Whittemore Sanctuary
Managed by Flanders Nature Center
702 acres8.5 mi of trail
Dog rules not recorded
Directionsto the parking lot
Photo: Ramiska · CC BY-SA 4.0A−Outdoors
Outdoors in Woodbury
20% of Woodbury’s land is conserved: 4,541 acres
38 miles of mapped trail cross Woodbury, 1.1 per square mile of land. 471 acres are parks and preserves, 48 per 1,000 residents. The biggest trail networks: Whittemore Sanctuary (8.5 mi), Trolley Bed Preserve (6.1 mi), Van Vleck Farm and Nature Sanctuary (5.5 mi).
Ahead of 83% of U.S. towns · #69 of 155 in Connecticut. What drives it
Conserved land
20%
4,541 acres · of 36.4 sq mi of land
Trails
38 mi
1.1 per sq mi of land
Park land
471 ac
48 acres per 1,000 residents
Near a park
43%
of residents within ½ mile
Highest peak
925 ft
Blackmans Hill
Lakes & rivers
24
1 beach
What kind of outdoors town is Woodbury?
Read from the map. The page puts what stands out first.
Outdoors grade
How much outdoors does Woodbury have?
On conserved land, trails, park land and how close residents live to a park, Woodbury is ahead of 83% of U.S. towns, #69 of 155 in Connecticut. Conserved land holds the grade up; the share of residents near a park pulls it down.
A−
OutdoorsA character grade: shown, never part of Woodbury’s overall grade.
Conserved land20% of the land · typical CT town 15% · U.S. 4%ATrails1.1 miles of mapped trail per square mile of land (38 mi) · CT 1.4 · U.S. 0.4A−Park land48 acres of park per 1,000 residents (471 acres) · CT 22 · U.S. 13A−Parks close to home43% of residents within a half mile of a park · CT 57% · U.S. 72%C+
All U.S. towns we grade (21,298)Ahead of 83%
LessMore
Connecticut towns of 2,500+ (155)Ahead of 56%
Connecticut towns conserve more land than most (a typical one, 15%; the U.S., 4%), so Woodbury’s 20% is ahead of 66% of Connecticut towns, while its trails per square mile lead 35% of them.
How sure. Graded on any three of the four inputs instead, the letter would range from A− 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 Whittemore Sanctuary, with 8.5 miles. Directions go to the nearest trailhead or public parking.
Trolley Bed Preserve
Managed by Town of Woodbury
248 acres6.1 mi of trail
Trolly Bed Preserve Trailred trail
Dog rules not recorded
Directionsto the parking lot
Van Vleck Farm and Nature Sanctuary
Managed by Flanders Nature Center
187 acres5.5 mi of trail
Dog rules not recorded
Directionsto the parking lot
Orenaug Park
Managed by Town of Woodbury
86 acres2.1 mi of trail
Tower Trail
Dog rules not recorded
Directionsto the parking lot
Leavenworth Preserve
Managed by Flanders Nature Center
110 acres1.7 mi of trail
Dog rules not recorded
Directionsto the trail sign
Good Hill Farm Preserve
Managed by Roxbury Land Trust
126 acres1.2 mi of trail
Dog rules not recorded
Directionsto the parking lot
Miller Preserve Addition
Managed by Roxbury Land Trust
117 acres1 mi of trail
Dog rules not recorded
Directionsto the parking lot
Three Rivers Park
Park
73 acres0.9 mi of trail
Three Rivers Park Walking PathThree Rivers
Dog rules not recorded
Directionsto the parking lot
All 57 parks & preserves
Whittemore Sanctuary702 acres · 8.5 mi of trail · Flanders Nature Center
DirectionsTrolley Bed Preserve248 acres · 6.1 mi of trail · Town of Woodbury
DirectionsVan Vleck Farm and Nature Sanctuary187 acres · 5.5 mi of trail · Flanders Nature Center
DirectionsOrenaug Park86 acres · 2.1 mi of trail · Town of Woodbury
DirectionsLeavenworth Preserve110 acres · 1.7 mi of trail · Flanders Nature Center
DirectionsGood Hill Farm Preserve126 acres · 1.2 mi of trail · Roxbury Land Trust
DirectionsMiller Preserve Addition117 acres · 1 mi of trail · Roxbury Land Trust
DirectionsThree Rivers Park73 acres · 0.9 mi of trail
DirectionsFleming Preserve29 acres · 0.8 mi of trail · Flanders Nature Center
DirectionsHollow Park73 acres · 0.7 mi of trail
DirectionsJanie Pierce Park46 acres · 0.7 mi of trail · Town of Southbury
DirectionsHogpen Hill Farms230 acres · 0.6 mi of trail
Minortown Road Preserve23 acres · 0.4 mi of trail · Town of Woodbury
Shuttleworth Lower11 acres · 0.4 mi of trail · Flanders Nature Center
