Frequently Asked Questions

The easiest trail is the Brook Path, which follows the Caroline and Fuller Brooks.  It is an ADA-compliant, stone-dust path which parallels Washington Street and is easily accessible from the multiple cross streets.  The Longfellow Pond Trail is another easy trail, which circles this scenic pond in our Town Forest.  Other easy trails are listed online under Suggested Walks.

The Brook Path and the Longfellow Pond Trail are easy trails and great for kids.  We also recommend the Centennial Reservation Trail for a hike up to the top of Maugus Hill for a view of the Blue Hill, the Morses Pond Trail to the town beach and then continuing along the Crosstown Trail to view the pond, and the Boulder Brook Trail for a hike to the top of Rocky Ledges.

Most of the interconnecting trails are suitable for jogging.  The Brook Path and trails along the aqueducts provide level surfaces with good footing, and the Guernsey Path and Beard Trail also provide good jogging routes.  If you enjoy long jogs, take the Wellesley Grand Tour, a 10.8 mile loop using all five of our interconnecting trails.

Maps and guides are available online, at map dispensers located at trail parking lots and trailheads, in the west lobby of Town Hall and at the Town Clerk’s Office.  You can get trail maps for all the town trails and detailed trail maps for Boulder Brook Reservation, Centennial Reservation, Morses Pond and the Town Forest.

With an early awareness of the importance of protecting our natural resources and careful town planning, Wellesley has 2,700 acres of open space. We are also fortunate to have two aqueducts running through town that serve as interconnecting greenways, along with a historic linear park. As a result we have 46 miles of trails in Town, and 28 miles are marked with trail markers.

There are fourteen trails in Wellesley, and most likely there is a trail near your home, school or business.  We have ten woodland trails that go through conservation lands, parks and open space, and five interconnecting trails that run along aqueducts, parks and roads.

The shortest trail, the Rockridge Pond Trail, is 0.4 miles long and is a pleasant walk around the edge of this scenic pond.  Our longest trail, the Crosstown Trail, is 6.2 miles long and runs along the Cochituate Aqueduct from the east to the west side of town.

Come on one of our free guided walks.  We run walks in the spring and fall.  The walks are at an easy pace, less than two miles long, and last about one hour.  Look for walk schedules on our website, announcements in the Townsman's Community Bulletin Board, and fliers posted on our map houses.

Yes, dogs are welcomed on our trails.  The dog can be off-leash if under voice control by the owner.  We encourage walkers to pick up after their dogs and properly dispose of the waste.  Remember that the town has a restriction on the number of dogs on conservation land:  No more than two dogs per person, or three dogs with a permit.

Yes, our trails are used by bicyclists for recreation and commuting, and by children going to school.  The most popular bicycling trail, and frequently used by families, is the Brook Path because of its level surface.  Note that all motorized use of the trails on open space lands is prohibited.

The Brook Path, the lower meadows at Centennial Reservation, and trails along the aqueducts are ideal for cross-country skiing.  The section of the Crosstown Trail from Weston Road to Rt. 9 is a favorite, with scenic views of Morses Pond and only two road crossing. The Guernsey Path from the trailhead at Winding River Road to the Nehoiden Golf Course is another picturesque trail with only one road crossing.

Please report trail problems to the Natural Resources Commission Office.  Call us at 781-431-1019, extension 2294, or email us at trails@wellesleyma.gov.

Please come to one of our monthly trails meetings, meet our committee members, and learn about our projects and plans. We are a volunteer town committee, and welcome people who would like to join the Trails Committee to help us monitor and maintain the trails.  Not interested in becoming a committee member?  Then consider joining the Friends of Wellesley Trails to help us with events and projects and contact us at trails@wellesleyma.gov.