Explore Chaplin, CT
Chaplin at a Glance
Part of Windham County
If you’re looking for the best hiking trails in Chaplin this is the complete guide to all the long trails, waterfalls, and history it has to offer.
Chaplin has well over 500 acres of protected land hosting:
- 11 hiking areas for 8.4 miles of hiking trails
- 1 whitewater boating area
- 3 spots for fishing
- 1 disc golf course
Trails range from the wide flat out-and-backs of the Air Line to short hilly and wooded loops. The town boasts one of the best swimming holes that is not a swimming hole at Diana’s Pool as well as one of the rare whitewater runs in the state. For a more relaxed day, cast a line along the Natchaug River or try your hand at the 9 hole disc golf course at Garrison Park. Seek out the paper mill ruins, the hidden waterfall, or just pass through historic Main Street.
My Highlights
- The natural splendor of Diana’s Pool
- The Orchard Hill overlook in Goodwin State Forest
- Watching the forest regrow at Two Sisters Preserve
Hiking
Town Parks
- Garrison Park –★★– 3 miles – A small park with ball fields and a walking track with access to adjacent trails in the Hubbard Preserve and Natchaug State Forest
Land Trust
- Joshua’s Trust
- Bernard Church Woods –★– 0.5 miles – A rough trail that can be looped using quiet roads
- Harvey Preserve –★★– 1.4 miles – A simple loop with short stone ledges and an erratic
- Hubbard Preserve & Agnes’ Pasture –★★– 3 miles – Combine with Garrison Park for two short loop hikes around old fields and pastures
- Tower Hill Preserve –★★– 1.3 miles – A simple loop with homestead ruins, a seasonal waterfall, and interesting history
- Two Sisters Preserve –★★– 1 mile – A simple loop that crosses over the Air Line Trail
- Joshua’s Trust
State Parks / Forests
- Air Line Trail – 3.3 miles of the trail flow through town for easy walking with parking access at small lot near 298 Lynch Rd Chaplin, CT
- Beaver Brook State Park –★★– 0.3 miles – The entrance is in Windham and so are the pond and trail, but the undeveloped northern half lies in Chaplin
- Diana’s Pool –★★★★– 1 mile – A popular swimming hole (where swimming is prohibited) with a waterfall, the ruins of the Natchaug Paper Co., and short trails along the Natchaug River
- Goodwin State Forest –★★★★– 4 miles – The main area is in Hampton but the town has trails within the Black Spruce Pond and Orchard Hill areas
- Natchaug State Forest – ★★ – 2 miles – The southernmost block has no trails, but old forest roads lead to the main block
- Pumpkin Hill WMA — No Trails
Blue Blaze
- Natchaug Trail
- Natchaug Southern Terminus –★★– 1 mile – The entrance is in Hampton, but a nice 1 mile section of the trail between Black Spruce Pond and Orchard Hill overlook is in Chaplin
- Natchaug Trail
Boating/Fishing
- Natchaug River – Many fishing areas along the river
- Darling Pond at Garrison Park – Fishing Area
- Diana’s Pool – Whitewater run and fishing area
Disc Golf
Originally part of Joshua’s Tract (land deeded by Mohegan Chief Uncas’s son to English colonists),
The town was named in 1809 for Deacon Benjamin Chaplin, an early landowner and surveyor and a deacon of the Mansfield church. Benjamin Chaplin lived along the Natchaug River and before Chaplin died in 1795 bequeathed three hundred pounds ($1,500) to form an ecclesiastical society on the condition that this church be built within a mile and a quarter of his homestead (the church no longer stands).
It became the 124th town in the state when it was incorporated in May of 1822 from parts of Hampton, Mansfield, and Windham.
In July 1974, Chaplin Village the town’s original Main Street (now Chaplin Street) was designated a National Historic District as a good example of 19th century town planning. The town center was not near usable water power and was bypassed by railroads so was not affected by the same industrialization as other areas.
