Wellesley Hike – Kelly Memorial Park and Boulder Brook Reservation


The first thing I noticed was the welcoming committee of robins, more than a dozen of them flitting around Kelly Memorial Park on a 40-degree February morning. According to Mass Audubon, common songbirds overwinter here or have descended earlier in the season from more northerly points in New England or Canada. They thank you for your garden feeders. The next hello came from a friendly, photogenic pup, emerging from the woods path. Behind him, a walker on crutches, despite the freezing conditions. Encouraged, I strapped on my Yaktrax and began my 1.6-mile loop walk from Kelly Memorial Park, through the Boulder Brook Preserve, to the top of the rock ledges, then back down via a short jump to the border to Weston, and back to the Elmwood Road parking lot.

The dirt parking lot at Kelly Memorial Park on Elmwood Road can accommodate approximately 10 cars. The sign above is at the trailhead.

For this hike I followed the purple arrows. There are many side trails in the Kelly Field and Boulder Brook areas, which makes the area so popular with kids and families who want to get out and run in nature. But for today, I stayed on the most traveled path.

Kelly Memorial Park, Forest Road, Wellesley
The Purple Arrow Trail leads to Kelly Fields and Katharine Lee Bates Elementary School.
Fairy Rock, Wellesley
As I was walking up the path from the Kelly parking lot, I quickly came across Fairy Rock, a popular climbing spot for kids. On the right side of the path is a winding stone wall, a remnant of the area’s agricultural days.
Katharine Lee Bates School, Wellesley
Katharine Lee Bates School, Wellesley

The path opens to a view of Kelly Field and Katharine Lee Bates Elementary School beyond the playgrounds. In warm weather, the field is full of teams taking advantage of the four baseball diamonds and multiple football zones. I kept to the left and walked along the paved part of the path that continues behind the baseball net and along Boulder Brook.

Boulder Brook Reserve, Wellesley

Boulder Brook Reserve, Wellesley
The wooden bridge leads to the Boulder Brook Reservation Meadow, a 31-acre parcel that was once part of Boulder Brook Farm, a working dairy farm in the 1900s. The property was purchased by the City in 1966.
Boulder Brook Reserve, Wellesley
A mowed path through the prairie is maintained by the city in the spring, summer, and most of the fall. At the end of autumn, the entire meadow is mowed to avoid reforestation of the area. Follow this path which curves to the right and into the woods.
Elephant Rock, Wellesley
Elephant Rock, Wellesley

As I entered the woods, I kept an eye out for Elephant Rock on the left, another great climbing rock for the kids. From there I headed to Rocky Ledges, a popular place to see the sunset in Wellesley.

Boulder Brook Preserve, Bridge
This bridge was built about ten years ago as part of an Eagle Scout project by Peter Shellito, Troop 185.

Boulder Brook Reservation

Once over the bridge, I took the trail to the right and found the base of the rock ledges. This was probably the hardest part of the hike to find the trail. It was also maybe a little misguided of me to continue given the freezing conditions, but I’m stubborn that way.

Boulder Brook Reservation
I felt lucky to have reached the top of the rock ledges. Wellesley College is on the left and Pegan Hill in Natick is on the right, but even with the leaves on the trees I couldn’t see them. The trees have really grown in the last ten years.
Boulder Brook Preserve, Weston Area
Weston part of the hike.

On the way down I walked past Weston as you can tell by the trail marker which has a green pine on a white background. It was a steep section, made more difficult by the ice. Very few people have been down here lately.

Boulder Brook Preserve, Bridge

Once I got to the bottom of the ledges, I took the purple trail one more time, kept to the right and retraced my steps over the Eagle Scout Bridge.

Boulder Brook Reservation, Bench, Wellesley

I stayed to the left of the bench and went back to the meadow.

Boulder Brook Reserve, Wellesley

As I retraced my steps on the prairie, the robins again showed up and kept me company until I crossed the Boulder Brook bridge back into the Kelly Field area. The hike took about an hour. I will be back in the spring when the robins are joined by many other species of birds and other wildlife.


Wellesley Trails Committee shares 6 guided hikes on the trails

Beyond Wellesley: A 3km hike around Weston Reservoir

You can see Mount Monadnock on a beautiful winter day from Pegan Hill

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