Hike Chaplin, CT

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 6 hiking areas for 8.4 miles of hiking trails, 1 whitewater boating area, 3 spots for fishing, and a disc golf course.



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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

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 –★★– 1 mile – 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 [/expand]

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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. [/expand]

Now go out and hike Chaplin, CT!

Harvey Preserve


68 Federal Road, Chaplin, CT, USA

Harvey Preserve Joshua’s Trust 64 acres in Chaplin, CT Parking: Small lot near 68 Federal Rd, Chaplin, CT Trail Map          Trails: 1.4 miles …

Tower Hill Preserve


122 Tower Hill Rd, Chaplin, CT, USA

Tower Hill Preserve Joshua’s Trust Property 236 acres in Chaplin, CT Parking: Medium sized pull-off near 122 Tower Hill Rd, Chaplin, CT Trail Map       Trails: 1.36 miles     Rating: ★★☆☆☆… Read more…

Natchaug State Forest Main Block


41.841980, -72.095569

Natchaug State Forest Connecticut State Forest 13,438 acres in Chaplin, Eastford, and Hampton CT Parking: Plenty of parking down the road near 243 Chaplin Rd Eastford, CT Trail Map     … Read more…

Bernard Church Woods


41.818962, -72.153062

Bernard Church Woods Joshua’s Trust 37 acres in Chaplin, CT Parking: Shoulder parking near 385 Bujak Rd, Chaplin, CT Trail Map        Trails: 0.5 miles   …

Beaver Brook State Park


483 Back Rd, Windham, CT 06280

Beaver Brook State Park Connecticut State Park 401 acres in Chaplin and Windham, CT Parking: Small lot at 483 Back Rd, Windham, CT 06280 Trail Map     …

Natchaug Trail : Morey Rd


41.8214610, -72.0970840

Natchaug Trail – Morey Rd CFPA Blue Blaze Natchaug Trail Natchaug State Forest through Chaplin and Eastford, CT Parking: Shoulder parking at 41.8214610, -72.0970840 Trail Map     …

Goodwin State Forest


41.785700, -72.083707

James L. Goodwin State Forest Connecticut State Forest 2,003 acres in Hampton and Chaplin, CT Parking: Lot at 23 Potter Rd, Hampton, CT Trail Map       …

Two Sisters Tract


41.757308, -72.145430

Two Sisters Tract Joshua’s Trust Land Trust 40 acres in Chaplin, CT Parking: Shoulder parking along busy Rt. 6 just northeast of 231 Willimantic Rd, Chaplin, CT Trail… Read more…

Garrison Park


495 Phoenixville Rd, Chaplin, CT, USA

Edward Garrison Park / Hubbard Sanctuary / Agnes’ Pasture Chaplin Town Park and Joshua’s Trust Property About 40 acres in Chaplin, CT Parking: Large lot behind Chaplin…

Diana’s Pool


20 Dianas Pool Rd, Chaplin, CT, USA

Diana’s Pool State Designated Water Access 15 acres in Chaplin, CT Parking: Small lot at 20 Dianas Pool Rd Chaplin, CT Trail Map       Trails: Less than…