The best road cycling routes in Berkshire County

The Ashuwillticook Rail Trail offers a delightful journey through the Hoosac River Valley, providing smooth, paved surfaces perfect for road cycling. You'll glide past the serene Cheshire Reservoir and the winding Hoosic River, with constant views of the majestic Hoosac Mountains and Mount Greylock. Keep an eye out for local wildlife like ducks, geese, and even eagles as you enjoy the gentle scenery.

This easy 27.4-mile (44.0 km) route, with only 651 feet (198 metres) of elevation gain, is suitable for all skill levels and takes about 1 hour and 47 minutes to complete. Multiple access points with parking and restrooms are available along the trail, making it easy to start your ride. It's a fantastic option for a leisurely outing, especially during the vibrant fall foliage season.

Converted from an old railroad line, the Ashuwillticook Rail Trail is a well-maintained, multi-use path that connects towns like Pittsfield, Lanesborough, and Adams. Its name, derived from an American Indian term meaning "pleasant river in between the hills," perfectly captures the charm of its surroundings. The trail even intersects with the Appalachian Trail in Cheshire, offering a unique point of interest.

If you're looking for a long, easy road cycling route with stunning views, the Cheshire Reservoir – Ashuwillticook Rail Trail Head loop delivers. This 28.8-mile (46.3 km) ride, with a minimal 522 feet (159 metres) of elevation gain, takes you through the scenic Hoosac River Valley, offering extensive views of the Cheshire Reservoir and Berkshire Pond, often with Mount Greylock in the distance. Expect smooth, paved surfaces and a chance to spot local wildlife in the wetlands and forested areas.

Starting from the Western District HQ in Pittsfield, this loop connects to the Ashuwillticook Rail Trail, which is known for its accessibility and well-maintained path. You'll find amenities like parking and seasonal restrooms at various trailheads along the rail trail. This route is best enjoyed during the warmer months, particularly in autumn when the foliage provides a spectacular backdrop.

The Ashuwillticook Rail Trail is a prime example of a successful rail-to-trail conversion, providing a level grade that makes it accessible for all ages and abilities. Its path alongside the Cheshire Reservoir and Hoosic River makes it a favored spot for birdwatching, with opportunities to see ducks, geese, and even ospreys. This route offers a unique blend of natural beauty and historical significance, making it a standout road cycling option in the Berkshires.

The Ashuwillticook Rail Trail Head – Cheshire Reservoir loop from Adams offers a varied and rewarding road cycling experience. You'll start on the pristine, paved Ashuwillticook Rail Trail, enjoying flat, scenic stretches through the Hoosic River valley with views of Mount Greylock and the tranquil Cheshire Reservoir. However, don't let the rail trail fool you; this is a difficult 38.1-mile (61.2 km) loop with a substantial 3370 feet (1027 metres) of elevation gain, making it a true test for road cyclists. Expect to spend around 3 hours and 6 minutes navigating its diverse terrain, from smooth asphalt to challenging climbs around the reservoir.

To tackle this loop, plan your visit during fair weather, as the significant elevation gain can be more demanding in adverse conditions. The trailhead in Adams provides convenient parking, making it easy to start your adventure. While the rail trail sections are generally easy, the overall difficulty of the Ashuwillticook Rail Trail Head – Cheshire Reservoir loop cycling means you should be well-prepared with appropriate gear and hydration for the longer, more strenuous sections.

This route stands out for its blend of natural beauty and historical context. The Ashuwillticook Rail Trail follows a former railroad bed, offering glimpses of old mill buildings and varied landscapes including wetlands and forests. The Cheshire Reservoir section is particularly noted for its tranquil beauty and opportunities to spot wildlife like osprey and herons. The town of Adams even embraces the trail with unique local charm, featuring banners depicting a black bear riding a bicycle, a nod to both the trail and local wildlife.

This challenging road cycling loop takes you from the cultural hub of the Clark Art Institute in Williamstown directly into the heart of the Berkshire Mountains, culminating in the formidable ascent of Mount Greylock. You'll experience a dramatic shift from scenic, rolling roads to the steep, winding climb through deep woods, with the reward of panoramic vistas from Massachusetts' highest peak. The route offers a unique blend of athletic endeavor and picturesque New England scenery, making it a memorable ride for those seeking a true test.

Planning your visit means preparing for a serious climb; Mount Greylock is renowned as the state's toughest. While the paved roads are generally well-maintained, the descent, especially on Notch Road, demands caution due to its steep grades and hairpin turns. There are no specific permits required for cycling, but always check local conditions and weather, particularly during shoulder seasons, as mountain weather can be unpredictable. Starting your ride early in the day is advisable to make the most of daylight and avoid potential afternoon traffic.

What makes this route truly stand out is its combination of a world-class art institution and an iconic natural landmark. The Clark Art Institute's beautiful campus provides a serene starting point, contrasting with the rugged, forested slopes of Mount Greylock. This loop isn't just about the physical challenge; it's an opportunity to connect with both the cultural and natural heritage of the Berkshires, offering stunning viewpoints towards the New York border and the Green Mountains of Vermont from the summit.

The Mount Greylock loop from The Clark Art Institute offers a demanding road cycling adventure, leading you through the scenic Mount Greylock State Reservation. You'll navigate winding roads and deep woods before the landscape opens up to reveal expansive panoramic views from the summit, a truly rewarding experience for any cyclist. This difficult route covers 24.3 miles (39.1 km) with a substantial 2993 feet (912 metres) of elevation gain.

Plan your ride between late May and mid-October, as the summit roads are typically closed outside these months. Starting from The Clark Art Institute provides convenient parking, but remember that conditions at the summit can be much colder and windier than at the base. It's wise to pack a windbreaker for the descent, which features steep sections and hairpin turns requiring your full attention.

This route takes you to the highest point in Massachusetts, making it an iconic climb for road cyclists. The historic Bascom Lodge at the summit offers a place to rest and enjoy the views, adding to the experience. The area's cultural connection, with The Clark Art Institute as your starting point, blends art and nature seamlessly.