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South Central Connecticut Planning Region

Mattabesett Trail to Lone Pine Trail Loop

Moderate

4.5

(2)

4

hikers

Mattabesett Trail to Lone Pine Trail Loop

03:36

12.7km

270m

Hiking

Hike the Mattabesett Trail to Lone Pine Trail Loop, a moderate 7.9-mile route with expansive views from Bluff Head and diverse terrain.

Last updated: February 26, 2026

Waypoints

A

Start point

Parking

Get Directions

1

2.76 km

Bluff Head Preserve

Highlight • Viewpoint

Bluff Head Preserve is a natural area located in the north of Guilford, Connecticut. Covering approximately 83 acres, the preserve offers a network of trails that wind through diverse ecosystems, including woodlands and wetlands. The highlight of the preserve is the name-giving Bluff Head, a rocky summit that provides stunning views.

Tip by

2

5.07 km

Totoket Mountain

Highlight • Summit

7.53 km

James Valley Preserve

Nature Reserve

4

10.8 km

Meyerhuber Pond

Highlight • Lake

Meyerhuber Pond sits right underneath the cliffs of Bluff Head, making it part of their spectacular view. The pond is named after the farmer who reportedly used a team of oxen to excavate what would become the pond.

Tip by

B

12.7 km

End point

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Way Types & Surfaces

Way Types

10.2 km

1.33 km

1.19 km

< 100 m

Surfaces

8.71 km

3.04 km

990 m

< 100 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 (220 m)

Lowest point (70 m)

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Weather

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Today

Saturday 6 June

30°C

15°C

27 %

Additional weather tips

Max wind speed: 22.0 km/h

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Frequently Asked Questions

How long does it typically take to hike this loop?

This loop is a challenging hike that typically takes around 3 hours and 30 minutes to 4 hours to complete, depending on your pace and how often you stop to enjoy the views. The total duration is approximately 12,944 seconds, which is about 3.6 hours.

What is the terrain like on this loop?

The terrain is quite diverse and demanding. You'll encounter a mix of shaded dirt roads, singletrack trails, and wider doubletrack sections. Expect significant elevation changes, rolling hills, and rugged, rocky segments, especially along the traprock ridges. The Mattabesett section, in particular, can be very rocky and requires sure-footedness. Some areas may also be muddy or stream-like after heavy rainfall.

What are the main points of interest or scenic views along the way?

The loop offers several picturesque spots. A major highlight is Bluff Head Preserve, which provides expansive views of the surrounding forest and the Connecticut River Valley. You'll also pass by Totoket Mountain and the serene Meyerhuber Pond. Unique features include interesting geological formations, moss-carpeted basalt beds, and even the foundations of an abandoned cottage and a horse farm along the Lone Pine section.

Where can I park to access the Mattabesett Trail to Lone Pine Trail Loop?

Specific parking details are not provided in the available data, but trailheads for the Mattabesett Trail and Lone Pine Trail are typically found in areas like Guilford, Durham, or Madison, Connecticut. It's advisable to check local land trust websites or recent trail reports for the most current parking information and directions to designated trailhead parking areas.

Is this trail dog-friendly?

Yes, the Mattabesett Trail to Lone Pine Trail Loop is generally considered dog-friendly. However, given the rugged and rocky terrain, especially on the Mattabesett section, ensure your dog is accustomed to such conditions. Always keep your dog on a leash and practice Leave No Trace principles by packing out all waste.

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

Spring and fall are often considered the best times to hike this loop. In spring, you'll see new growth and wildflowers, though some sections might be muddy from snowmelt or rain. Fall offers stunning foliage and cooler temperatures, making for a very pleasant experience. Summer can be enjoyable, but be prepared for heat and humidity, and winter hiking is possible but requires appropriate gear for icy or snowy conditions.

Are there any permits or entrance fees required for the Bluff Head Preserve?

No, there are typically no permits or entrance fees required to access the trails within the Bluff Head Preserve. It is generally open to the public for recreational use. However, always respect posted regulations and private property boundaries.

Does this loop connect to other trails?

Yes, this route is part of a larger trail system. The Mattabesett Trail is one of Connecticut's original blue-blazed trails and forms a segment of the 220-mile New England National Scenic Trail (NET). Along this specific loop, you will also traverse sections of the Lone Pine Trail (51%), Etzel Trail (26%), North Slope Connector (10%), and Old Mattabessett Trail (8%).

What should I consider bringing for this hike?

Given the moderate to hard difficulty and varied terrain, it's recommended to bring sturdy hiking boots with good ankle support, plenty of water, snacks, a map or GPS device (like komoot's app), and appropriate layers of clothing. Trekking poles can be helpful for stability on rocky or steep sections. Insect repellent is also advisable, especially during warmer months.

Is this loop suitable for beginner hikers?

This loop is generally rated as moderate to hard in difficulty due to its length, significant elevation changes, and rugged, rocky terrain. While not impossible for beginners, it is best suited for those with some hiking experience and a good level of fitness. Beginners might find certain sections, particularly the Mattabesett Trail, quite challenging.

What makes the geology of this trail unique?

The trail traverses areas with striking geological formations, particularly related to Connecticut's Eastern Border Fault. You'll encounter interesting rock formations, including bent rock and cliff faces with visible striations. The traprock ridges themselves are ancient formations that have resisted agricultural development, allowing centuries-old trees to thrive, offering a glimpse into the region's deep geological past.

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