Guided Walks & Events

Guided Walks For Spring - 2024

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. 

North Forty

Friday, April 26 - (10-11:00 a.m.) - (1.0 mi)

Discover the trails in the North Forty and view the vernal pool from the recently built boardwalk. This easy and enjoyable walk will take trails adjacent to the Crosstown Trail along the Cochituate Aqueduct. Go through the community gardens and woodlands, and see a 215 year old pine tree.  Meet at the North 40 trailhead located on Turner Road a short distance from Weston Road.  Please park on the wooded side of Turner Road.

Centennial Reservation

Saturday, May 4 - (9:00 - 10 a.m.) - (1.8 mi)

Explore conservation land purchased by the town for Wellesley's 1981 Centennial Celebration.  Take a picturesque walk in the woodlands and rolling meadows to the top of Maugus Hill, one of the highest points in Wellesley.  From the top of the upper meadow, view the Great Blue Hills in Canton.  Meet at the Centennial Reservation trailhead at the top of Maugus Ave. Directions: Take Maugus Avenue, which starts off Washington Street at Clock Tower Park, to the cul-de-sac trailhead, and park along the roadway. 

Waban Arches and Guernsey Sanctuary

Saturday, May 18 - (9:00 a.m.-10:00 a.m.) - (2.1 mi)

For Wellesley’s Wonderful Weekend, walk along the Charles River to the historic Waban Arches built in 1876 for the Sudbury Aqueduct and view the Charles River from the top of the 50-foot arches.  Also walk the Guernsey Sanctuary to Sabrina Lake, the 1870’s site of an amusement park.  Meet at the Guernsey parking area.  Directions:  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 opposite side of Winding River Road from the parking area.

Charles River Reservation Trail

Saturday, June 1 - (1:00 - 2:00 p.m.) - (0.9 mi)

New - Celebrate National Trails Day and take this scenic, easy, short walk along the Charles River at the Wellesley Office Park. The trail is ADA accessible and has multiple stops along the paved pathway with views of the river.  Meet at the Wellesley Office Park parking lot behind the 45 William Street offices. Directions: Take Route 9 east toward Newton, exit at the first ramp after the I-95 interchange (to Chestnut Street), and at end of ramp turn left onto Quinobequin Road in Newton. After passing under the Route 9 bridge, take an immediate left for the Route 9 westbound ramp. Before merging with Route 9, take the first right onto William Street. In 0.2 miles turn right at 45 William Street driveway, go under the building, head toward the river, and bear right for public parking signs at the trailhead.


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

2024 Guided Trail Walks