Yankee Expressway Highlands
Managed by Town of Cheshire
326 acres8.2 mi of trail
Dog rules not recorded
Directionsto the parking lot
Photo: John Phelan · CC BY-SA 3.0A−Outdoors
Outdoors in Cheshire
Cheshire has 49 miles of mapped trails, 1.5 for every square mile of land
12% of Cheshire’s land is conserved, about 2,466 acres. The biggest trail networks: Yankee Expressway Highlands (8.2 mi), DeDominicis Property (5.2 mi), Ives Farm (2.3 mi). 422 acres are parks and preserves, 15 per 1,000 residents.
Ahead of 80% of U.S. towns · #82 of 155 in Connecticut. What drives it
Conserved land
12%
2,466 acres · of 32.8 sq mi of land
Trails
49 mi
1.5 per sq mi of land
Park land
422 ac
15 acres per 1,000 residents
Near a park
67%
of residents within ½ mile
Bike routes
10 mi
7.5 mi paths
Highest peak
371 ft
Peck Mountain
Lakes & rivers
18
1 beach · 1 boat launch
What kind of outdoors town is Cheshire?
Read from the map. The page puts what stands out first.
Outdoors grade
How much outdoors does Cheshire have?
On conserved land, trails, park land and how close residents live to a park, Cheshire is ahead of 80% of U.S. towns, #82 of 155 in Connecticut. All four inputs are above most U.S. towns; trail miles rank highest, the share of residents near a park lowest.
A−
OutdoorsA character grade: shown, never part of Cheshire’s overall grade.
Conserved land12% of the land · typical CT town 15% · U.S. 4%A−Trails1.5 miles of mapped trail per square mile of land (49 mi) · CT 1.4 · U.S. 0.4APark land15 acres of park per 1,000 residents (422 acres) · CT 22 · U.S. 13BParks close to home67% of residents within a half mile of a park · CT 57% · U.S. 72%B−
All U.S. towns we grade (21,298)Ahead of 80%
LessMore
Connecticut towns of 2,500+ (155)Ahead of 47%
Connecticut towns conserve more land than most (a typical one, 15%; the U.S., 4%), so Cheshire’s 12% is ahead of 32% of Connecticut towns, while its trails per square mile lead 53% of them.
How sure. Graded on any three of the four inputs instead, the letter would range from B+ to A−. Trails and many small parks come from OpenStreetMap, mapped by volunteers, so coverage varies from town to town; the half mile is a straight line from each census block, so a river or highway in the way isn’t counted against it.
PAD-US, OpenStreetMap (© OpenStreetMap contributors), Census 2025 Gazetteer and 2020 blocks; details in Sources below. How TownRatings grades the outdoors →
The map
Conserved land, trails & bike routes
Tap a number to zoom to a park. Tap a layer to hide it.
Easements protect land from building but are usually private.© OpenStreetMap contributors · USGS PAD-US
Places to walk
Pick a walk
The longest trail network is Yankee Expressway Highlands, with 8.2 miles. Directions go to the nearest trailhead or public parking.
