2.9
(4)
31
runners
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
Start point
Parking
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1.25 km
Highlight (Segment) • Trail
Tip by
5.73 km
End point
Parking
Way Types & Surfaces
Way Types
4.41 km
1.32 km
Surfaces
4.41 km
1.32 km
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Elevation
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Saturday 23 May
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9°C
64 %
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Max wind speed: 14.0 km/h
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This route was planned by komoot.
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.
Yes, the trail is dog-friendly. However, dogs must be kept on a leash, and owners are responsible for picking up after their pets.
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.
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.
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.
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.
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.
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.
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.
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.
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.