Best Trails near Winchester, Massachusetts

Quiet and scenic. Lots of wildlife and add on trails to make the walk longer if desired. I walk this almost everyday.

One of the best hiking trail in the Boston area. The views is absolutely incredible and the sunset is wonderful too. This trail is relatively short so I usually combine it with other trail.

I also seldom complete this trail without a detour up Bear Hill as well. I enjoy the climb and the view from Bear Hill tower. And other times, I combine it with the trail that goes through the Middle and South Reservoir as well.

Nice walk with the family.

a nice trail around the pond. great little hike up horn pond mountain!

really nice area to run. the are lots of secondary trails cut in and out so you can lose your way if you start exploring them.

Fairly easy trail, conveniently located. Long Pond is nice, but there aren’t many other interesting features.

Running trail... excellent place to relax and right on the road so easy access

A decent walk around Horn Pond. This trail only goes around the pond, providing some nice water views. There are other nearby trails which provide access to Horn Pond Mountain, which has interesting scenery and views of the Boston skyline.

Parking lot at (42.4496220,-71.1257951). Nice, short walk.

Principally a pine forest on shallow soil over glacial stoney rubble. Mostly ~50 year old tree. Just few older. The trail rounds the small shallow lake mostly above. Petty views of that water. At the highest point a short detour to the west reveals an excellent vista. Pine forests, in my opinion, are a bit dull. The Fells are popular, this trail is less crowded than others.

Took a different path than what's mapped here. As another reviewer suggested, I parked on Woburn Parkway and walked along the gravel/sometimes paved path around the pond, but then veered away from the water up a slight hill and then down again. The footing there is rockier and woodsier, but not really hiking. Still, be careful with the loose rocks going downhill :) Nice location away from car-traffic, with a taste of nature in an otherwise densely populated neighborhood. Distance: 3.8m

My best place. Highly recommend

Great Place to run around the Horn Pond.

Nice area - you can go off on to dirt trails more in the woods or stay on the paved paths. Good for a quick run but not a real hike.
My only complaint is with the directions provided when you click on directions from All Trails - it leads you to a residential neighborhood quite a distance from the pond. I figured out to go to Woburn Parkway which ends at the pond. There is some on street parking there.

enter horn pond from Sturgis Street parking. GPS to corner of Beacon and Sturgis. main strip is paved, great for kids on bikes. trails in the woods were easy, but beautiful and relaxing.

5 stars because I live a 10 minute walk from Horn Pond. very clean park. great walk to balance a leisurely walk on paved paths or hit the trails in the woods.

Walk there all the time. Pleasant.

I live nearby and "walk the pond" frequently.The pond is 2.5 miles around with a few loops into the trees if you want a little elevation. There is plenty of parking in the lot on Lake street and along Arlington Road. I do not know why this map shows a tail starting near the Joyce School on Cambridge road because that is not even close to the pond. Very nice walk and paved all around the pond.

Great hike, lot of changes in elevation, or just walk the Ponds

Love it here, beautiful views

Good trail near my house so I use it all the time. Familiarity may be influencing my score.

The scenery was very pleasant, the water in the pond was very calm and blue. We seen people walking along the path, some with kids and dogs. We were quite delighted by how nice a retreat it was in the middle of a busy city. There are a few hills one could climb, apparently where the moderate rating came from.

A big swampy circle but it's fun

my home city.. horn pond mountain has a amazing Indian bowl on it good for a little adventure

Beautiful, quiet great for running and biking

I chose to enter Horn Pond's Trail from the hospital located off of 3A. There is a path not far from the parking lot, which brings you to the summit of the Woburn Reservoir hill. It was a difficult climb for someone as out of shape as me but, the sweat was worth the view. You can see all of Horn Pond and it's stunning. One of my favorite spots if you're looking for privacy, a view, and some exercise.

Relaxing walk around the pond.