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Routes
Hiking trails & Routes
Norfolk County
Milton

Wolcott Hill Loop Trail

Easy

5.0

(1)

6

hikers

Wolcott Hill Loop Trail

01:07

3.69km

110m

Hiking

Embark on the Wolcott Hill Loop Trail for an easy hike spanning 2.3 miles (3.7 km), with a gentle elevation gain of 366 feet (112 metres). You can complete this peaceful woodland ramble in about 1 hour and 6 minutes. As you hike, you will pass through majestic stands of…

Last updated: April 23, 2026

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Your route passes through a protected area

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Waypoints

A

Start point

Parking

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1

1.02 km

Blue Hill Observatory and View of Boston Skyline

Highlight • Viewpoint

Take a hike to the summit of Great Blue Hill and the observation tower close by that offers a stunning 270° view of Boston, its harbour and to the South …

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2

1.52 km

Wolcott Hill

Highlight • Summit

Although there are no far-reaching views from Wolcott Hill, it's still one of the taller peaks in the Blue Hills Reservation, standing at 133m (433ft).

As you wander through, you …

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B

3.69 km

End point

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Way Types & Surfaces

Way Types

2.53 km

1.14 km

< 100 m

Surfaces

1.67 km

827 m

800 m

389 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 (180 m)

Lowest point (70 m)

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Weather

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Today

Tuesday 26 May

29°C

12°C

0 %

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Max wind speed: 14.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

Where can I park to access the Wolcott Hill Loop Trail?

You can easily access the trailhead from the Trailside Museum's north parking lot within the Blue Hills Reservation. This is a convenient starting point for your hike.

Is the Wolcott Hill Loop Trail dog-friendly?

Yes, this trail is considered dog-friendly, making it a great option for hiking with your canine companion. Please ensure your dog is leashed and you follow all park regulations.

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

The trail offers diverse scenery throughout the year. While specific seasonal conditions are not detailed, the peaceful forest and views can be enjoyed in most seasons. Consider spring for wildflowers or autumn for foliage.

Are there any permits or entrance fees required for hiking in Blue Hills Reservation?

Generally, there are no entrance fees or permits required for day-use hiking in the Blue Hills Reservation. However, it's always a good idea to check the official mass.gov website for any updated regulations or specific event requirements.

Is this trail suitable for beginners or families?

Yes, the Wolcott Hill Loop Trail is generally suitable for families and is often described as a moderate hike, making it a good choice for those new to hiking or looking for a less strenuous outing. Some sources even classify it as easy.

What is the terrain like on the loop?

The trail offers diverse scenery and rolling terrain. You'll gradually climb through shady pine and hemlock forests. Be aware that the eastern side of the route, in particular, features uneven footing and loose rock, so caution is advised, especially in wet conditions.

What notable features or viewpoints can I expect to see along the route?

Along the way, you'll experience a pleasant woodland ramble through majestic stands of pines and hemlocks. A significant feature is Wildcat Notch, where a break in the trees provides clear views of the northeastern slope of Great Blue Hill. You can also enjoy views of the Boston Skyline from the Blue Hill Observatory and reach the Wolcott Hill summit.

How long does it typically take to complete the loop?

The loop is approximately 2.2 to 2.5 miles (3.6 km to 4.0 km) long. It can take around 56 minutes to 1.75 hours to complete, depending on your hiking pace and how often you stop to enjoy the scenery.

Does the route intersect with other trails?

Yes, the route also passes through sections of the Skyline Trail, the Claire Saltonstall Bikeway, Wolcott Path, and the North Skyline Trail, offering connections to other parts of the Blue Hills Reservation.

What kind of nature and wildlife might I encounter?

Hikers can expect peaceful forest scenery, wildflowers, and opportunities to observe local wildlife. Near marker 1092, you might also encounter a vernal pool, adding to the natural diversity.

Are there any specific sections of the trail that require extra caution?

Yes, the eastern side of the route is noted for having uneven footing and loose rock. It's advisable to exercise extra caution in this area, particularly if conditions are wet, to ensure a safe hike.

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