Southern Woodlands Reservation
Managed by Martha's Vineyard Land Bank Commission
238 acres3.7 mi of trail
Road to Farm Neck
Dog rules not recorded
Directionsto the parking lotWebsite ↗
Photo: Elkman at en.wikipedia · CC BY-SA 3.0A+Outdoors
Outdoors in Oak Bluffs
Oak Bluffs has 22 miles of mapped trails, 3.0 for every square mile of land
19% of Oak Bluffs’ land is conserved, about 880 acres. 336 acres are parks and preserves, 62 per 1,000 residents. The biggest trail networks: Southern Woodlands Reservation (3.7 mi), Trade Winds Field Preserve (1.3 mi), Wapatequa Wood (0.6 mi).
Ahead of 96% of U.S. towns · #141 of 283 in Massachusetts. What drives it
Conserved land
19%
880 acres · of 7.3 sq mi of land
Trails
22 mi
3.0 per sq mi of land
Park land
336 ac
62 acres per 1,000 residents
Near a park
87%
of residents within ½ mile
Bike routes
10 mi
10 mi paths
Highest peak
26 ft
Telegraph Hill
Lakes & rivers
7
24 beaches
What kind of outdoors town is Oak Bluffs?
Read from the map. The page puts what stands out first.
Outdoors grade
How much outdoors does Oak Bluffs have?
On conserved land, trails, park land and how close residents live to a park, Oak Bluffs is ahead of 96% of U.S. towns, #141 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 Oak Bluffs’ overall grade.
Conserved land19% of the land · typical MA town 21% · U.S. 4%ATrails3.0 miles of mapped trail per square mile of land (22 mi) · MA 1.9 · U.S. 0.4A+Park land62 acres of park per 1,000 residents (336 acres) · MA 91 · U.S. 13A−Parks close to home87% of residents within a half mile of a park · MA 93% · U.S. 72%B+
All U.S. towns we grade (21,298)Ahead of 96%
LessMore
Massachusetts towns of 2,500+ (283)Ahead of 50%
Massachusetts towns conserve more land than most (a typical one, 21%; the U.S., 4%), so Oak Bluffs’ 19% is ahead of 39% of Massachusetts towns, while its trails per square mile lead 75% of them.
Water is more than half of Oak Bluffs’ area (19 of 26 square miles), so every share here is of land; over land and water together, the conserved share would read 5%.
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 Southern Woodlands Reservation, with 3.7 miles. Directions go to the nearest trailhead or public parking.
Trade Winds Field Preserve
Nature preserve
72 acres1.3 mi of trail
Dog rules not recorded
Directionsto Trade Winds Preserve Parking
Wapatequa Wood
Nature preserve
26 acres0.6 mi of trail
Dog rules not recorded
Directionsto the trail sign
Farm Pond Preserve
Nature preserve
20 acres0.5 mi of trail
Dog rules not recorded
Directionsto the parking lot
Featherstone Farm
Nature preserve
15 acres0.5 mi of trail
Dog rules not recorded
Directionsto the parking lotWebsite ↗
Lakeside Park
Park
12 acres0.3 mi of trail
Dog rules not recorded
No trailhead mapped yet
All 31 parks & preserves
Southern Woodlands Reservation238 acres · 3.7 mi of trail · Martha's Vineyard Land Bank Commission
DirectionsTrade Winds Field Preserve72 acres · 1.3 mi of trail
DirectionsWapatequa Wood26 acres · 0.6 mi of trail
DirectionsFarm Pond Preserve20 acres · 0.5 mi of trail
DirectionsFeatherstone Farm15 acres · 0.5 mi of trail
DirectionsOcean Park8 acres · 0.4 mi of trail
DirectionsLakeside Park12 acres · 0.3 mi of trail
Trinity Park3 acres · 0.3 mi of trail
DirectionsNiantic Park3 acres · 0.2 mi of trail
Waban Park8 acres · 0.1 mi of trail
Washington Park5 acres · 0.1 mi of trail
Prospect Park2 acres · 0.1 mi of trail
DirectionsWaterview Farm20 acres
Convery Land11 acres
East Chop Cliffs6 acres
DirectionsSumner Park5 acres
East Chop5 acres
Mill Square Park4 acres
Eastville Point Beach4 acres
DirectionsVeira Park3 acres
Morton Park2 acres
Eastville Beach Jetty2 acres
Nashawena Park2 acres
Arlington Park2 acres
Oriental Park2 acres
Hiawatha Park1 acres
Naushon Park1 acres
Forest Park1 acres
Plymouth Park1 acres
Hartford Park1 acres
Leslie Park1 acres
Who protects it
880 conserved acres
19% of Oak Bluffs’ land. Water is left out: Oak Bluffs has 7.3 square miles of land and 18.6 of water, so the share counts land only. Who manages Oak Bluffs’s conserved land, from the USGS Protected Areas Database. Approximate, because parcels can overlap.
