Town Forest
Nature preserve
242 acres6.7 mi of trail
Burial By-passHolliston HighwayMilford BywayKrusher+1
Dog rules not recorded
Directionsto the parking lot
Photo: Smc6287 at English Wikipedia · Public domainA+Outdoors
Outdoors in Holliston
Holliston has 48 miles of mapped trails, 2.6 for every square mile of land
24% of Holliston’s land is conserved, about 2,836 acres. 1,815 acres are parks and preserves, 120 per 1,000 residents. 98% of residents live within a half mile of a park.
Among the top 1% of U.S. towns · #58 of 283 in Massachusetts. What drives it
Conserved land
24%
2,836 acres · of 18.7 sq mi of land
Trails
48 mi
2.6 per sq mi of land
Park land
1,815 ac
120 acres per 1,000 residents
Near a park
98%
of residents within ½ mile
Bike routes
6.9 mi
6.7 mi paths
Highest peak
433 ft
Bald Hill
Lakes & rivers
6
2 beaches · 2 boat launches
What kind of outdoors town is Holliston?
Read from the map. The page puts what stands out first.
Outdoors grade
How much outdoors does Holliston have?
On conserved land, trails, park land and how close residents live to a park, Holliston is among the top 1% of U.S. towns, #58 of 283 in Massachusetts. 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 Holliston’s overall grade.
Conserved land24% of the land · typical MA town 21% · U.S. 4%ATrails2.6 miles of mapped trail per square mile of land (48 mi) · MA 1.9 · U.S. 0.4A+Park land120 acres of park per 1,000 residents (1,815 acres) · MA 91 · U.S. 13AParks close to home98% of residents within a half mile of a park · MA 93% · U.S. 72%A−
All U.S. towns we grade (21,298)Among the top 1%
LessMore
Massachusetts towns of 2,500+ (283)Ahead of 80%
Massachusetts towns conserve more land than most (a typical one, 21%; the U.S., 4%), so Holliston’s 24% is ahead of 59% of Massachusetts towns, while its trails per square mile lead 66% of them.
How sure. Graded on any three of the four inputs instead, the letter would still be 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 Town Forest, with 6.7 miles. Directions go to the nearest trailhead or public parking.
Fairbanks Land
Nature preserve
204 acres5.2 mi of trail
The Main TrailKnee JerkSwamp BypassThree Sisters+1
Dog rules not recorded
No trailhead mapped yet
Wenakeening Woods
Nature preserve
106 acres3.2 mi of trail
Yellow
Dog rules not recorded
Directionsto the parking lot
Adams Street Conservation Land
Nature preserve
70 acres1.4 mi of trail
Right Turn ClydeNew TrailWhite TrailBumble Bee+1
Dog rules not recorded
Directionsto the parking lot
Rocky Woods
Nature preserve
58 acres1.2 mi of trail
The IntroCollege Rock RunIt Wasn't MeCliffwalk+1
Dog rules not recorded
No trailhead mapped yet
Poitras Memorial Land
Nature preserve
41 acres1 mi of trail
White Trail
Dog rules not recorded
No trailhead mapped yet
Brentwood Conservation Land
Nature preserve
299 acres0.9 mi of trail
Dog rules not recorded
Directionsto the parking lot
Mellen Street Conservation Area
Nature preserve
28 acres0.7 mi of trail
Blue TrailYellow Trail
Dog rules not recorded
Directionsto the parking lot
All 24 parks & preserves
Town Forest242 acres · 6.7 mi of trail
DirectionsFairbanks Land204 acres · 5.2 mi of trail
Wenakeening Woods106 acres · 3.2 mi of trail
DirectionsAdams Street Conservation Land70 acres · 1.4 mi of trail
DirectionsRocky Woods58 acres · 1.2 mi of trail
Poitras Memorial Land41 acres · 1 mi of trail
Brentwood Conservation Land299 acres · 0.9 mi of trail
DirectionsMellen Street Conservation Area28 acres · 0.7 mi of trail
DirectionsWaseeka Wildlife Sanctuary167 acres · 0.6 mi of trail · Mass Audubon
DirectionsPatoma Park30 acres · 0.5 mi of trail
DirectionsThe Daniels Property20 acres · 0.5 mi of trail
DirectionsStoddard Park13 acres · 0.2 mi of trail
DirectionsDopping Brook Wetlands77 acres
Cedar Swamp75 acres
Hamilton/Crocker Memorial26 acres
Willow Gate Rise22 acres
Strawberry Hill8 acres
Weston Pond Recreation Area8 acres
DirectionsJoseph Cohen Conservation Land7 acres
Goodwill Park5 acres
Stratton Woods5 acres
Littlefield Parcel4 acres
Linden Pond Area2 acres
Shaw Farm1 acres
Who protects it
2,836 conserved acres
24% of Holliston’s land. Who manages Holliston’s conserved land, from the USGS Protected Areas Database. Approximate, because parcels can overlap.
Town or city1,334 ac
Land trusts & nonprofits1,195 ac
Other state land330 ac
Army Corps of Engineers97 ac
Not recorded1,273 ac
Conservation Easement · 1,131 acLocal Conservation Area · 928 acLocal Other or Unknown · 845 acUnknown Easement · 365 acAgricultural Easement · 322 ac
Good to know
Conserved doesn’t always mean open to visitors. 840 acres are conservation easements, usually private land. Public access isn’t recorded for 46 of 185 parcels. The walks above are places people visit.
