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Running trails & routes
United States
Connecticut
South Central Connecticut Planning Region

Mattabesett and Lone Pine Trail Loop

Hard

4.9

(6459)

10,607

runners

Mattabesett and Lone Pine Trail Loop

02:05

16.3km

320m

Running

Jog the Mattabesett and Lone Pine Trail Loop, a difficult 10.1-mile route with 1040 feet of gain and panoramic views from Bluff Head Preserv

Last updated: February 26, 2026

Waypoints

A

Start point

Parking

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1

2.00 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, …

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16.3 km

End point

Parking

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Way Types & Surfaces

Way Types

14.8 km

1.27 km

153 m

< 100 m

Surfaces

13.3 km

1.63 km

1.33 km

< 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

Monday 6 July

19°C

16°C

94 %

Additional weather tips

Max wind speed: 18.0 km/h

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Frequently Asked Questions

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

Parking is generally available at designated trailheads that lead into the loop. A common access point is near the Bluff Head Preserve, which is a significant highlight along the route. Always check local signage for specific parking regulations.

Is this trail suitable for jogging, and what is the terrain like?

Yes, the loop is suitable for jogging, though it presents a moderate to challenging experience. You'll encounter a varied mix of surfaces, including shaded dirt roads, singletrack trails, and wider doubletrack sections. Be prepared for significant elevation changes, rolling hills, and rugged, rocky segments. Some parts can become muddy or stream-like after heavy rainfall, and you may need to cross small brooks.

Are dogs allowed on the Mattabesett and Lone Pine Trail Loop?

Generally, dogs are allowed on the trails within this area. However, it's crucial to keep them on a leash at all times to protect wildlife and ensure a pleasant experience for all trail users. Always practice Leave No Trace principles, including picking up after your pet.

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

The trail offers unique beauty throughout the year. Spring brings blossoming columbines and mountain laurel, while fall showcases vibrant foliage. Summer is popular, but be mindful of heat and humidity. Winter jogging is possible, but conditions can be challenging with ice and snow, especially on rugged sections. Be prepared for muddy conditions after rain in any season.

Do I need a permit or is there an entrance fee for the Northwoods section or other parts of the trail?

No, there are typically no permits or entrance fees required to access the Mattabesett and Lone Pine Trail Loop, including sections that pass through Northwoods. The trail connects various open spaces, including state forests and land trust preserves, which are generally free to access for recreational use. Always respect private property boundaries where applicable.

What scenic highlights or viewpoints can I expect along the route?

The loop offers picturesque scenery. You'll find sweeping panoramas from traprock ridges, providing views of forests and distant towns. The trail winds through forested areas with North American trees, moss-covered basalt beds, and vibrant flora. Notable spots include a horse farm with pastures, a pond, and a bridge over a glistening stream. The Bluff Head Preserve is particularly known for its expansive views.

Does this loop connect with other well-known trails?

Yes, the Mattabesett and Lone Pine Trail Loop is an integral part of a larger trail network. The route extensively uses the Mattabesett Trail and the New England National Scenic Trail, both of which cover significant portions of the loop. You'll also find sections of the Lone Pine Trail, Old Mattabessett Trail, and smaller connectors like the North Slope Connector and Etzel Trail.

What should I be aware of regarding the trail conditions, especially after rain?

The trail can become quite rugged and challenging, especially after heavy rainfall. Sections are prone to washing out and can become very muddy or even stream-like, making stream crossings more difficult. Proper waterproof footwear with good grip is highly recommended to navigate these conditions safely.

Are there any less ideal sections for jogging on the loop?

While most of the loop offers a natural jogging experience, one account mentions a half-mile stretch along Highway 77. This section might be less ideal for a peaceful jog due to traffic noise and proximity to the road. Be mindful of your surroundings and traffic if you encounter this segment.

Is the Mattabesett and Lone Pine Trail Loop a circular route?

Yes, as its name suggests, this is a circular loop trail. This means you will end your jog at or very near your starting point, making it convenient for parking and vehicle access.

What makes this trail loop notable or unique in Connecticut?

This loop is notable for being part of the historic Mattabesett Trail, one of Connecticut's original Blue Blazed trails, and a component of the 220-mile New England National Scenic Trail (NET). It offers a true sense of wilderness with diverse ecosystems, scenic cliffs, and rugged traprock ridges, despite its proximity to civilization. The loop also connects various preserves and features historical elements like colonial-era stagecoach roads.

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