Other or Unknown Local Government254 ac
Town or city107 ac
Land trusts & nonprofits6 ac
County2 ac
Not recorded535 ac
Local Conservation Area · 236 acPrivate Other or Unknown · 208 acPrivate Conservation · 123 acWatershed Protection Area · 95 acConservation Easement · 60 ac
Good to know
Conserved doesn’t always mean open to visitors. 30 acres are conservation easements, usually private land. Public access isn’t recorded for 8 of 75 parcels. The walks above are places people visit.
The biggest protected parcels
| Parcel (PAD-US) | Managed by | Acres | Public access |
|---|---|---|---|
| Farm Neck Golf Club Private Other or Unknown | Not recorded | 208 | Restricted |
| Southern Woodlands Reservation Local Conservation Area | Other or Unknown Local Government | 188 | Restricted |
| Wapatequa Woods Preserve Private Conservation | Not recorded | 75 | Open |
| Joseph Sylvia State Beach State Park | Not recorded | 59 | Open |
| Water Department Land Watershed Protection Area | Not recorded | 59 | Unknown |
| Weahtaqua Springs Preserve Local Conservation Area | Other or Unknown Local Government | 28 | Restricted |
| Oak Bluffs Water Department Watershed Protection Area | Not recorded | 20 | Unknown |
| Sail Camp Local Other or Unknown | Not recorded | 20 | Open |
| Featherstone Farm Local Other or Unknown | Other or Unknown Local Government | 18 | Unknown |
| Pecoy Point Preserve Local Conservation Area | Other or Unknown Local Government | 17 | Restricted |
5 smaller protected places aren’t shown.
Things to do
27 places to go in Oak Bluffs
Beaches, playgrounds, peaks, falls and more. Pick a kind.
Beaches in Oak Bluffs
Doug's Cove
DirectionsEastville Beach
DirectionsMartinelli Beach
DirectionsSeaview Beach
DirectionsThe Inkwell Beach
DirectionsTown Beach
DirectionsPlus 18 beaches without a name on the map. Tap “Show all on map” to see them.
Playgrounds in Oak Bluffs
2 playgrounds without a name on the map.
Peaks in Oak Bluffs
Telegraph Hill26 ft elevation
DirectionsTrails & water
9 named trails and 7 lakes & rivers
Named trails
Open to bikes · 0.5 miUnpaved · 4.1 mi
Road to Farm Neck0.8 mi
Fire Road A0.7 mi
Road to Wapatequa0.5 mi
Elderberry0.1 mi
Holly0.1 mi
Lilac0.1 mi
Farm Pond Trail0.1 mi
Dogwood0.1 mi
Magnolia0.1 mi
Lakes & rivers tap for directions
Biking & sports
10 miles of bike routes
Bike lanes are often missing from the map in smaller towns, so that number is likely low.
10 mi
off-road bike paths
Courts & fields
26Tennis
7Baseball
7Pickleball
4Basketball
2Football
1Skate park
Includes school and college facilities, which aren’t always open to the public.
History along the way
History →7 places on the National Register, 2 of them National Historic Landmarks
The country’s official list of places worth saving (National Park Service). The map also marks 4 historic points from OpenStreetMap: plaques, memorials and old buildings.
When to get out
The best walking months in Oak Bluffs: May 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) | 40 | 41 | 46 | 55 | 64 | 73 | 80 | 79 | 73 | 63 | 53 | 45 |
| Rain (in) | 3.9 | 3.5 | 4.8 | 4.2 | 3.5 | 3.4 | 2.7 | 3.4 | 4.1 | 4.7 | 4.2 | 4.8 |
July is the driest month (2.7 in) and the warmest (highs of 80 °F). 4.8 inches fall in March, the wettest month. The climate in Oak Bluffs →
Next door
Oak Bluffs and its neighbors
Oak Bluffs has the second most mapped trails of the 3 towns around it. Tap a town to see its outdoors.
Questions about parks and trails in Oak Bluffs
Where can I hike in Oak Bluffs?
The longest trail networks: Southern Woodlands Reservation, 3.7 miles; Trade Winds Field Preserve, 1.3 miles; Wapatequa Wood, 0.6 miles; Farm Pond Preserve, 0.5 miles. Each one is on the map above, with directions to the nearest trailhead or parking.
How much of Oak Bluffs is conserved land?
19% 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 Oak Bluffs’ trails?
Southern Woodlands Reservation and Trade Winds Field Preserve don’t have dog rules recorded on the map; check the signs at the trailhead.
Where can I bike in Oak Bluffs?
10 miles of bike routes are on the map: 10 of off-road paths.
Is there public land near Oak Bluffs?
19,147 acres of parks and open public land lie inside Oak Bluffs or within 10 miles of it (PAD-US), 337 of them inside the town line.
How much outdoors does Oak Bluffs have?
Ahead of 96% of U.S. towns on the Outdoors grade, #141 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 Oak Bluffs 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 →