Marzahl Refuge46 acres · 0.3 mi of trail · Flanders Nature Center
DirectionsManville Kettle Property6 acres · 0.3 mi of trail · Flanders Nature Center
DirectionsMiller Preserve5 acres · 0.2 mi of trail · Roxbury Land Trust
Marra Scuppo Hill12 acres · 0.1 mi of trail · Flanders Nature Center
Baldrige Farm144 acres · Flanders Nature Center
Grey Fox Woods106 acres · Flanders Nature Center
Parker/Hart Refuge102 acres · Flanders Nature Center
Aisley Meadows64 acres · Flanders Nature Center
Skinner60 acres · Flanders Nature Center
Owl Ridge53 acres · Flanders Nature Center
Ledgewood43 acres · Flanders Nature Center
Tomlinson North38 acres · Flanders Nature Center
Church Hill B36 acres · Flanders Nature Center
Strong Meadow Preserve34 acres · Town of Woodbury
DirectionsRollingwood32 acres · Flanders Nature Center
Carriage Hills32 acres · Flanders Nature Center
Oak Meadow27 acres · Flanders Nature Center
Old Farm27 acres · Flanders Nature Center
Cox25 acres · Flanders Nature Center
Feiderowicz Refuge21 acres · Flanders Nature Center
Tomlinson South19 acres · Flanders Nature Center
Riverbend Durfee16 acres · Flanders Nature Center
Picton16 acres · Flanders Nature Center
Hillside Farm Preserve12 acres · Steep Rock Association
Applegate Acres12 acres · Flanders Nature Center
The Crossings11 acres · Flanders Nature Center
Old Town Heights11 acres · Flanders Nature Center
Finch11 acres · Flanders Nature Center
Taylor11 acres · Flanders Nature Center
Shuttleworth Upper10 acres · Flanders Nature Center
Transylvania Woods9 acres · Flanders Nature Center
Mayflower8 acres · Flanders Nature Center
Curtiss Hill8 acres · Flanders Nature Center
Town Of Woodbury Open Space8 acres
DirectionsCurtiss Woods8 acres · Flanders Nature Center
Whittemore Cottages7 acres · Flanders Nature Center
DirectionsButternut Falls7 acres · Flanders Nature Center
Riverbend6 acres · Flanders Nature Center
Good Hill Farms5 acres · Flanders Nature Center
Laurel Wood5 acres · Flanders Nature Center
Van Vleck Woodlot5 acres · Flanders Nature Center
Church Hill Woods2 acres · Flanders Nature Center
Woodbury North Green1 acres
DirectionsWho protects it
4,541 conserved acres
20% of Woodbury’s land. Who manages Woodbury’s conserved land, from the USGS Protected Areas Database. Approximate, because parcels can overlap.
Land trusts & nonprofits974 ac
Private owners759 ac
USDA easements (NRCS)339 ac
Other state land269 ac
State conservation248 ac
Town or city226 ac
Other or Unknown Local Government79 ac
Private Conservation · 1,855 acUnknown Easement · 1,521 acLocal Other or Unknown · 669 acAgricultural Easement · 564 acConservation Easement · 555 ac
Good to know
Conserved doesn’t always mean open to visitors. 1,179 acres are conservation easements, usually private land. Public access isn’t recorded for 190 of 218 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 | 2,015 | Unknown |
| Roxbury Land Trust, Inc. 19 Private Conservation | Land trusts & nonprofits | 126 | Closed |
| Flanders Woods Open Space Lot 1 Private Conservation | Not recorded | 113 | Unknown |
| Grey Fox Woods Local Conservation Area | Not recorded | 106 | Unknown |
| Orenaug Park Local Park | Not recorded | 79 | Unknown |
| Three Rivers Park Local Park | Town or city | 74 | Open |
| Flanders Nature Center and Land Trust, Inc. 29 Private Conservation | Land trusts & nonprofits | 72 | Closed |
| Aisling Meadows Local Conservation Area | Not recorded | 64 | Unknown |
| Ledgewood Estates Private Conservation | Not recorded | 53 | Unknown |
| Woods Wood Subdivision Private Conservation | Not recorded | 42 | Unknown |
5 smaller protected places aren’t shown.
Things to do
32 places to go in Woodbury
Beaches, playgrounds, peaks, falls and more. Pick a kind.
Beaches in Woodbury
1 beach without a name on the map. Tap “Show all on map” to see it.
Playgrounds in Woodbury
3 playgrounds without a name on the map. Tap “Show all on map” to see them.
Waterfalls in Woodbury
East Meadow Brook FallsIn Butternut Falls
DirectionsNonnewaug Falls
DirectionsPlus 2 waterfalls without a name on the map.
Scenic views in Woodbury
6 scenic views without a name on the map.