DeDominicis Property
Managed by Town of Cheshire
197 acres5.2 mi of trail
Dog rules not recorded
Directionsto the parking lotWebsite ↗
Ives Farm
Managed by Cheshire Land Trust
170 acres2.3 mi of trail
Dog rules not recorded
Directionsto the parking lot
Cheshire Park
Managed by Town of Cheshire
59 acres2.2 mi of trail
Dog rules not recorded
Directionsto the parking lot
Roaring Brook Park
Managed by Town of Cheshire
92 acres1.9 mi of trail
Dog rules not recorded
Directionsto the parking lot
Casertano Property
Managed by Town of Cheshire
87 acres1.9 mi of trail
blue trail
Dog rules not recorded
Directionsto the parking lot
Fresh Meadows Wildlife Sanctuary
Managed by Cheshire Land Trust
44 acres1.4 mi of trail
Dog rules not recorded
Directionsto the parking lot
Naugatuck State Forest - Mount Sanford Block
Nature preserve
171 acres1.2 mi of trail
Dogs allowed
Directionsto the parking lot
All 53 parks & preserves
Yankee Expressway Highlands326 acres · 8.2 mi of trail · Town of Cheshire
DirectionsDeDominicis Property197 acres · 5.2 mi of trail · Town of Cheshire
DirectionsIves Farm170 acres · 2.3 mi of trail · Cheshire Land Trust
DirectionsCheshire Park59 acres · 2.2 mi of trail · Town of Cheshire
DirectionsRoaring Brook Park92 acres · 1.9 mi of trail · Town of Cheshire
DirectionsCasertano Property87 acres · 1.9 mi of trail · Town of Cheshire
DirectionsFresh Meadows Wildlife Sanctuary44 acres · 1.4 mi of trail · Cheshire Land Trust
DirectionsNaugatuck State Forest - Mount Sanford Block171 acres · 1.2 mi of trail
DirectionsBrooke Preserve39 acres · 1.2 mi of trail · Cheshire Land Trust
DirectionsMixville Park63 acres · 1.1 mi of trail · Town of Cheshire
DirectionsBartlem Park59 acres · 1.1 mi of trail
DirectionsRiverbound Farm Sanctuary25 acres · 1.1 mi of trail · Quinnipiac Valley Audubon Society
DirectionsBoulder Knoll Property189 acres · 0.8 mi of trail · Town of Cheshire
Puchalski Property120 acres · 0.7 mi of trail · Town of Cheshire
Ten Mile Lowlands Property158 acres · 0.6 mi of trail · Town of Cheshire
DirectionsBen's Homestead40 acres · 0.5 mi of trail · Town of Cheshire
Mixville Hills Property81 acres · 0.3 mi of trail · Town of Cheshire
Russell Family Memorial36 acres · 0.2 mi of trail · Cheshire Land Trust
DirectionsBrooksvale Park4 acres · 0.2 mi of trail
DirectionsFarmington Canal Line State Park Trail73 acres · 0.1 mi of trail
DirectionsQuinnipiac Recreation Area23 acres · 0.1 mi of trail
DirectionsLock 12 Historical Park14 acres · 0.1 mi of trail · Town of Cheshire
DirectionsNaugatuck State Forest171 acres · Connecticut Department of Energy and Environmental Protection
Thomas Pool Memorial25 acres · Cheshire Land Trust
Subdivision Open Space (Southwood Rd) 2 Parcels18 acres
Copper Valley Club15 acres
Judd Brook Preserve15 acres · Cheshire Land Trust
Briar Court & Salvadore Memorial Preserves13 acres · Cheshire Land Trust
Ten Mile River Preserve12 acres · Cheshire Land Trust
West Cheshire Highlands11 acres · Cheshire Land Trust
Sharon Drive Preserve11 acres · Cheshire Land Trust
DirectionsWillow Brook Preserve10 acres · Cheshire Land Trust
DirectionsMcNamara Field10 acres
DirectionsCarmichael Sanctuary-Nettleton's Ravine9 acres · Cheshire Land Trust
Town Open Space (Contour Drive)8 acres
Brooksvale Preserve7 acres · Cheshire Land Trust
Cran Preserve7 acres · Cheshire Land Trust
Strathmore Preserve7 acres · Cheshire Land Trust
Old Farms Preserve6 acres · Cheshire Land Trust
DirectionsJosephine's Woods Preserve6 acres · Cheshire Land Trust
Sylvan Lane Preserve6 acres · Cheshire Land Trust
Town Open Space (Gaylord F. & Shoebox)5 acres
Carroll Woods5 acres · Cheshire Land Trust
Woodhaven Preserve5 acres · Cheshire Land Trust
Kolstad Woods4 acres · Cheshire Land Trust
Inverness Glen4 acres · Cheshire Land Trust
Doede Estate Preserve3 acres · Cheshire Land Trust
Seeley Acres3 acres · Cheshire Land Trust
Tow Path Acres2 acres · Cheshire Land Trust
DirectionsTown Open Space (Cedar Lane)2 acres
Town Open Space (Mansion Road)1 acres
DirectionsThe Church Green1 acres
DirectionsGateway Park1 acres
Who protects it
2,466 conserved acres
12% of Cheshire’s land. Who manages Cheshire’s conserved land, from the USGS Protected Areas Database. Approximate, because parcels can overlap.
