Maps, Guides & Descriptions

Sign At Wellesley Trail
Trail Post With Stickers

Trail Descriptions

Beard Trail (1.1 miles, purple arrows)

Follow a woodland trail through Ridge Hill Reservation along the Needham border. The start of this trail is at Beard Way off Grove Street at the Needham town line. The trail goes along an easement paralleling Beard Way and enters Ridge Hill Reservation in Needham. It continues to the gas pipeline, immediately turns left, and reenters the woods following a path to Cartwright Road. The trail then runs along Cartwright Road and ends at Beebe Meadow. 

Boulder Brook Reservation Trail (1.6 mile loop, purple arrows, elevation gain 140 feet)

Boulder Brook Reservation Map & Guide (PDF)

Walk through woodland trails and the meadow of the old Boulder Brook Farm to the top of Rocky Ledges. This trail starts at the parking lot on Elmwood Road at Kelly Memorial Park and goes through woods to the playing field adjacent to Bates School. It then crosses Boulder Brook, traverses an extensive meadow, and enters the woods below Rocky Ledges. Just after crossing the footbridge, the trail splits for a loop over the ledges. Take the trail to the right, follow to the base of the steep ledges and start your climb up the ledges. Follow the trail along the top of the ledges (be careful with children, steep drop-offs) and then descend steeply along the Weston town line. Follow the trail to the beginning of the loop and then back to the parking lot.

Brook Path (2.3 miles, pink arrows)

A pleasant walk on an ADA-compliant, stone-dust path along the Fuller and Caroline Brooks through Fuller Brook Park. This trail parallels Washington Street from Dover Road to Wellesley Hills but avoids the congestion and traffic of the downtown area.  The trail starts at Dover Road across from the Nehoiden Golf Course and follows Fuller Brook past the Hunnewell School to the State Street parking lot adjacent to the Wellesley High School stadium.  It then continues along the Caroline Brook to Maugus Avenue.  A short leg along Washington Street connects the trail to the Crosstown Trail at Cliff Road. 

Carisbrooke Reservation Trail (.5 mile loop, purple arrows)

Explore the rocky outcrops near the source of Cold Stream Brook. The start of this loop trail is at the end of Glen Brook Road, which is off Glen Road at the Weston town line. From the map house, the trail starts to the left, and goes past granite benches along Covati Pond. The trail crosses a footbridge over the Wellesley branch of the brook, loops around to the most western part of the reservation, crosses over the Weston branch of the brook and returns to the map house. 

Centennial Reservation (1.7 mile loop, purple arrows, elevation gain 200 feet)

Centennial Reservation Map & Guide (PDF)
Centennial Reservation Self-Guided Nature Trail (PDF)

Walk over rolling meadows and up Maugus Hill to view the Blue Hills. The trail starts at the Centennial Reservation parking lot off Oakland Street. This is a loop trail, and the start of the loop is at the first post in the meadow. Turn left and follow the trail down the meadow toward the golf course. The trail cuts through the woods to a meadow with bluebird houses, crosses a footbridge, goes up the meadow, enters the woods, and goes past the end of Maugus Avenue at the top of Maugus Hill, the trail descends toward Wareland Road and MassBay Community College and then ascends to the top of a meadow with a view south toward the Blue Hills. The trail then goes down the meadow to Bezanson Pond, where it completes the loop. 

Charles River Path (3.6 miles, red arrows)

Town Forest Map & Guide (PDF) - Southern section of trail

Explore the banks of the Charles River and climb eskers in the Town Forest. The trail starts off the Crosstown Trail at Indian Springs Park, goes along The Waterway and roads to the Charles River and follows the river along Boulevard Road in Lower Falls. It goes in back of the Waterstone complex to Washington Street and then follows Washington Street into Newton to the Mary Hunnewell Fyffe Footbridge at the Cordingly Dam. It crosses over the footbridge back into Wellesley, and snakes along the Charles River and I-95/Route-128 to Ouellet Park. It runs along Cedar Street, enters the Town Forest off Route-9 and proceeds over an esker to Longfellow Pond. It then crosses Oakland Street and climbs steep eskers along Rosemary Brook, ending at the Sudbury Aqueduct.

Crosstown Trail (6.0 miles, green arrows)

Morses Pond Map & Guide (PDF) - Western section of trail

A trail that takes you on a journey across Wellesley following the Cochituate Aqueduct. The Crosstown Trail starts at the town line where the Natick aqueduct trail enters Wellesley. It follows Overbrook Drive to Route 9, crosses at the traffic light, and continues east on Route 9 where it reconnects with the Cochituate Aqueduct bordering Morses Pond. The trail goes past Pickle and Pine Points and through the North 40 to the intersection at Linden Street and Weston Road. The trail then runs along Linden Street and Crest Road to Post Office Square, goes behind Town Hall to the Duck Pond and Morton Park, and then along Washington and State Streets to the Wellesley High School stadium parking lot. It continues along the Cochituate Aqueduct across Hunnewell Fields to Forest Street, then proceeds along Washington Street to Cliff Road, under Route 9 and follows roads to Woodlawn Avenue, where it rejoins the Cochituate Aqueduct. The trail continues along the aqueduct past Indian Springs Park and the Warren Building to Walnut Street. It then runs along Walnut Street to Cedar Street, rejoins the aqueduct, and ends at the intersection with the Charles River Path. 

