Guided Walks & Events

Come along to enjoy some of Wellesley’s beautiful open spaces and discover trails that will expand your recreational options. The walks and events are free, and no registration is required. Most walks cover 1.5 to 2 miles and last about 1 hour. Participants are encouraged to wear sturdy footwear.

Activities take place unless it pours rain or there are high winds.  

We look forward to seeing you!

This is a tentative schedule because of the COVID-19 pandemic. Please check back for cancellations and if dogs on leash will be permitted on the walks. Also, Kids’ Trails Day has been cancelled for this year.

Walks and Events for 2020

Date Time Location
September 26 Saturday, 9:00-10:00 AM Morses Pond Trail
October 4 Sunday, 1:00-2:00 PM Boulder Brook Reservation
October 24 Saturday, 8:00-12:30 PM Wellesley Grand Tour Hike 
November 1 Sunday, 10:00-11:15 AM Brook Path & Crosstown Trail 


September 26, Saturday (9-10 a.m.) – Morses Pond Trail 

Walk the trails along Morses Pond, a 102 acre pond and a source for our town water wells. View the pond, islands and wildlife. The walk will take you through a pine forest along the Cochituate Aqueduct and along the shore line at the town beach.  Walk will include a fun outdoor exploration for kids.  Meet at the gate to the town beach access road, located at the end of Turner Rd., 0.3 mile west of Weston Road.  Please park on the wooded side of Turner Road.

October 4, Sunday (1-2 p.m.) – Boulder Brook Reservation

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, landscape carved by the glaciers and a scenic view from the top of Rocky Ledges.  Meet at the Kelly Memorial Park parking lot, located on the left side of Elmwood Road 0.3 mile east of Weston Road.

October 24, Saturday (8 a.m.-12:30 p.m.) – Wellesley Grand Tour Hike

Take a spectacular 11-mile loop hike along the trails network in Wellesley.  We will start along the Brook Path, then take the Crosstown Trail, Charles River Path, Sudbury Path and Guernsey Path, and return on the Brook Path.  Most of our hike will be on trails through woods or along aqueducts, with less than 3 miles along roads. Meet at the State Street parking lot adjacent to the High School stadium.

Note:  This is a strenuous hike and participants should plan to walk at a moderate pace to stay with the group. Bring sturdy footwear, water and a snack. One restroom stop included. No dogs please.

November 1, Sunday (10-11:15 a.m.) – Brook Path & Crosstown Trail

Explore trails that parallel Washington Street from Wellesley High School to Clock Tower Park.  We will start the walk on the Brook Path along the Caroline Brook to Maugus Ave, and then return to the High School along the Crosstown Trail. Meet at the State Street parking lot adjacent to the High School stadium.