Guided Walks & Events

Guided Walks For Fall 2021

 Come along to enjoy some of Wellesley’s beautiful open spaces and discover trails that will expand your recreational options!  The walks are free, and no registration is required. Most walks cover 1.5 to 2 miles and last about one hour. Participants are encouraged to wear sturdy footwear.  Walks take place unless it pours rain or there are high winds.  

Participants will be required to follow Town guidelines for COVID-19 for outdoors group events.  If the walk is cancelled because of the pandemic, a notice will be posted on our website at

Guernsey Sanctuary Trail

September 26, Sunday (10:30-11:30 a.m.)

Explore Guernsey Sanctuary, a 25 acre reservation owned by the Wellesley Conservation Land Trust.  The sanctuary was part of the William Emerson Baker estate and the site of his 1870’s amusement park on Sabrina Lake.  Meet at the Guernsey parking area.  Take Dover Road from Washington Street and follow for 0.7 mile. Turn right onto Livingston Road, which becomes Winding River Road, and follow for 0.9 mile.  Small parking area is on your left at the trail map house. For other cars, please park on the right along Winding River Road. 

North Forty Trail 

October 2, Saturday (9:00-10:00 a.m.) 

Walk this new trail in the North Forty and view the vernal pool from at the recently built boardwalk. This easy and enjoyable walk will take trails adjacent to the Crosstown Trail along the Cochituate Aqueduct.  Go through woodlands and a pine forest and see the community gardens. Meet at the gate to the town beach, located at the end of Turner Road, 0.3 mile west of Weston Road. Please park on the wooded side of Turner Road. 

Town Forest Trails 

October 16, Saturday (9:30-10:30 a.m.) 

Join us for a pleasant walk on the woodland trails in our Town Forest.  The forest is the largest reservation in Town and supports a wide variety of wildlife and birds in a natural environment.  Walk along the Longfellow Pond shoreline and see the remains of a once vital ice house.  Climb to the top of a high spectacular esker deposited by glaciers.  Meet at the Longfellow Pond parking lot, located on the left side of Oakland Street 0.9 mi. south of Rt. 9.   

Boulder Brook Trail 

October 31, Sunday (10:30-11:30 a.m.)

Explore this open-space jewel and walk the woodland and meadow trails adjacent to the Bates School in Kelly Memorial Park and Boulder Brook Reservation.  See large glacial erratics and landscape carved by the glaciers. Climb to the top of Rocky Ledges.  Meet at the Kelly Memorial Park parking lot, located on the left side of Elmwood Road 0.3 mi. east of Weston Road.

We look forward to seeing you!  Walks take place unless it pours rain or there are high winds.