Hike Woodstock, CT

(Part of Windham County)

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

Woodstock is the second largest town in the state, encompassing 61.8 square miles (after New Milford).  There are 11 hikeable locations with a dozen miles of trails, 4 options for boating/fishing, and a handful of unique local bakeries breweries and stores.



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Town Parks

  • Crystal Pond Park –★★★– 2.5 miles – Hiking, disc golf, and water access all in one spot, though hiking trails are a bit rough
  • Fifty Acre Wood –★★– 1.5 miles – Nearly a forgotten town trail, somewhat overgrown loop
  • Muddy Pond – Woodstock Town Beach open to town residents only, no boating

Land Trust

  • New Roxbury Land Trust – None of their properties have marked trails
    • Bishop Preserve
    • Border Woods – Off Rt. 198 about 200ft of trail that dead ends quickly at private property
    • Kenyon Woods
  • Wyndham Land Trust
    • Cabbage Hill ★★– 1.5 miles – Mowed paths to a great field view and an old cemetary
    • Cartier Preserve ★★– 1.2 miles – New unblazed trail through an ocean of ferns and dense mountain laurel
    • Little River Greenway ★– 0.15 miles – Very short boardwalk with no views
    • Rapoport Preserve –★– 1.5 miles – Likely nicer in the winter, these trails are overgrown without much to note
    • Rocky Hill Refuge –★– 0.5 miles – Skip this out and back field-access road

State Parks / Forest

Blue Blaze

  • Wabbaquasset Trail –★★★– 1.3 miles – The state’s newest blue blaze trail is a picturesque loop through Hibbard Forest

The Rest

  • Lem Walker Loop at Hatchet Hill – Private property, no access
  • The Old Connecticut Path – Historical path
  • Roseland Park – Unexplored [/expand]

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  • Black Pond – 77 acre pond next to the YMCA camp
  • Crystal Pond – 148 acre pond with a developed shoreline
  • North Running Brook Fishing Hole – A couple fishing spots on either side of Joy Road
  • Roseland Lake – Fishing is considered excellent in this 90 acre state stocked lake


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  • Farm to Table Market – Great farm store with local meats, milk in glass bottles, and other local products
  • Soleil BakeryThursday-Sunday 10-6pm – Old fashioned bakery items, old world breads, and personalized cake options
  • Sweet Evalina’s Stand – A little hidden gem with fresh-prepared casual foods
  • Taylor Brook Winery and Brewery – Two separate buildings for tastings and casual hang out spots[/expand]

[expand title=”History    |expand|” tag=”h3″]

Geologically a glacial drumlin field.  The area was historically home to the Wabbaquasset tribe or band meaning “mat producing country” part of the larger Nipmuck tribe.  The Old Connecticut Path which ran from the Connecticut River to modern day Boston passed through Woodstock above Crystal and Woodstock Ponds.  At the time the settlers came, Wabbaquasset country was held by the Mohegan Uncas as a Pequot conquest.  The land was formally deeded to Captain James Fitch in 1680 and in 1686, residents from Massachusetts settled the area and called it New Roxbury.

The Puritan missionary John Eliot encouraged the Native Americans to form a village of “Praying Indians” in South Woodstock. He called it Wahbuquoshish meaning “near the bend in the outlet from Woodstock Pond.” In 1934, Arthur Basto, an amateur archeologist, confirmed that this village was located near Woodstock Pond, on the site of the William Basto Farm.

While largely agricultural in nature, “by 1820, there were 2 distilleries, 2 wheel wrights, an oil mill, fulling mill, carding machines, grist mills, saw mills, a goldsmith, and twine and cotton batting operations. Woodstock Valley was known for its shoe factories,” according to the history page at the Woodstock town site.  Industry didn’t last long, reverting to a rural town and becoming a summer destination for wealthy city dwellers.[/expand]

Now go out and hike Woodstock, CT!

Roseland Park


205 Roseland Park Rd, Woodstock, CT 06281, USA

Roseland Park Private Park 390 acres in Woodstock, CT Parking: Several lots near 205 Roseland Park Rd, Woodstock, CT Trail Map       Trails: 0.25 miles   …

Black Pond Boat Launch


215 Camp Road, Woodstock, Woodstock Valley, CT, USA

Black Pond Boat Launch Connecticut State Boat Launch 41 acres in Woodstock, CT Parking: Small lot down a driveway off Camp Road Trail Map     Trails: No…

Little River Greenway


Little River Greenway, Little Pond Road, Woodstock, CT, USA

Little River Greenway Preserve Wyndham Land Trust 55 acres in Woodstock, CT Parking: Pull off for two cars near Little Pond Rd, Woodstock, CT Trail Map    …

Cartier Preserve


41.915667, -72.022337

Cartier Preserve Wyndham Land Trust 86 acres in Woodstock, CT Parking: Shoulder parking near 161 Quarry Road Woodstock, CT Trail Map         Trails: 1 mile …

Cabbage Hill


Cabbage Hill Road, Woodstock, CT, USA

Cabbage Hill Preserve Wyndham Land Trust 112 acres in Woodstock, CT Parking: Small lot at the end of Cabbage Hill Rd Trail Map        Trails:…

Fifty Acre Wood


55 Pond Factory Road, Woodstock, CT, USA

The Fifty Acre Wood Woodstock Town Park 50 acres in Woodstock, CT Parking: Small pull-off near 55 Pond Factory Road, Woodstock, CT Trail Map       …

Wabbaquasset Trail


182 Pond Factory Rd, Woodstock, CT 06281, USA

Wabbaquasset Trail at Hibbard Forest Connecticut Blue Blaze Trail 100 acres in Woodstock, CT Parking: Small lot near 182 Pond Factory Rd, Woodstock, CT Trail Map   …

Bull Hill


198-162 Bull Hill Rd, Woodstock, CT 06281, USA

Bull Hill Project Wyndham Land Trust Property 994 acres in Woodstock and Thompson, CT Parking: Small lot uphill from 174 Bull Hill Rd Woodstock, CT Trail Map   …

Rocky Hill Refuge


41.933477, -72.032128

Rocky Hill Refuge Wyndham Land Trust 57 acres in Woodstock, CT Parking: Shoulder parking near 321 Rocky Hill Rd Woodstock, CT Trail Map        Trails:…

Rapoport Preserve


41.950421, -72.004849

Linda J. Rapoport Memorial Preserve Wyndham Land Trust 154 acres in Woodstock, CT Parking: Two options Shoulder parking near 287 Pulpit Rock Rd, Woodstock, CT Shoulder parking…