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Hiking trails & Routes
United States
Massachusetts
Norfolk County
Milton

Hancock Hill and Jeffries Trail Loop

Easy

4.7

(6026)

8,307

hikers

Hancock Hill and Jeffries Trail Loop

00:50

2.62km

100m

Hiking

The Hancock Hill and Jeffries Trail Loop offers a refreshing, easy hike, perfect for a quick escape into nature. You'll navigate a pleasant path that winds its way up to the summit of Hancock Hill, providing a satisfying sense of accomplishment without demanding too much effort. This 1.6-mile (2.6 km)…

Last updated: June 9, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

Waypoints

A

Start point

Parking

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1

580 m

Hancock Hill

Highlight • Summit

Hancock Hill may not be the tallest or most popular summit in the reservation, but its tree-covered peak offers some of the most stunning views of Downtown Boston. Unlike other …

Tip by

1.02 km

Hemenway Hill

Peak

B

2.62 km

End point

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Way Types & Surfaces

Way Types

2.35 km

265 m

Surfaces

2.45 km

164 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (140 m)

Lowest point (60 m)

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Weather

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Today

Wednesday 8 July

26°C

15°C

0 %

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Max wind speed: 8.0 km/h

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Frequently Asked Questions

How long does it take to hike the Hancock Hill and Jeffries Trail Loop?

This loop is designed to be a relatively quick hike. Based on its distance and elevation, most hikers can expect to complete the entire route in approximately 50 minutes. However, your actual time may vary depending on your pace and how often you stop to enjoy the scenery.

What is the difficulty level of this trail?

The Hancock Hill and Jeffries Trail Loop is rated as an easy hike. It features a moderate elevation gain of about 96 meters, making it accessible for most fitness levels. While some sections might be a bit rocky, it's generally suitable for beginners and those looking for a pleasant, less strenuous outdoor experience.

What kind of terrain can I expect on the Hancock Hill and Jeffries Trail Loop?

The terrain on this loop can be varied. Expect some initial steep and rocky sections, particularly around Hancock Hill, which then levels out. Sturdy footwear is recommended due to potentially rough and loose rocks in places. The trail winds through the natural landscape of Blue Hills Reservation.

Are there any notable landmarks or viewpoints along the route?

Yes, a key highlight on this route is Hancock Hill. From its summit, you can enjoy picturesque views of the surrounding Blue Hills Reservation landscape. The trail offers various points to appreciate the natural beauty of the area.

Does the trail intersect other well-known paths in Blue Hills Reservation?

Yes, the route also passes through sections of the Skyline Trail, Breakneck Ledge Path, Jeffries Trail, Chestnut Run Path, and North Skyline Trail, offering connections to a wider network of trails within Blue Hills Reservation.

Is the Hancock Hill and Jeffries Trail Loop dog-friendly?

Yes, dogs are generally welcome on trails within Blue Hills Reservation, including the Hancock Hill and Jeffries Trail Loop. However, they must be kept on a leash at all times to protect wildlife and ensure a pleasant experience for all visitors.

What is the best time of year to visit this trail?

The Hancock Hill and Jeffries Trail Loop can be enjoyed year-round. Spring offers lush greenery, while autumn provides stunning fall foliage. Summer is great for longer daylight hours, but be prepared for sun exposure as there might be limited shade. Winter hiking is also possible, but check conditions for ice or snow.

Do I need a permit or is there an entrance fee for Blue Hills Reservation?

No, there is generally no entrance fee or permit required to access the trails within Blue Hills Reservation, including the Hancock Hill and Jeffries Trail Loop. It is a public park managed by the Massachusetts Department of Conservation and Recreation (DCR).

Where can I park to access the Hancock Hill and Jeffries Trail Loop?

Specific parking for this exact loop may vary depending on your starting point within Blue Hills Reservation. Look for designated parking areas near trailheads that connect to the Skyline Trail, Breakneck Ledge Path, or Jeffries Trail, as these form parts of the loop. Always check local signage for parking regulations.

Is the Hancock Hill and Jeffries Trail Loop suitable for families with young children?

Given its 'easy' difficulty rating and relatively short duration, this loop can be suitable for families. However, be aware of the initial steep and rocky sections, especially around Hancock Hill. Sturdy shoes are advisable for everyone, including children, to navigate the varied terrain safely.

What should I bring for a hike on this trail?

For this easy loop, essential items include sturdy hiking shoes, water, and sun protection (hat, sunscreen) as shade might be limited. A small backpack for snacks and personal items is also recommended. Consider bringing a map or using a navigation app like Komoot, especially where the trail intersects other paths.

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