1
Yankee Expressway Highlands
Managed by Town of Cheshire
326 acres8.2 mi of trail
Dog rules not recorded
DirectionsTo the parking lot
Outdoors · Cheshire
Cheshire, CT parks, trails & bike paths
About 12% of Cheshire is conserved land, roughly 2,466 acres. There are about 48 miles of mapped trails, and the biggest networks are in Yankee Expressway Highlands (8.2 mi), DeDominicis Property (5.2 mi), and Ives Farm (2.3 mi).
Conserved land, trails, parks and bike routes in Cheshire, measured from OpenStreetMap and USGS data.
At a glance
Cheshire outdoors
Conserved land
12%
2,466 of 21,205 acres
Trails
48 mi
1.4 mi per sq mi · 27 on conserved land
Parks & preserves
53
85 conserved acres per 1,000 residents
Bike routes
10.2 mi
0.0 mi lanes · 7.5 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
DeDominicis Property
Managed by Town of Cheshire
197 acres5.2 mi of trail
Dog rules not recorded
3
Ives Farm
Managed by Cheshire Land Trust
170 acres2.3 mi of trail
Dog rules not recorded
DirectionsTo the parking lot
4
Cheshire Park
Managed by Town of Cheshire
59 acres2.2 mi of trail
Dog rules not recorded
DirectionsTo the parking lot
5
Casertano Property
Managed by Town of Cheshire
87 acres1.9 mi of trail
blue trail
Dog rules not recorded
DirectionsTo the parking lot
6
Roaring Brook Park
Managed by Town of Cheshire
92 acres1.8 mi of trail
Dog rules not recorded
DirectionsTo the parking lot
7
Fresh Meadows Wildlife Sanctuary
Managed by Cheshire Land Trust
44 acres1.4 mi of trail
Dog rules not recorded
DirectionsTo the parking lot
8
Naugatuck State Forest - Mount Sanford Block
Nature preserve
171 acres1.2 mi of trail
Dogs allowedMapped in OpenStreetMap
DirectionsTo the parking lot
All 53 parks & preserves
Showing 1–10 of 53 parks & preserves
Yankee Expressway Highlands326 acres · 8.2 mi of trail · Town of Cheshire
DeDominicis Property197 acres · 5.2 mi of trail · Town of Cheshire
Ives Farm170 acres · 2.3 mi of trail · Cheshire Land Trust
Cheshire Park59 acres · 2.2 mi of trail · Town of Cheshire
Casertano Property87 acres · 1.9 mi of trail · Town of Cheshire
Roaring Brook Park92 acres · 1.8 mi of trail · Town of Cheshire
Fresh Meadows Wildlife Sanctuary44 acres · 1.4 mi of trail · Cheshire Land Trust
Naugatuck State Forest - Mount Sanford Block171 acres · 1.2 mi of trail
Brooke Preserve39 acres · 1.2 mi of trail · Cheshire Land Trust
Mixville Park63 acres · 1.1 mi of trail · Town of Cheshire
Who protects the land
2,466 conserved acres
Who manages it, from PAD-US. Approximate, because parcels can overlap.
Conserved doesn't always mean open to visitors. 97 acres are conservation easements, which are usually private land. Public access isn't recorded for 137 of 143 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 paths7.5 mi
- Shoulders & shared lanes2.7 mi
Courts & fields
- Tennis32
- Baseball20
- Basketball15
- Soccer10
- Football4
- Pickleball4
- Softball1
Counts include school and college facilities, which aren't always open to the public.
Nearby
Cheshire and its neighbors
Towns whose outdoors data has been built so far.
| Town | Conserved | Trails | Parks & preserves |
|---|---|---|---|
| Cheshire | 11.6% | 47.7 mi | 53 |
| Prospect | 3.1% | 12.1 mi | 14 |
| Southington | 8.6% | 69.0 mi | 16 |
| Meriden | 14% | 44.2 mi | 29 |
| Wallingford | 14.5% | 53.9 mi | 45 |
| Waterbury | 5.3% | 24.8 mi | 30 |
| Hamden | 15.4% | 123.1 mi | 31 |
Trail talk
Conditions & tips from neighbors
No recent posts about Cheshire'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 22.9-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.