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Southern Woodlands Reservation


234.0 acres


Motorists on the Barnes Road cannot fail to notice the sloping bluffs which rise from the tar, just opposite the Head of the Lagoon Pond. This escarpment marks the westerly edge of Oak Bluffs' southern woodlands, which stretch as far east as the County Road; a portion was formerly known to islanders as Webbs Camping Area. Trails here are especially well-suited to cross-country skiing.

Universal Access

  • Difficulty rating: Moderate
  • Trail: Park in trailhead off County Road or at Featherstone Farm. Trail from County Road trailhead is solid and wide. Trail from Featherstone Farm to views of field is mostly grass.
  • Points of Interest: Views from high side of sloping field and walking in shady woodlands
  • Benches: 0


Park in the trailhead at the Featherstone Farm (property no. 30) and follow map on signboard.

Historical Highlights

  • Harold Webb bought a portion of the western end of the reservation in 1936; he was a police officer in Tisbury in the 1940s and owned and operated a farm-to-home poultry and egg delivery business for 15 years
  • after the poultry business ended due to the rise in poultry farming costs he developed Webb’s Campground; he and his wife owned and operated the campground for 25 years