The biggest protected parcels
| Parcel (PAD-US) | Managed by | Acres | Public access |
|---|---|---|---|
| Unknown Park Local Conservation Area | Town or city | 448 | Open |
| Town of Holliston Local Other or Unknown | Not recorded | 336 | Open |
| Brentwood Conservation Land Local Conservation Area | Town or city | 299 | Open |
| Fairbanks Land Local Conservation Area | Town or city | 209 | Open |
| Pinecrest Golf Course Local Other or Unknown | Not recorded | 183 | Restricted |
| Waseeka Wildlife Sanctuary Private Conservation | Not recorded | 168 | Open |
| Bullard Memorial Farm Private Historic or Cultural | Not recorded | 146 | Restricted |
| Town Forest Local Resource Management Area | Not recorded | 103 | Open |
| Rocky Woods Local Other or Unknown | Town or city | 59 | Open |
| Poitras Memorial Land Local Other or Unknown | Town or city | 40 | Open |
5 smaller protected places aren’t shown.
Things to do
22 places to go in Holliston
Beaches, playgrounds, peaks, falls and more. Pick a kind.
Beaches in Holliston
Pleasure Point
DirectionsStoddard Park
DirectionsPlaygrounds in Holliston
8 playgrounds without a name on the map. Tap “Show all on map” to see them.
Boat launches in Holliston
Lake Winthrop Shorefishing AreaIn Stoddard Park
DirectionsPlus 1 boat launch without a name on the map. Tap “Show all on map” to see it.
Scenic views in Holliston
2 scenic views without a name on the map.
Peaks in Holliston
Bald Hill433 ft elevation
DirectionsMiller Hill423 ft elevation
DirectionsBroad Hill407 ft elevation
DirectionsLong Hill371 ft elevation
DirectionsStrawberry Hill269 ft elevation · In Patoma Park
DirectionsNob Hill240 ft elevation
DirectionsMount Hollis197 ft elevation
DirectionsCampgrounds in Holliston
"The Sandpits" Private Hiking and Winter Sports AreaIn Brentwood Conservation Land
DirectionsTrails & water
25 named trails and 6 lakes & rivers
Named trails
Open to bikes · 20.9 miHorses · 1.0 miUnpaved · 27.8 mi
White Trail1.2 mi
Holliston Highway0.9 mi
Burial By-pass0.9 mi
Middle Sister0.6 mi
Blue Trail0.6 mi
The Main Trail0.6 mi
Right Turn Clyde0.6 mi
New Trail0.5 mi
Milford Byway0.5 mi
Dennis' Playground0.4 mi
15 more trails
Krusher
0.4 miSwamp Bypass
0.4 miYellow Trail
0.4 miKnee Jerk
0.4 miThe Intro
0.4 miThree Sisters
0.4 miSassafras Trail
0.4 miCollege Rock Run
0.3 miSwamp Side
0.3 miTeetering Rock Trail
0.3 miCemetery Run
0.3 miThe Gulley
0.3 miSudden Impact
0.3 miTonto
0.3 miYellow
0.3 miLakes & rivers tap for directions
Biking & sports
6.9 miles of bike routes
Bike lanes are often missing from the map in smaller towns, so that number is likely low.
6.7 mi
off-road bike paths
0.3 mi
shoulders & shared lanes
White TrailBike route
2.4 miCourts & fields
10Baseball
6Soccer
4Basketball
3Tennis
1Equestrian
1Lacrosse
1Football
1Pickleball
Includes school and college facilities, which aren’t always open to the public.
History along the way
History →5 places on the National Register
The country’s official list of places worth saving (National Park Service).
When to get out
The best walking months in Holliston: 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) | 9.4 | 10.5 | 11.8 | 13.3 | 14.6 | 15.2 | 15.0 | 13.9 | 12.4 | 11.0 | 9.7 | 9.1 |
| High (°F) | 36 | 39 | 47 | 59 | 70 | 78 | 84 | 82 | 75 | 63 | 51 | 41 |
| Rain (in) | 3.8 | 3.4 | 4.4 | 4.3 | 3.7 | 4.2 | 3.7 | 3.9 | 4.0 | 4.9 | 4.0 | 4.7 |
February is the driest month (3.4 in) and July the warmest (highs of 84 °F). 4.9 inches fall in October, the wettest month. The climate in Holliston →
Next door
Holliston and its neighbors
Tap a town to see its outdoors.
Questions about parks and trails in Holliston
Where can I hike in Holliston?
The longest trail networks: Town Forest, 6.7 miles; Fairbanks Land, 5.2 miles; Wenakeening Woods, 3.2 miles; Adams Street Conservation Land, 1.4 miles. Each one is on the map above, with directions to the nearest trailhead or parking.
How much of Holliston is conserved land?
24% of its land, against a typical 21% for a Massachusetts town and 4% nationally (PAD-US). Conserved doesn’t always mean open to visitors: easements are usually private land.
Are dogs allowed on Holliston’s trails?
Town Forest and Fairbanks Land don’t have dog rules recorded on the map; check the signs at the trailhead.
Where can I bike in Holliston?
6.9 miles of bike routes are on the map: 6.7 of off-road paths and 0.3 of shoulders and shared lanes. Named routes: White Trail.
Is there public land near Holliston?
48,393 acres of parks and open public land lie inside Holliston or within 10 miles of it (PAD-US), 1,949 of them inside the town line.
How much outdoors does Holliston have?
Among the top 1% of U.S. towns on the Outdoors grade, #58 of 283 in Massachusetts. 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 Holliston 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 →