Hike Chaplin, CT

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.




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


Disc Golf

Now go out and hike Chaplin, CT!

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   … Read more…

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 This 1.13… 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… Read more…

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… Read more…