Hike Ashford, CT

If you’re looking for the best hiking trails in Ashford this is the complete guide to all the long trails, waterfalls, and history it has to offer.

2015 Ashford Open Space Plan       Ashford Conservation Commission

Town Parks

Land Trust

  • Ashford Oak— No trails — A shell of its former glory the former champion red oak is living out its remaining days
  • Church Farm★★— 3 miles — A loop ‘Ledges’ trail on one side of Rt 89 and a ‘Meadows’ trail on the other
  • Fliegal Farm Woods— .5 miles — A short Fern Glade lollipop loop trail along the Old Connecticut Path
  • Friedman Forest★★— 2.7 miles — A self guided tree identification walk with three loop options and a heron rookery
  • Iron Mine Valley★★— 1.3 miles — An area mined for bog iron during the Revolutionary War with a short loop hike
  • Josias Byles Sanctuary★★— 1.6 miles — A loop hike with a view of the marsh along the Mt Hope River at the site of one of Ashford’s original homesteads
  • Knowlton Hill Preserve★★— 2.5 miles — From the serene hillside of a glacial drumlin explore 2.5 miles of trails passing the Knowlton Estate and local history on a self-guided hike
  • Rankin Preserve★★— 1.5 miles — One of Joshua’s Trust’s newest trails past linked ponds to a loop through rocky ledges and sloping forest
  • Tinkerville Brook★★— 1.2 miles — A hidden gem this loop hike passes the ruins of an old bridge along a brook named for the gypsies that camped along it

State Parks / Forest

  • Natchaug State Forest (see blue blaze below)

Blue Blaze – Nipmuck and Natchaug in Ashford

  • Natchaug Trail
    • Natchaug: Lyon Rd — 8 miles — A long secluded stretch along Bigelow Brook from Eastford into Ashford until the Natchaug’s north terminus
  • Nipmuck Trail
    • Marsh Road — 2.7 miles — Rerouted in 2017 this long stretch passes the backside of a farm to meet old roads and Knowlton Brook before crossing Rt. 74
    • Natchaug State Forest: West Ashford Block — 1.2 miles — After crossing Rt. 74 enter designated “old forest” with steep slopes and dense mountain laurel
    • Natchaug State Forest: Perry Hill — 2.3 miles — Gradual terrain passes through land rebounding from a timber harvest
    • Turn right for a 0.7 mile road walk along Oakes Rd, cross Rt. 89 diagonally and head 0.2 miles down Iron Mine Ln
    • Pixie Falls — 2.1 miles — This section features old foundations, Pixie Falls, a stretch of the 400 year old Old Connecticut Path, and Ladies Room Rock
      • Camping Area just past Pixie Falls
    • Yale Forest: Eastford Road — 1.6 miles — A largely forgettable section that passes along a small ridge through alternating mountain laurel and open forest
    • Yale Forest: Boston Hollow — 4.2 miles — The most rugged stretch of the entire trail with a steep climb to a narrow vista then dense laurel, hills, and valleys
    • 0.1 mile road walk along Barlow Mill Rd
    • Yale Forest: Walker Mountain — 1.9 miles — This section heads up and up and up with a new spur trail to the Walker Mountain summit and then down through the Yale Forestry school

The Rest

  • Yale Forest (see blue blaze above)

Now go out and hike Ashford, CT!

Natchaug Trail: Lyon Rd


41.8716650, -72.0878170

Natchaug Trail – Lyon Rd Connecticut Blue Blaze Trail in Eastford, CT Parking: Shoulder parking across from the cemetery at Lyon Rd (41.8716650, -72.0878170) Trail Map    … Read more…

Iron Mine Valley


41.898831, -72.167540

Iron Mine Valley Preserve Joshua’s Trust 52 acres in Ashford, CT Parking: Shoulder parking near 31 Sand Hill Rd, Ashford, CT Trail Map      Trails: 1.3… Read more…

Fliegal Farm Woods


41.894127, -72.200063

Fliegal Farm Woods Joshua’s Trust 5 acres in Ashford, CT Parking: Shoulder parking near 98 E Howey Rd, Ashford, CT Trail Map     Trails:      Rating:… Read more…

Church Farm


41.838798, -72.171105

Church Farm Joshua’s Trust Property 79 acres in Ashford, CT Parking: Shoulder parking near 179 Varga Rd Ashford, CT for the loop and small pull off across… Read more…

Tinkerville Brook


41.927542, -72.207901

Tinkerville Brook Joshua’s Trust Preserve 42 acres in Ashford, CT Parking: Small pull-off near 135 Armitage Rd, Ashford, CT Trail Map Trails: 1.2 miles    Rating: ★★☆☆☆… Read more…

Walker Mountain


41.975883, -72.140336

Yale Forest: Walker Mountain Connecticut Blue Blaze Trail in Ashford and Union, CT Parking: North end: Shoulder parking just east of the main entrance to Bigelow Hollow… Read more…