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Routes
Running trails & routes
United States
Connecticut
Lower Connecticut River Valley Planning Region

Bailey Trail South Loop

Moderate

2.9

(4)

31

runners

Bailey Trail South Loop

00:41

5.73km

50m

Running

Jog the 3.6-mile Bailey Trail South Loop, a moderate route along the Hammonasset River with forest views and historic mill remnants.

Last updated: February 26, 2026

Waypoints

A

Start point

Parking

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1

1.25 km

Bailey Trail: South

Highlight (Segment) • Trail

The Bailey Trail is separated into two different sections: a North trail and a South Trail. The northern section is super short which this South path is over a mile in one direction. The path follows along with the river

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B

5.73 km

End point

Parking

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Way Types & Surfaces

Way Types

4.41 km

1.32 km

Surfaces

4.41 km

1.32 km

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Elevation

Elevation

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Weather

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Today

Saturday 23 May

16°C

9°C

64 %

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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 Bailey Trail South Loop?

While specific parking details aren't provided in the trail data, most trails managed by the Madison Land Conservation Trust typically have designated parking areas near their trailheads. Look for signs indicating public access points for the Bailey Trail South Loop.

Is the Bailey Trail South Loop dog-friendly?

Yes, the trail is dog-friendly. However, dogs must be kept on a leash, and owners are responsible for picking up after their pets.

Are there any permits or fees required to use this trail?

The Bailey Trail South Loop is managed by the Madison Land Conservation Trust. Generally, trails managed by land trusts are free to access and do not require permits, but it's always good practice to check their official website for any specific regulations or donation requests.

When is the best time of year to jog the Bailey Trail South Loop?

The trail offers beauty year-round. However, consider visiting during drier periods, as sections can become boggy or wet, and river crossings over rocks can be slippery, especially after rain or during high water times. Winter offers unique views of moss-covered rocks and flowing streams.

What is the terrain like on this jogging route?

The terrain is generally easy to moderate, featuring a mix of flat paths and some small inclines. Be prepared for challenging sections with abundant tree roots and rocks. You'll also encounter spots where you need to navigate over large, potentially slippery rocks to cross small river run-offs, and some areas can be boggy or wet.

Is the Bailey Trail South Loop suitable for beginner joggers?

While categorized as 'easy to moderate,' beginner joggers should be aware of some challenging sections. These include areas with numerous roots and rocks, and one 'black rated spot' that is notably steep and rocky. River run-offs can also add a moderate challenge, especially when rocks are slippery.

What natural features or landmarks will I see along the route?

You'll enjoy picturesque forest views with diverse tree species and an understory of laurel. The trail follows the Hammonasset River, offering views of its varied character, including rapids and a mini-waterfall. Look for features like Ivy Island, moss-covered rock outcrops, old stone walls, and the remnants of a 17th-century lumber mill with its dam and flume. The route also includes a footbridge over Cider Mill Brook.

Does this route connect with other trails?

Yes, the route primarily follows the Bailey Trial South and also passes through sections of the Shepherds Trail. It also connects to the Cider Mill Spur Trail, offering options for varied or longer routes.

What should I wear or bring for jogging on this trail?

Given the varied terrain, including roots, rocks, and potentially wet or boggy sections, sturdy trail running shoes with good grip are recommended. Dressing in layers is advisable, and consider waterproof footwear if jogging after rain or during wet seasons due to potential slippery rocks and boggy areas.

How long does it typically take to jog this loop?

The Bailey Trail South Loop is approximately 5.7 kilometers (3.5 miles) long. For an average jogger, it typically takes around 40 minutes to complete the loop, depending on pace and trail conditions.

What is the highlight of the Bailey Trail South Loop?

A significant highlight of this route is the Bailey Trail: South section itself, which offers scenic river views and a mix of forest and historical elements, including the remnants of an old lumber mill.

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Hammonasset Point via Hammonasset Beach loop

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