Maps, Guides & Descriptions
Interactive Trails Map
MapWellesley Trails Site
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Trails Network Maps and Guide
Woodland Trail Maps and Guides
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)
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 (2.4 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 goes through Hunnewell Fields to Rice St, along the Paine Street sidewalk, then to boardwalks crossing the Caroline Brook and wetlands. It continues along the Caroline Brook to Phillip Park and ends at the Washington Street and Maugus Avenue map house across from Elm Park. 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)
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 (3.5 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 (6.2 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 Cochituate Aqueduct Trail enters Wellesley. After crossing Overbrook Drive, cross Route 9 by going left to the Lexington Road traffic light, then right on the sidewalk. Left onto Dale St. and right onto driveway to the pump station. Go up steps in back of the building 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.
Esker Trail (0.8 mile loop, purple arrows)
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.
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.
Hundreds Path (1.4 miles, yellow arrows)
The Hundreds Path connects our trails network from the Crosstown Trail at Brown Park to the Weston trails network at Carisbrooke Reservation. From Brown Park on Colburn Road, follow the trail along the edge of the ballfield, and turn left at the gap in the fence before the playground. Take an immediate right along the Garden Close Condominiums’ driveway and exit to Garden Road. Follow Lanark and Rockridge Roads to the Rockridge Pond trailhead, and take a scenic trail along the pond to the parking area. Turn left onto Hundreds Circle for a short distance, and follow Ledgeways and White Oak Road to the Carisbrooke Reservation trailhead. The trail runs along the south branch of Cold Stream Brook to the parking area, and continues along the trail to the Weston town line. From here, take one of the three trails through the George and Nancy Bates Woods to Weston Trails.
Longfellow Pond Trail (0.8 mile loop, purple arrows)
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)
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.
North 40 Trail (1.0 miles, purple arrows)
The start of this loop trail is on Turner Road just off Weston Road at the stone dust path trailhead. Take the left trail to the boardwalk constructed in 2019 and see the vernal pool, then continue on the boardwalk to the Weston Road Community Gardens. Right on the garden road and shortly reenter the woods. The trail winds through a mixture of deciduous and evergreen trees and scrub growth on old farmland, and connects to the Crosstown Trail near the Weston Road and Linden Street parking area. After walking along the Crosstown Trail for about 5 minutes, take the trail to the right to the pine grove and back to the Turner Road trailhead.
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.
WCLT 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 Land Trust (WCLT), 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)
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, parks, 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.