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

Dudley Barrows Trail

Easy

2.9

(24)

25

runners

Dudley Barrows Trail

00:22

3.07km

30m

Running

An easy 1.9-mile (3.1 km) jogging route through Dudley Barrows Woods, featuring rocky terrain, ridge line views, and the Dudley Farm Barn.

Last updated: February 26, 2026

Waypoints

A

Start point

Parking

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1

1.46 km

Dudley Farm Barn

Highlight • Historical Site

The Dudley Barrows Woods are situated around the property of Dudley Farm and feature a couple miles of quiet trails that are popular for walking and jogging. There are a …

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3.07 km

End point

Parking

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Way Types & Surfaces

Way Types

2.90 km

160 m

Surfaces

2.85 km

154 m

< 100 m

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Elevation

Elevation

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Weather

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Today

Sunday 12 July

28°C

16°C

0 %

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Max wind speed: 9.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

Is the Dudley Barrows Trail suitable for beginner trail runners?

While the komoot tour classifies this route as 'easy' for jogging, the terrain includes a 'rocky highland' section known as The Three Monks and a ridge line with 'lots of climbing'. This means you should expect uneven surfaces and elevation changes. It's a great trail for those looking to transition from road running to trail running, offering a moderate challenge.

What kind of terrain can I expect on this trail?

You'll encounter varied terrain, including a 'rocky highland' section called The Three Monks and a ridge line that involves 'lots of climbing'. The trail is part of the 120-acre Dudley Barrows Woods, offering a natural, unpaved surface that requires good, comfortable shoes.

Where can I park to access the Dudley Barrows Trail?

Access points for the trail are available from Dudley Farm, Renee's Way, and Hoop Pole Road. Parking is typically available at these access points, though it's always good to check local signage.

Is the Dudley Barrows Trail a loop?

Yes, the komoot tour for the Dudley Barrows Trail is designed as a loop run, allowing you to experience the full route without retracing your steps.

Are there any notable sights or viewpoints along the trail?

Absolutely! The trail offers 'sweeping autumn views' from the ridge line, which rises over the tree canopy and crosses the three 'balds' of The Three Monks. You'll also pass by the historic Dudley Farm Barn, a notable highlight along the route.

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

The trail is particularly beautiful in the autumn, offering 'sweeping autumn views' from its ridge line. However, it provides a 'beautiful oasis of tranquility' year-round. Be mindful of seasonal conditions, especially in winter, as rocky terrain can become slippery.

Is the Dudley Barrows Trail dog-friendly?

The Dudley Barrows Woods, where this trail is located, is managed by the Guilford Land Conservation Trust (GLCT). Generally, GLCT properties are dog-friendly, but dogs must be kept on a leash and owners are responsible for cleaning up after their pets. Always check for specific signage at the trailhead.

Do I need a permit or pay an entrance fee to use the Dudley Barrows Trail?

No, the Dudley Barrows Trail is part of the Dudley Barrows Woods, which is managed by the Guilford Land Conservation Trust (GLCT). There are no permits or entrance fees required to access and enjoy this trail.

Does the trail intersect other well-known paths?

Yes, the route also passes through sections of the Dudley Barrows, Three Monks, White Trail, Red Trail, and Cross Trail, offering a diverse experience within the Dudley Barrows Woods.

What should I wear or bring for a jog on this trail?

Given the 'rocky highland' and 'lots of climbing' sections, good, comfortable trail running shoes with adequate grip are highly recommended. Dress in layers suitable for the weather, and consider bringing water, especially on warmer days, as there are no water sources directly on the trail.

What is the 'Insider Tip' for jogging the Dudley Barrows Trail?

For the most rewarding experience, plan your visit during the autumn months. The ridge line offers spectacular 'sweeping autumn views' over the tree canopy, especially from the three 'balds' of The Three Monks. Starting your jog from the Dudley Farm access point allows for a pleasant warm-up before tackling the more challenging, rocky sections.

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