Peaks in Woodbury
Blackmans Hill925 ft elevation · In Whittemore Sanctuary
DirectionsHoop Pole Hill866 ft elevation
DirectionsGrassy Hill840 ft elevation
DirectionsDavidson Hill784 ft elevation
DirectionsChurch Hill781 ft elevation
DirectionsBrushy Hill705 ft elevation
DirectionsRail Tree Hill705 ft elevation
DirectionsCaleb Hill686 ft elevation · In Cox
Directions10 more peaks
Sawpit Hill682 ft elevation
DirectionsJoshua Hill646 ft elevation
DirectionsKavanaugh Hill627 ft elevation
DirectionsHogpen Hill623 ft elevation · In Leavenworth Preserve
DirectionsSherman Hill604 ft elevation
DirectionsBear Hill600 ft elevation
DirectionsPeacock Hill525 ft elevation
DirectionsOrenaug Hills509 ft elevation · In Orenaug Park
DirectionsScuppo Hill499 ft elevation
DirectionsOrenaug Rocks433 ft elevation · In Orenaug Park
DirectionsTrails & water
5 named trails and 24 lakes & rivers
Named trails
Open to bikes · 1.9 miHorses · 1.9 miUnpaved · 8.7 mi
Trolly Bed Preserve Trail1.8 mi
Three Rivers Park Walking Path0.6 mi
Tower Trail0.4 mi
red trail0.3 mi
Three Rivers0.3 mi
Lakes & rivers tap for directions
Bacon PondreservoirBlair PondpondBotany PondpondCat Swamp PondCharles Stockwell DamClarks PondCrystal LakeEngleke PondreservoirFlanders Wildlife Center PondHesseky Meadow PondJudd Hill PondKelley PondreservoirParkins Pond LowerParkins Pond UpperRadey PondReichenback PondRicker PondTransylvania PondreservoirWoodbury ReservoirWoodbury Water Co Reservoir No 1Nonnewaug RiverPomperaug RiverSprain BrookWeekeepeemee River
Biking & sports
0.0 miles of bike routes
Bike lanes are often missing from the map in smaller towns, so that number is likely low.
Courts & fields
8Soccer
6Baseball
5Tracks
4Tennis
3Basketball
3Softball
3Field hockey
2Football
Includes school and college facilities, which aren’t always open to the public.
History along the way
History →8 places on the National Register
The country’s official list of places worth saving (National Park Service). The map also marks 2 historic points from OpenStreetMap: plaques, memorials and old buildings.
Glebe HouseBuilding · listed 1971
About itWoodbury Historic District No. 1District · listed 1971
About itJabez Bacon HouseBuilding · listed 1971
About itWoodbury Historic District No. 2District · listed 1972
About itHotchkissville Historic DistrictDistrict · listed 1996
About itMinortown Road BridgeStructure · listed 2001
About itDavid Sherman HouseBuilding · listed 2002
About itLeroy Anderson HouseBuilding · listed 2012
About itWhen to get out
The best walking months in Woodbury: 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) | 35 | 38 | 47 | 59 | 70 | 78 | 83 | 81 | 74 | 62 | 50 | 40 |
| Rain (in) | 3.4 | 3.0 | 4.0 | 4.1 | 3.9 | 4.4 | 4.3 | 4.3 | 4.5 | 4.8 | 3.9 | 4.2 |
February is the driest month (3.0 in) and July the warmest (highs of 83 °F). 4.8 inches fall in October, the wettest month. The climate in Woodbury →
Next door
Woodbury and its neighbors
Tap a town to see its outdoors.
| Town | Conserved of land | Trail mi per sq mi | Park acres per 1,000 | Near a park ½ mile | Outdoors |
|---|---|---|---|---|---|
| Woodbury | 20% | 1.1 | 48 | 43% | A− |
| Middlebury | 19% | 1.3 | 84 | 73% | A |
| Bethlehem | 14% | 0.3 | 56 | 36% | B+ |
| Roxbury | 21% | 1.5 | 115 | 38% | A |
| Southbury | 17% | 1.2 | 87 | 60% | A |
| Watertown | 18% | 1.2 | 44 | 50% | A |
| Washington | 30% | 1.7 | 638 | 44% | A |
The four inputs of the Outdoors grade, from the engine; shares are of land, not water.
Questions about parks and trails in Woodbury
Where can I hike in Woodbury?
The longest trail networks: Whittemore Sanctuary, 8.5 miles; Trolley Bed Preserve, 6.1 miles; Van Vleck Farm and Nature Sanctuary, 5.5 miles; Orenaug Park, 2.1 miles. Each one is on the map above, with directions to the nearest trailhead or parking.
How much of Woodbury is conserved land?
20% 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 Woodbury’s trails?
Whittemore Sanctuary and Trolley Bed Preserve don’t have dog rules recorded on the map; check the signs at the trailhead.
Is there public land near Woodbury?
11,779 acres of parks and open public land lie inside Woodbury or within 10 miles of it (PAD-US), 472 of them inside the town line.
How much outdoors does Woodbury have?
Ahead of 83% of U.S. towns on the Outdoors grade, #69 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 Woodbury 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 →