4.5
(4)
34
hikers
07:10
24.0km
700m
Hiking
Embark on the Skyline Trail for a difficult hiking adventure that spans 14.9 miles (24.0 km) and challenges you with 2307 feet (703 metres) of elevation gain. This route offers varied terrain and continuous natural beauty, taking approximately 7 hours and 10 minutes to complete. As you hike, you will…
Last updated: April 23, 2026
Tips
Your route passes through a protected area
Please check local regulations for:
Blue Hills Reservation
Waypoints
Start point
Bus stop
Get Directions
484 m
Highlight • Forest
Tip by
5.79 km
Tip by
9.86 km
Highlight • Viewpoint
Tip by
11.5 km
Highlight (Segment) • Trail
Tip by
24.0 km
End point
Bus stop
Way Types & Surfaces
Way Types
22.9 km
923 m
104 m
< 100 m
< 100 m
Surfaces
23.0 km
564 m
188 m
111 m
< 100 m
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Elevation
Highest point (170 m)
Lowest point (30 m)
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Weather
Powered by Foreca
Today
Saturday 5 September
22°C
13°C
55 %
Additional weather tips
Max wind speed: 20.0 km/h
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This route was planned by komoot.
While the specific trailhead parking isn't detailed in the provided information, the Skyline Trail is located within the Blue Hills Reservation. You can typically find parking areas at various access points to the reservation. It's advisable to check the Blue Hills Reservation official website for designated parking lots and any potential fees or regulations before your visit.
The provided information does not indicate any specific permits or entrance fees for hiking the Skyline Trail within the Blue Hills Reservation. However, it's always a good practice to check the official Blue Hills Reservation website or local park authority for the most current regulations regarding park access.
The provided information does not explicitly state the dog policy for the Skyline Trail in Blue Hills Reservation. Generally, many trails in public reservations allow dogs on a leash, but it's best to confirm the specific pet regulations with the Blue Hills Reservation authorities before bringing your dog.
Based on general trail conditions, the best time to hike this trail would likely be during spring, summer, and fall when the weather is milder and the trails are clear of snow and ice. The provided research for a different Skyline Trail (Mount Rainier) suggests peak season for wildflowers is July and August, which could also be a beautiful time for the Blue Hills trail if similar flora is present.
While specific terrain details for the Blue Hills Skyline Trail are not provided, trails of this difficulty often feature varied surfaces. Expect a mix of dirt paths, potentially some rocky sections, and possibly some inclines and declines given the elevation changes. The overall difficulty is rated as 'difficult', suggesting challenging sections.
Along the Skyline Trail, you can discover several interesting spots. These include Saint Moritz Pond, and various viewpoints offering expansive vistas. Notably, from Buck Hill, you can enjoy a View of Miso Hill, Magoniscook Hill, Great Blue Hill, and Wolcott Hill. Another highlight is the Blue Hill Observatory and View of Boston Skyline.
Yes, the Skyline Trail is part of a network of paths within the Blue Hills Reservation. The route you're interested in covers 100% of the main Skyline Trail and also passes through sections of the Claire Saltonstall Bikeway, Red Dot Loop, North Skyline Trail, Wolcott Path, Bouncing Brook Path, Accord Path, Coon Hollow Path, South Skyline Trail, Eliot Circle, Sawcut Notch Path, Headquarters Path, Pipe Line, Breakneck Ledge Path, Dark Hollow Path, Indian Camp Path, Tucker Hill Path, Doe Hollow Path, Jeffries Trail, Buck Hill Path, Skyline Trail South, Wildcat Notch Trail, Brookwood Trail, Puddle Path, Murphy Path, Hill Path, and Saint Moritz Avenue.
This trail is rated as 'difficult' with a significant distance of over 24 km (15 miles) and an elevation gain of over 700 meters (2,300 feet). This suggests it is not ideal for beginners or young children. Experienced hikers will find it challenging but rewarding, while occasional hikers might find it very difficult. Shorter, easier trails within the Blue Hills Reservation would be more suitable for families or those new to hiking.
The estimated duration for completing the entire Skyline Trail is approximately 7 hours and 10 minutes. This is an estimate for continuous hiking and does not include breaks for rest, enjoying viewpoints, or taking photos.
The Skyline Trail offers impressive views, particularly from elevated points like Buck Hill, where you can see surrounding hills such as Miso Hill, Magoniscook Hill, Great Blue Hill, and Wolcott Hill. A major highlight is the Blue Hill Observatory, which provides a stunning panorama including the Boston Skyline on clear days.
Given its 'difficult' rating and length, it's important to be well-prepared. Ensure you have appropriate footwear, plenty of water, snacks, and layers of clothing. Check the weather forecast before you go, as conditions can change. Be mindful of the varied terrain and potential for steep sections. Always let someone know your hiking plans.
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