Ashford

Hike Ashford, CT

(Part of Windham County)

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.

Ashford has a total of 17 hikes for 39.5 miles of trails, but unfortunately not much for fishing or boating opportunities.

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My Highlights |expand|

Hiking |expand|

Town Parks

Land Trust

  • Joshua’s 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
    • West Ashford Block – 1.2 miles – After crossing Rt. 74 enter designated “old forest” with steep slopes and dense mountain laurel
    • Perry Hill – 2.3 miles – Gradual terrain passes through land rebounding from a timber harvest
    • Pixie Falls – 2.1 miles – This section of the Nipmuck features old foundations, Pixie Falls, a stretch of the 400 year old Old Connecticut Path, and Ladies Room Rock

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
    • Eastford Road – 1.6 miles – A largely forgettable section of the Nipmuck Trail that passes along a small ridge through alternating mountain laurel and open forest
    • Boston Hollow – 4.2 miles – The most rugged stretch of the Nipmuck with a steep climb to a narrow vista then dense laurel, hills, and valleys
    • 0.1 mile road walk along Barlow Mill Rd
    • Walker Mountain – 1.9 miles – Nipmuck Trail 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

Boating/Fishing |expand|

  • Not much for boating unless you have private access but fishing
    • Mt. Hope River at Ashford Memorial Park
    • Ashford Lake

Breweries, Bakeries, and More |expand|

Town History |expand|

Ashford was first settled in 1710 and was quickly incorporated as town in October 1714 making it the 44th oldest town in Connecticut.  The name is likely named after Ashford in Kent, England.

President George Washington passed through the town on November 7th 1789 after stopping in Pomfret intending to see Israel Putnam. He involuntarily stayed the night in town when the villagers proclaimed it was against the law to travel/hire a carriage on a Sunday. Read his diary entry here.

Now go out and hike Ashford, CT!

Ashford Memorial Park

★★☆☆☆

Ashford Memorial Park, Ashford, CT, USA

Ashford Memorial Park Ashford Town Park 33 acres in Ashford, CT Parking: Medium sized lot near 1 Pompey Hollow Park Access Road, Ashford, CT Trail Map   …

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    …

Morey Pond Boat Launch

★★☆☆☆

41.970439, -72.194359

Morey Pond Boat Launch Connecticut State Water Access 44 acres in Union, CT Parking: Down the road near 723 Buckley Hwy Union, CT Trail Map     …

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:…

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: 0.3 miles …

Friedman Forest

★★☆☆☆

41.845289, -72.150130

Abraham R. and Samuel H. Friedman Memorial Forest Joshua’s Trust 143 acres in Ashford, CT Parking: Small lot near 427 Bebbington Rd Ashford, CT Trail Map   …

Church Farm

★★☆☆☆

41.838798, -72.171105

Church Farm Joshua’s Trust Property 79 acres in Ashford, CT Parking: Main Parking: Small pull off near 29 Varga Rd, Ashford, CT for blue access trail Shoulder… Read more…

Josias Byles Sanctuary

★★☆☆☆

41.868035, -72.150976

Josias Byles Sanctuary Joshua’s Trust Property 69 acres in Ashford, CT Parking: Small pull off near 111 Ashford Center Rd Ashford, CT Trail Map       Trails:…

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 …

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…