Transit friendly
Dogs Allowed



At Middlesex Fells, you can hike, bike, fish, or let your dog run free in the off-leash area. Rent a canoe or kayak to explore Spot Pond.


Sunrise to sunset


  • Sheepfold parking area, Rte.28 (open 9:00 a.m. to dusk)
  • Flynn Rink, the Botume House and Virginia Wood on Woodland Road
  • Greenwood Park, the Stone Zoo and one "pull-off" on Pond Street
  • Straw Point Parking Area on corner of South Street and Rte.28
  • Bellevue Pond, Long Pond and other "pull-offs" along South Border Road
  • Jerry Jingle Park on Lynn Fells Parkway (please use caution crossing to reservation)
  • Crystal Springs Parking Area on Lynn Fells Parkway
  • Additional "pull-off" on Fellsway East


A person walking through trails.

Hiking & walking

With over 100 miles of mixed-use trails, there is plenty to see and explore for all difficulty levels.
Kayaking across Spot Pond.


Rent a kayak or canoe and explore Spot Pond, right in the heart of Middlesex Fells.

Mountain biking 

Take in the scenery on the Mountain Bike Loop around the Western Fells. If you’re looking for a challenging trail, check out the Reservoir Trail.

Off-leash area 

Let your four-legged friend play freely in Sheepfold Meadow.

All Activities

  • Biking
  • Boating (non-motorized)
  • Canoeing and kayaking
  • Cross-country skiing
  • Educational programs
  • Fishing
  • Hiking
  • Horseback riding
  • Mountain biking
  • Sailing


  • Athletic fields
  • Dog park
  • Grills
  • Observation tower
  • Picnic area
  • Playground
  • Visitors center
  • Weddings


  • Biking
  • Canoeing & kayaking
  • Cross-country skiing
  • Educational programs
  • Fishing
  • Hiking & walking
  • Horseback riding
  • Mountain biking
  • Non-motorized boating
  • Sailing


  • Accessible boating
  • Accessible fishing
  • Accessible hiking trails


  • No trespassing on Town of Winchester Water Supply Lands
  • No fires
  • No camping
  • No swimming
  • No motorized vehicles
  • No more than 3 dogs allowed per person
  • Avoid unpaved trails when wet
  • Do not go off-trail
  • Dogs must be on a leash (Unless in designated off-leash area)
  • Mountain biking only allowed on designated trails
  • No personal vessels allowed on the water


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