Nine Men's Misery, Homestead, and Whipple Trails loop
Nine Men's Misery, Homestead, and Whipple Trails loop
3.2
(2)
25
hikers
01:19
4.99km
50m
Hiking
Hike an easy 3.1-mile loop through historic woodlands and fields at Cumberland Monastery, featuring the Nine Men's Misery Monument.
Last updated: February 26, 2026
Waypoints
Start point
Parking
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173 m
Highlight • Historical Site
Tip by
1.21 km
Highlight • Monument
Tip by
4.99 km
End point
Parking
Way Types & Surfaces
Way Types
3.62 km
788 m
550 m
Surfaces
3.62 km
1.34 km
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Elevation
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Weather
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Today
Tuesday 19 May
33°C
17°C
26 %
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Max wind speed: 18.0 km/h
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This route was planned by komoot.
This easy loop typically takes around 1 hour and 19 minutes to complete. This estimate is for continuous hiking and may vary based on your pace and how much time you spend exploring the historical sites along the way.
The terrain on this loop is generally easy, consisting of crushed stone and hard-packed earth paths. You'll find yourself walking through peaceful woodlands and open fields, with minimal elevation changes, making it suitable for most fitness levels.
This loop is rich in history and natural beauty. You'll pass by the Cumberland Monastery and Public Library, which was once a Cistercian monastery. A significant highlight is the Nine Men's Misery Monument, considered the oldest veterans' memorial in the U.S., marking a somber historical event from King Philip's War. You'll also see remnants of the monks' former quarry and serene forest paths, wetlands, and wildflowers.
Parking is generally available at the Cumberland Monastery property, which now houses the public library. Look for designated parking areas near the trailhead. Specific details on parking availability can often be found on the Town of Cumberland's website.
Yes, the trails at Cumberland Monastery are generally dog-friendly. However, it's always best to keep your dog on a leash and practice Leave No Trace principles by cleaning up after your pet.
The loop can be enjoyed year-round. Spring offers blooming wildflowers, summer provides lush greenery, fall showcases vibrant foliage, and winter can offer a peaceful, snow-covered landscape. Consider visiting during cooler months for a more comfortable hike, especially if you prefer to avoid summer heat and insects.
No, there are typically no permits or entrance fees required to access the hiking trails at the Cumberland Monastery property. The trails are open to the public for recreational use.
Yes, this loop is part of an extensive network of paths within the Cumberland Monastery grounds. The route also passes through sections of the Nine Men's Misery Trail, Beauregard Loop, Whipple Trail, Homestead Trail, and Monk's Quarry Trail, among others, offering opportunities for longer exploration.
The Nine Men's Misery Monument marks the site where nine colonial militiamen were captured, tortured, and killed by Narragansett warriors during King Philip's War in 1676. A stone cairn was erected that same year to mark their burial place, making it the oldest veterans' memorial in the United States. It's a poignant reminder of the tumultuous history between Native Americans and English settlers.
Yes, this loop is considered an easy hike with minimal elevation changes, making it very suitable for families with children. The varied scenery and historical points of interest can also make it an engaging experience for younger hikers.
The trailhead is located on the property of the former Cumberland Monastery, which now houses a public library. While there are no dedicated trail facilities like restrooms or water fountains directly on the trail, the proximity to the public library might offer some amenities during operating hours. For other services like cafes or restaurants, you would need to venture into the nearby town of Cumberland.