State conservation270 ac
Other state land93 ac
Land trusts & nonprofits46 ac
Town or city40 ac
Not recorded2,289 ac
Local Other or Unknown · 1,103 acPrivate Conservation · 745 acUnknown Easement · 276 acState Resource Management Area · 172 acLocal Park · 160 ac
Good to know
Conserved doesn’t always mean open to visitors. 97 acres are conservation easements, usually private land. Public access isn’t recorded for 137 of 143 parcels. The walks above are places people visit.
The biggest protected parcels
| Parcel (PAD-US) | Managed by | Acres | Public access |
|---|---|---|---|
| Unknown Private Conservation | Not recorded | 1,825 | Unknown |
| Naugatuck State Forest State Resource Management Area | Not recorded | 178 | Unknown |
| Farmington Canal Line State Park Trail State Park | Not recorded | 78 | Unknown |
| Mixville Park Local Park | Not recorded | 62 | Unknown |
| Prospect Ridge Greenbelt State Other or Unknown | Not recorded | 45 | Unknown |
| Roaring Brook Park Local Park | Not recorded | 39 | Unknown |
| Cross Rocks Farm Local Other or Unknown | Not recorded | 37 | Unknown |
| Cheshire Land Trust. Inc. (Helen Russell Memorial) Local Conservation Area | Land trusts & nonprofits | 37 | Open |
| Bartlem Recreation Area Local Park | Town or city | 34 | Open |
| Lock 12 Historic Park Local Park | Not recorded | 14 | Unknown |
5 smaller protected places aren’t shown.
Things to do
20 places to go in Cheshire
Beaches, playgrounds, peaks, falls and more. Pick a kind.
Beaches in Cheshire
1 beach without a name on the map. Tap “Show all on map” to see it.
Playgrounds in Cheshire
12 playgrounds without a name on the map. Tap “Show all on map” to see them.
Boat launches in Cheshire
Quinnipiac River Public Access
DirectionsWaterfalls in Cheshire
Roaring Brook FallsIn Roaring Brook Park
DirectionsPlus 1 waterfall without a name on the map.
Scenic views in Cheshire
2 scenic views without a name on the map.
Peaks in Cheshire
Peck Mountain371 ft elevation
DirectionsJinny Hill312 ft elevation
DirectionsTrails & water
1 named trail and 18 lakes & rivers
Named trails
Unpaved · 16.5 mi
blue trail0.5 mi
Lakes & rivers tap for directions
Broad Brook ReservoirreservoirCheshire Park PondpondCook Hill PondCuff Brook PondpondEast Mixville PondpondHicock PondpondHoneypot Brook PondLarsens PondpondMoss Farms PondreservoirMount Sanford Road PondpondMystic ReservoirreservoirRavenswood DamreservoirShapiro PondWeeks PondlakeWest Mixville PondpondMill RiverQuinnipiac RiverTenmile River
Biking & sports
10 miles of bike routes
Bike lanes are often missing from the map in smaller towns, so that number is likely low.
7.5 mi
off-road bike paths
2.7 mi
shoulders & shared lanes
Courts & fields
32Tennis
20Baseball
15Basketball
10Soccer
4Football
4Pickleball
1Softball
1Beach volleyball
Includes school and college facilities, which aren’t always open to the public.
