1
Laurel Ridge
Managed by Winchester Land Trust
508 acres5.9 mi of trail
Laurel TrailRidge TrailLong Pond TrailTrotter Track TrailCharcoal Trail
Dog rules not recorded
DirectionsTo the parking lot
Outdoors · Winchester
Winchester, CT parks, trails & bike paths
About 14% of Winchester is conserved land, roughly 2,970 acres. There are about 20 miles of mapped trails, and the biggest networks are in Laurel Ridge (5.9 mi), Algonquin State Forest (2.9 mi), and Town of Winchester Watershed Lands (1.7 mi).
Conserved land, trails, parks and bike routes in Winchester, measured from OpenStreetMap and USGS data.
At a glance
Winchester outdoors
Conserved land
14%
2,970 of 21,521 acres
Trails
20 mi
0.6 mi per sq mi · 8 on conserved land
Parks & preserves
43
289 conserved acres per 1,000 residents
Bike routes
1.1 mi
0.0 mi lanes · 1.1 mi off-road paths
Conserved land is a share of the whole town area. Bike lanes are often missing from the map in smaller towns, so that number is likely low.
Map
Conserved land, trails & bike routes
Tap a number or a place below to zoom in© OpenStreetMap contributors · USGS PAD-US
Places to walk
Parks & preserves with trails
Ranked by mapped trail miles. Directions go to the nearest marked trailhead or public parking.
2
Algonquin State Forest
Managed by State of Connecticut
646 acres2.9 mi of trail
Dog rules not recorded
No trailhead mapped yet
3
Town of Winchester Watershed Lands
Managed by Town of Winchester
1,339 acres1.7 mi of trail
Old Waterbury Turnpike
Dog rules not recorded
No trailhead mapped yet
4
Houlihan Woods and Michael Giordano Tribute Area
Managed by Winchester Land Trust
49 acres1.4 mi of trail
Dog rules not recorded
DirectionsTo the parking lot
5
Burr Pond State Park
Nature preserve
191 acres1.2 mi of trail
Dog rules not recorded
DirectionsTo the parking lot
6
Mountainside Open Space
Managed by Town of Winchester
204 acres0.7 mi of trail
Dog rules not recorded
No trailhead mapped yet
7
Ruez Trail
Managed by Winchester Land Trust
27 acres0.7 mi of trail
Old Waterbury Turnpike
Dog rules not recorded
No trailhead mapped yet
8
Ehrich Woods
Managed by Winchester Land Trust
228 acres0.6 mi of trail
Old Waterbury Turnpike
Dog rules not recorded
No trailhead mapped yet
All 43 parks & preserves
- Paugnut State Forest148 ac · 0.5 mi trail
- Old Crossroad Trail2 ac · 0.2 mi trail
- Rosgen Woods60 ac · 0.1 mi trail
- Walker Field8 ac · 0.1 mi trail · Directions
- Soldiers Memorial Monument5 ac · 0.1 mi trail · Directions
- Platt Hill State Park318 ac
- Silas Hall Pond Preserve199 ac
- Julia Berger and William Treiber Refuge111 ac
- Platt Hill Preserve63 ac
- Hurlbut Field40 ac
- Camp Wahnee39 ac
- Cannavo Springs Watershed23 ac
- Tatro Pond Open Space23 ac
- Mount McNiff Preserve14 ac
- Fong Family Preserve11 ac
- Rowley Fields9 ac · Directions
- Hollow Road Preserve9 ac
- Long Point Ridge8 ac
- Highview Drive Open Space6 ac
- Carey Point6 ac
- Stevens Preserve5 ac
- State of CT5 ac
- Church Field5 ac
- Park Pond Preserve4 ac
- Reaching Hill Road Preserve4 ac
- Marshall Street Preserve4 ac
- Sucker Brook Preserve3 ac
- Locascio Preserve2 ac
- Winchester Center Playground1 ac
- Riverton Road Preserve1 ac
- Resha Beach1 ac
- Blacksmith Homestead1 ac
- Still River Preserve1 ac
- White Street Open Space1 ac
- North Main Street Open Space1 ac
Who protects the land
2,970 conserved acres
Who manages it, from PAD-US. Approximate, because parcels can overlap.
Conserved doesn't always mean open to visitors. 61 acres are conservation easements, which are usually private land. Public access isn't recorded for 58 of 65 parcels. The places listed above are parks and preserves people visit.
Biking & sports
Bike routes, courts & fields
- Painted or protected bike lanes0.0 mi
- Off-road bike paths1.1 mi
- Shoulders & shared lanes0.0 mi
Courts & fields
- Tennis8
- Baseball4
- Pickleball2
- Basketball2
- Multi-sport2
- Softball1
Counts include school and college facilities, which aren't always open to the public.
Next door
Winchester and its neighbors
Towns whose outdoors data has been built so far.
| Town | Conserved | Trails | Parks & preserves |
|---|---|---|---|
| Winchester | 13.8% | 20.3 mi | 43 |
| Torrington | 21.6% | 30.3 mi | 22 |
| Colebrook | 23.7% | 47.7 mi | 13 |
| Barkhamsted | 22.3% | 53.7 mi | 13 |
Trail talk
Conditions & tips from neighbors
No recent posts about Winchester's trails yet. Muddy, icy, a bridge out, where to park: a quick post helps the next person.
Sources: trails, parks, preserves, courts and bike lanes © OpenStreetMap contributors (ODbL), map data as of 2026-09-28. Conserved land: USGS Gap Analysis Project, Protected Areas Database of the United States (PAD-US). Measured against the Census town boundary.
How we measure
"Trails" are OpenStreetMap paths, bridleways, public tracks and unpaved footways, plus footways inside a park or preserve or on a named trail route. Sidewalks are left out. Areas are counted on a 21.7-meter grid, so overlapping parcels count once. "Conserved" includes conservation easements, which protect land from development but are usually private property. Trailheads are the nearest marked trailhead, public parking lot or information board within about 150 meters of a preserve. Dog rules come from OpenStreetMap when someone has tagged them; otherwise we show what's typical for the land manager, or say the rules aren't recorded.