails," Siever says, adding he had one volunteer in her 80s who tested about 50 hikes for him. “She was just incredible, and we’ve all become friends through this process.”
McLennan Reservation in Tyringham, Massachusetts
Siever’s collaborative approach to trail testing was key to the book’s development. He worked with hikers of varying experience levels, asking them to verify trail conditions, directions, and features like parking areas or scenic views.
“I wanted to know, ‘If I say you can see the Catskills from this spot, is that actually true?’” he explains. Volunteers brought a variety of perspectives to the project. “Some hiked with their dogs or kids and gave me feedback I couldn’t have anticipated,” Siever adds. “I don’t have kids or a dog, so their input was invaluable in making the guide as inclusive as possible.”
The book itself includes over 60 day hikes in southern Berkshire County and dozens more in neighboring New York and Connecticut. It highlights famous landmarks like Monument Mountain and Bash Bish Falls while also featuring lesser-known gems such as Great Mountain Forest in Connecticut and Over Mountain Conservation Area in New York. Siever’s detailed maps, difficulty ratings, and seasonal tips make the guide accessible to hikers of all levels, while his thoughtful inclusion of local history adds a compelling narrative layer.
Gazebo overlooking the Catskill Mountains in Ancram, New York
“There’s so much history in this area,” Siever says, recounting stories like the purported curse on Ashintully Gardens, tied to an early 20th-century expedition to an Egyptian tomb. “I love finding these connections that bring a place to life beyond its trails.” He also emphasizes his commitment to accuracy, noting that his testers didn’t hold back when something needed adjustment. “I wanted them to tell me everything that was wrong — no sugarcoating. It’s how the book became as reliable as it is.”
Siever’s motivation for creating the guide came from a frustration with incomplete or misleading online information about the region’s trails. “This area needed a good hiking guide because the internet is full of scattered, often inaccurate information,” he says. His goal was to create a resource that locals and visitors could trust while inspiring a deeper connection to the region’s wilderness.
“I hope people not only discover new places but also come away with a greater appreciation for what makes this area so special,” Siever says.