History along the way
History →3 places on the National Register
The country’s official list of places worth saving (National Park Service). The map also marks 1 historic points from OpenStreetMap: plaques, memorials and old buildings.
When to get out
The best walking months in Cheshire: April to September
NOAA’s 1991–2020 normals for the town and the daylight at its latitude. Outlined months have long days, highs of 59 to 86 °F and little rain for the place.
| Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Daylight (h) | 9.5 | 10.5 | 11.8 | 13.3 | 14.5 | 15.2 | 14.9 | 13.8 | 12.4 | 11.0 | 9.8 | 9.2 |
| High (°F) | 37 | 39 | 48 | 60 | 70 | 79 | 84 | 82 | 75 | 63 | 52 | 41 |
| Rain (in) | 3.7 | 3.3 | 4.2 | 4.3 | 3.7 | 4.4 | 4.1 | 4.0 | 4.5 | 4.8 | 4.0 | 4.3 |
February is the driest month (3.3 in) and July the warmest (highs of 84 °F). 4.8 inches fall in October, the wettest month. The climate in Cheshire →
Next door
Cheshire and its neighbors
Tap a town to see its outdoors.
Hamden123 miSouthington69 miWallingford59 miCheshire49 miMeriden44 miWaterbury25 miWolcott20 miProspect12 mi
| Town | Conserved of land | Trail mi per sq mi | Park acres per 1,000 | Near a park ½ mile | Outdoors |
|---|---|---|---|---|---|
| Cheshire | 12% | 1.5 | 15 | 67% | A− |
| Prospect | 3% | 0.9 | 17 | 38% | B |
| Southington | 9% | 1.9 | 11 | 36% | B+ |
| Meriden | 14% | 1.9 | 28 | 87% | A |
| Wallingford | 15% | 1.5 | 56 | 82% | A |
| Waterbury | 5% | 0.9 | 5 | 83% | B |
| Hamden | 16% | 3.8 | 13 | 49% | A− |
| Wolcott | 2% | 1.0 | 5 | 30% | C+ |
The four inputs of the Outdoors grade, from the engine; shares are of land, not water.
Questions about parks and trails in Cheshire
Where can I hike in Cheshire?
The longest trail networks: Yankee Expressway Highlands, 8.2 miles; DeDominicis Property, 5.2 miles; Ives Farm, 2.3 miles; Cheshire Park, 2.2 miles. Each one is on the map above, with directions to the nearest trailhead or parking.
How much of Cheshire is conserved land?
12% of its land, against a typical 15% for a Connecticut town and 4% nationally (PAD-US). Conserved doesn’t always mean open to visitors: easements are usually private land.
Are dogs allowed on Cheshire’s trails?
OpenStreetMap records dogs as welcome at Naugatuck State Forest - Mount Sanford Block. For the rest, check the signs at the trailhead.
Where can I bike in Cheshire?
10 miles of bike routes are on the map: 7.5 of off-road paths and 2.7 of shoulders and shared lanes.
Is there public land near Cheshire?
15,333 acres of parks and open public land lie inside Cheshire or within 10 miles of it (PAD-US), 422 of them inside the town line.
How much outdoors does Cheshire have?
Ahead of 80% of U.S. towns on the Outdoors grade, #82 of 155 in Connecticut. The grade combines the share of land that is conserved, miles of mapped trail per square mile of land, park acres per 1,000 residents and the share of residents within a half mile of a park. It’s a character grade, so it isn’t part of the overall grade. How it works.
Trail talk
Conditions, parking and favorite walks from Cheshire neighbors.
Share a tip
Sources
Where this page comes from
Conserved and public land: USGS Protected Areas Database of the United States (PAD-US), service updated July 2026. Parks, trails, playgrounds, beaches and other places: OpenStreetMap (© OpenStreetMap contributors, ODbL), map data as of 2026-10-28. Land and water area: Census 2025 Gazetteer. Residents near a park: 2020 Census blocks. National Register: National Park Service. How TownRatings grades the outdoors →