Spring 2026 - Guided Trail Walks

Join your Wellesley neighbors and members of the Wellesley Trails Committee on guided trail walks.  No registration required and all walks are free. Walks take place unless it pours rain and there are high winds.  Participants are encouraged to wear sturdy footwear. 

2026 Spring Trails Flyer

Sudbury Path and Waban Arches - 2.4 miles

Friday, May 8 - (10 a.m. - 11:15 a.m.)

Enjoy this diverse walk with an aqueduct, a brook that feeds the Charles River, the Charles River itself, a sanctuary, and a historical building.  See beautiful views into Needham and Natick from the top of the Waban Arches.  Walk along the Charles River at multiple points in the walk and learn of the many side trails you can take in future walks by yourself or with friends.  Meet at the parking area at the trail head.  GPS: 165 Winding River Road, Wellesley

Hemlock Gorge - 1.0 miles

Friday, May 16v- (10 a.m. - 11:15 a.m.)

Chances are you never visited Hemlock Gorge and walked its near silent trails.  And chances are you never trod the deck of the seven-arched Echo Bridge and looked down upon what was once a field dotted with wigwams. Come explore the trails and bridge in Hemlock Gorge, a scenic and historic area along the Charles River at the corners of Wellesley, Needham and Newton.  While there, you might hear the echo of your own voice and imagine the sounds of a bygone time.  Meet at the Echo Bridge Office Park parking lot, at 381 Elliot Street, Newton.  Park on the side of the lot facing the river.

Mini-Grand Tour - 6.5 miles

Saturday,  June 6 -  (10 a.m. - 12:30 p.m.) 

Join us for a 6.5-mile, 2.5+ hour Mini-Grand Tour that links a selection of our favorite trails, with a few sidewalks in between.  From Longfellow Pond, we will find our way to Centennial Reservation, the Crosstown Trail at Indian Springs Park, John G. Schuler Path, Hunnewell Fyffe footbridge, Charles River Path, Oullet Park, and Barton Road trail, before returning to the Town Forest.  While not as long as the Grand Tour, the Mini Tour is more strenuous than our typical walk.  Remember to bring water and wear sturdy walking shoes.  Meet at the Longfellow Pond parking lot at 220 Oakland Street.

Centennial Reservation- 1.8 miles 

Saturday, June 13 - (10 a.m. -11:15 a.m.) - 1.8 miles

Take a picturesque walk, through rolling meadows to the top of Maugus Hill, one of the highest points in Wellesley.  View the beautiful Great Blue Hills in Canton from a hillside meadow overlooking the town of Needham.  Then, descend through the meadow and around Benzanson Pond, a favorite swimming hole for dogs as well as frogs and tadpoles.  Come explore this conservation land purchased by the town for Wellesley's 1981 Centennial Celebration and now one of the most popular trails in Wellesley. This walk also includes Mass Bay land that is maintained by the Wellesley Trails Committee and the Wellesley DPW.  Meet at the Mass Bay parking lot off of Oakland Street, (not the Centennial lot).

We look forward to seeing you!  

If you have any  questions about these guided walks please email: trails@wellesleyma.gov