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Backcountry Skiing at Rocky Woods

What to Bring

Hat   Gloves
Sunglasses   Sunscreen
Daypack with
lunch
  Ski equipment (see below for rentals)
Hot chocolate or
tea in vacuum
bottle
  Water (hydration bladder
recommended)
Warm clothing
(layers that can be added and
removed)
   
 

Specs

  Directions
 
From Boston:
Take the Mass Pike (I-90) to I-95 South/Rte 128 South
Take exit 16B and follow Route 109 west for 5.7 mi. through Westwood and into
Medfield
Take right hairpin turn onto Hartford Street in Medfield
Follow for 0.6 mi. to the entrance to Rocky Woods Reservation on the left
  Good to know in advance
 
Open year-round, daily, sunrise to sunset

Sign at entrance indicates time gates are
locked

Admission fee: adult $3, child (12 and
under) free. Fees collected by ranger on
weekends and holidays; honor system at all other times

Free trail maps available at the parking area or available online for download or through mail order ($2 mail order fee, including
shipping)

Restrooms at the visitor center
  Etiquette
 
Stay on trails
Bring back your trash
Dog walking allowed for Trustees of
Reservations members with Green Dogs
permit only. Membership and Green Dogs
permits available from ranger on the
weekends, or by calling 508/785-0339
during the week
 
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Backcountry Skiing at Rocky Woods
 
 

ID Card

Overall rating: Four-Star Rating Four-Star Rating Four-Star Rating Four-Star Rating
Difficulty: 2/5
  Time from Boston: 30 minutes
  Duration: A few hours
  Cost:

$3 per person

  Main activity:

XC Skiing

 
 
 
 
This 500-acre reservation just 30 minutes from Boston offers more than six miles of backcountry skiing through a rolling landscape of granite ledges and giant boulders. Rocky Woods is the perfect destination to take advantage of a fresh snowfall, with scenic vistas, interesting terrain and nearly no visitors in the wintertime.

Rocky Woods is best known as a warm-weather destination, offering great hiking and catch-and-release fishing in Chickering Pond. But when deep snows fall in the region, cross-country skiing is the activity of choice. The miles of former woods roads and footpaths through rolling hills of white pine and red oak offer a spectacular backdrop for a superb un-groomed backcountry experience.

Although Rocky Woods is well-kept secret, it's a popular enough area that you won't likely have to break trail unless you arrive early in the morning after a mid-week snow storm.

The directions below will allow you to do either a short loop with great vistas, or a longer trip around the reservation; in both cases, the map will come in quite handy, though trail markers make orientation relatively easy.
Your workout in Rocky Woods begins on the Loop Trail, with a trail head next to the ranger station at the entrance and at the far end of the parking lot
Take Loop Trail to Echo Pond Trail, at the trail intersection marked "1"
Follow Echo Pond Trail to the East and West Trail, past intersection 17, leaving the pond on your right, and past marker 16.
At this point, decide between a shorter ski with the opportunity for fantastic views, or a longer ski through more of the property.
For the shorter trip with great views:
Turn right at intersection 16 onto Hardwood Notch Trail; after a short while you'll pass Echo Pond on the right
At intersection 6, cross over Quarry Trail and continue climbing
Just as Notch Pond appears on your left, look for a short looping trail to your right: this unnamed spur takes a short climb to a scenic vista
Continue on this short trail back to Hardwood Notch Trail. You'll see a large glacial erratic (a boulder carried from far away by ice movement) known as Whale Rock
Shortly after this, the trail will intersect with Ridge Trail at marker 7. Turn right onto Ridge Trail, and again take the spur on the right to a scenic vista
This spur is a one-way track, so do an about-face after you've had a rest and enjoyed the view
After a few minutes back on Ridge Trail, you'll see a left trail climbing up toward a hemlock knoll. The steep climb is rewarded with a fun downhill that takes you back to Ridge Trail
Ridge Trail will take you down to Chickering Pond, and there are trails that ring the pond on either side
At the far end of the pond is the visitor center, and just beyond the visitor center is a trail leading back to the parking lot.
If you opt for a longer ski loop:
At intersection 16, keep going on East and West Trail (ahead)
Stay to the left at intersection 15. The East and West Trail ends at the intersection with Cheney Pond Trail (marker 14). Turn right onto Cheney Pond Trail to intersection 13
At marker 13, you have the option of continuing on level Cheney Pond Trail to the longer Wilson Swamp Trail, or taking the steeper Ridge Trail over Mine Hill. Either choice will take you to the northern portion of the reservation
Eventually you will hit trail marker 8, then 7
At marker 7, go north on Ridge Trail, and take the spur on the right to a scenic vista; this spur is a one-way track, so do an about-face after you've had a rest and enjoyed the view
After a few minutes back on Ridge Trail, you'll see a left trail climbing up toward a hemlock knoll. The steep climb is rewarded with a fun downhill that takes you back to Ridge Trail
Ridge Trail will take you down to Chickering Pond, and there are trails that ring the pond on either side
At the far end of the pond is the visitor center, and just beyond the visitor center is a trail leading back to the parking lot.
Depending on your pace and number of stops, you can expect skiing between 45 minutes and an hour and a half.
When spring comes in and biking becomes an option, you can further explore the area with the reservations ride.