Great Blue Hill via Coon Hollow and Skyline Trail

This jogging route is relatively short, covering about 2.46 km (1.5 miles). For an average jogger, it takes approximately 21 minutes to complete, depending on your pace and how often you stop to enjoy the views.

The terrain varies significantly. The Coon Hollow Path section is generally easy with mostly paved surfaces. However, the Skyline Trail portion is more challenging, featuring rocky ascents, technical scrambles, and considerable elevation changes. You'll encounter narrow pine needle paths, root-filled sections, stone steps, and steep rock scrambles. Some parts also use carriage roads.

The Coon Hollow Path section is considered easy and suitable for all fitness levels. However, the Skyline Trail introduces moderate to strenuous sections with steep, rocky inclines. Beginners might find the full loop challenging due to the varied and technical terrain on the Skyline portion. It's advisable to be prepared for some strenuous sections.

The trail offers abundant scenic beauty. You'll find multiple hilltop viewpoints with expansive vistas. A major highlight is the nearly 360-degree panoramic view from the historic Blue Hill Observatory and View of Boston Skyline, which includes the Boston skyline, its harbor, and the South Shore. You'll also pass the Great Blue Hill Summit, the tallest point on the Atlantic coast south of Maine, and wind through forests of eastern white pines, oaks, and hickories.

Specific parking for the Coon Hollow and Skyline Trail within the Blue Hills Reservation can be found at various access points. It's best to check the Blue Hills Reservation's official website or local maps for the most current parking lot locations that provide direct access to these paths.

Yes, this jogging route utilizes sections of several other trails within the Blue Hills Reservation. You will find yourself on parts of the Coon Hollow Path, Skyline Trail, and potentially brief segments of the Claire Saltonstall Bikeway, North Skyline Trail, Eliot Circle, and South Skyline Trail.

Yes, dogs are generally allowed on trails within the Blue Hills Reservation. However, they must be kept on a leash at all times. Please remember to clean up after your pet to help maintain the natural beauty of the park.

No, there are typically no entrance fees or permits required to access the trails within the Blue Hills Reservation, including the Great Blue Hill via Coon Hollow and Skyline Trail. It is a public park managed by the Massachusetts Department of Conservation and Recreation (DCR).

Spring and fall offer pleasant temperatures and beautiful foliage, making them ideal for jogging. Summer can be warm and humid, so an early morning or late afternoon jog is recommended. Winter jogging is possible, but be prepared for potentially icy or snowy conditions on the more technical sections of the Skyline Trail.

Given the varied terrain, including rocky and root-filled sections, sturdy trail running shoes with good grip are highly recommended. Dress in layers, especially during cooler months, and consider moisture-wicking fabrics. Even though it's a shorter route, bringing water is always a good idea.

For a more relaxed jog, focus on the Coon Hollow Path section, which is generally easier. If you're looking for a challenge, the Skyline Trail offers technical ascents and descents. Be mindful of your footing on the rocky and root-filled parts of the Skyline Trail. For the best views without the crowds, consider an early morning visit.