Guernsey Path (2.2 miles, orange arrows)

Wander along the Charles River, see the Waban Arches, a historic landmark dating back to 1876, and walk through Wellesley College. The start of this trail is at the parking area along Winding River Road at the Needham border. The trail follows a sewer easement past the Guernsey and Susan Lee Memorial Sanctuaries to the Charles River. It then continues along the river, past Elm Bank across the river, under the Waban Arches, and along the Nehoiden Golf Course driveway (yield to golfers on the course) to Dover Road. It follows Dover Road to Washington Street, enters Wellesley College, and exits the campus at Weston Road and Central Street. The trail follows Weston Road across the railroad bridge and ends at the Crosstown Trail on Linden Street.

Esker Trail (0.8 mile loop, purple arrows)

Town Forest Map & Guide (PDF)

Walk along a steep, high esker deposited by the glaciers in the Town Forest. To get to the trail, follow the Charles River Path northbound from the Longfellow Pond parking lot to the top of the esker (0.1 mile). The loop trail starts here and is marked with purple arrows. Take trail to the right and ascend to the highest point on the esker (80 feet above the pond). Descend off the esker, circle around a drumlin and briefly join the Charles River Path. Turn left just before Longfellow Pond, ascend the esker, and continue to the start of the loop. 

Longfellow Pond Trail (0.8 mile loop, purple arrows)

Town Forest Map & Guide (PDF)

Explore the pond ecology and Town Forest on this popular trail. This trail starts at the Longfellow Pond parking lot off Oakland Street. The trail is a loop trail around the pond. Starting from the right side of the parking lot facing the pond, the trail gradually climbs to the old Hasting grave site where you get a good view of the pond. The trail continues around the backside of the pond, crosses over Rosemary Brook at the dam, passes the remains of the Metropolitan Ice Company's storage house, and continues along the pond back to the parking lot. 

Morses Pond Trail (1.2 mile loop, purple arrows)

Morses Pond Map & Guide (PDF)

Walk to the pond, see the Town Beach and explore the pine tree groves around the Town wells. The start of this loop trail is at the intersection of Turner Road and the Crosstown Trail at the entrance to the Town Beach. The trail follows the paved path for a short distance and takes trails to the beach parking lot where it turns left onto the beach service road. At the chain-link fence, the trail enters the beach (if gate is locked, retrace your route to the parking lot, turn left, and go past the water treatment facility to get back on the trail). The trail crosses the back of the beach, and continues along the edge of the pond. It climbs to the ridge of the gravel pit, runs along the edge, enters an extensive grove of tall pines, and completes the loop to the beginning of the trail.

Rockridge Pond Trail (0.4 miles, purple arrows)

Take a short, scenic trail along the shore of this picturesque pond. The trail starts at the parking area off Hundreds Circle. Facing the pond, the trail to the right runs along the pond to Cliff Road, and the trail to the left goes over the dam and ends at Rockridge Road.  

Sudbury Path (4.6 miles, blue arrows)

Follow the Sudbury Aqueduct from Needham to Wellesley College with less than a mile of on-road walking. This trail starts where the Sudbury Aqueduct crosses Hunnewell Street at the Needham town line. The trail follows the aqueduct past the Town Forest and joins Wellesley Avenue at the Wellesley Country Club. At the intersection of Forest Street and Wellesley Avenue the trail enters the Babson College Campus, meanders through the campus and joins a woodland path behind the Center for Executive Education. It then goes behind the Babson Sports Center to Olin College and follows the pipeline to a trail into the woods that leads back to the aqueduct. After crossing Great Plain Avenue, the trail runs along the aqueduct past the town RDF and continues to Beebe Meadows. It then goes along Benvenue Street where it rejoins the Sudbury Aqueduct just before Dover Road. The trail crosses the historic Waban Arches and ends at the Wellesley Centers for Women - Cheever House on Washington Street.

WCC Guernsey Sanctuary Trail (0.6 mile loop, purple arrows)

Walk along a woodland trail to Sabrina Lake, once part of William Baker's 1871 amusement park. Start at the entrance to the sanctuary, owned by the Wellesley Conservation Council (WCC), off the Guernsey Path near the parking area along Winding River Road. After crossing a small footbridge, a loop trail begins. Take the trail to the right. The trail runs along the sanctuary boundary in Needham to the lake, goes along the earthen dam back into Wellesley, and continues past a vernal pond to the loop starting point. 

Wellesley Grand Tour (10.8 mile loop, various arrows)

Wellesley Grand Tour Map (PDF)

A spectacular 10.8 mile loop around Wellesley's trails network which includes the Brook Path, Crosstown Trail, Charles River Path, Sudbury Path and Guernsey Path. Most of your travel will be on trails through woods or along aqueducts, with less than 3 miles along roads. Start on the Brook Path (pink arrows) at the High School, and walk eastbound to the Wellesley Hills Post Office. Turn right onto the Crosstown Trail (green arrows) and go eastbound to the Charles River. Turn right onto the Charles River Path (red arrows) and go southbound to the Sudbury Aqueduct. Turn right onto the Sudbury Path (blue arrows) and go westbound to the Waban Arches. Just before crossing the arches, take the feeder trail to the left down to the bottom of the arches, turn right onto the Guernsey Path (orange arrows) and go northbound to Fuller Brook. Turn right onto the Brook Path (pink arrows) and follow it back to the High School to complete the loop.