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Town Trails

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We have 43 miles of trails in Welesley, and our trails network has 26 miles of marked trails with trail descriptions.  We have long trails that interconnect open spaces in different parts of town and shorter woodland trails that explore Wellesley's conservation lands.  All network trails are marked with color-coded arrow markers. Interconnecting trails have uniquely colored arrows, and woodland trail have purple arrows. Trail markers are mounted on trail posts, trees, telephone poles and lampposts.

Wellesley trails are part of the Charles River Link, a 16-mile, six-town regional trail extending from Newton to the Bay Circuit Trail in Medfield.

Be aware that we sometimes reroute, extend or modify trails as we enhance the network, and trail routes and descriptions may change.  Please see trails news for updates.

Trail Maps and Guides

In cooperation with the Network & Information Systems (NIS) Department, we have developed a set of trails maps covering the complete town and four areas with extensive trail systems.  The following maps and guides are available:

Wellesley Trails & Open Space Map - Town street map showing trails and open space locations.
Wellesley Trails Pamphlet
Boulder Brook Reservation, Kelly Memorial Park and Rocky Ledges Trails Pamphlet
Centennial Reservation, MassBay Community College and Maugus Hill Trails Pamphlet
Centennial Reservation, Self-Guided Nature Trail Brochure
Morses Pond, Cochituate Aqueduct and North 40 Trails Pamphlet
North 40 Trail Map
Town Forest, Longfellow Pond and Ollie Turner Park Trails Pamphlet
Wellesley Grand Tour - 10.3 mile loop using all the interconnecting paths

Copies of the Wellesley Trails and Open Space Map are available for purchase at the Town Clerk's Office (24"x18", $5; 36"x24", $10).  Trail pamphlets are available for free at the trailhead map houses and at the NRC office.  If you wish to print your own pamphlet, print the trail guide on one side of the paper and the trail map on the back, and fold in thirds.

Trail Descriptions

Beard Trail:  Follow a woodland trail through Ridge Hill Reservation along the Needham border. The start of this trail is at Beard Way off Grove St. 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 Rd. The trail then runs along Cartwright Rd. and ends at Beebe Meadow. Trail is marked with purple arrows.  Length of the trail is 1.1 miles.

Boulder Brook Reservation Trail: 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 Rd. 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. Trail is marked with purple arrows.  Round trip length of the trail is 1.6 miles, and the elevation gain is 140 feet. See Boulder Brook Reservation, Kelly Memorial Park and Rocky Ledges Trail Guide and Map for more details.

Brook Path: A pleasant walk on level and partially paved paths along the Caroline and Fuller Brooks through Fuller Brook Park. This trail parallels Washington St. from Wellesley Hills to Dover Rd. but avoids the congestion and traffic of the downtown area. The trail starts at Maugus Ave. and follows the Caroline Brook to Wellesley High School, where it joins Fuller Brook. It then runs along Fuller Brook, past the Hunnewell School, and ends across from the Nehoiden Golf Course. Trail is marked with pink arrows.  Length of the path is 2.3 miles.
New Trail Section at Hunnewell Fields:  Follow trail posts on newly marked section from Rice St to stone dust path in back of high school stadium.  

Carisbrooke Reservation Trail:  Explore the rocky outcrops near the source of Cold Stream Brook. The start of this loop trail is at the end of Glen Brook Rd., which is off Glen Rd. 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. Trail is marked with purple arrows.  Length of the trail is 0.5 mile.

Centennial Reservation:  Walk over rolling meadows and up Maugus Hill to view the Blue Hills. The trail starts at the Centennial Reservation parking lot off Oakland St. 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 Ave. At the top of Maugus Hill, the trail descends toward Wareland Rd. 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. Trail is marked with purple arrows.  Round trip length of the trail is 1.7 miles, and the elevation gain is 200 feet.  See Centennial Reservation, MassBay Community College and Maugus Hill Trail Guide and Map for more details. Also see the Self-Guided Nature Trail Brochure featuring 10 stations near Bezanson Pond.
Parking Lot Trail Notice: The parking lot at Centennial Reservation will be closed completely for the week of July 10, 2017 to allow for the reconstruction of the parking lot. As a reminder, parking is prohibited on both sides of Oakland Street.   Please plan to use other entrances to the reservation.

Charles River Path:  Explore the banks of the Charles River and climb eskers in the Town Forest. The trail starts along the Charles River at the Weston town line and follows the river along Boulevard Rd in Lower Falls.  It goes in back of the Waterstone complex to Washington St and then follows Washington St. 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/Rt.-128 to Ouellet Park. It runs along Cedar St., enters the Town Forest off Rt.-9 and proceeds over an esker to Longfellow Pond. It then crosses Oakland St. and climbs steep eskers along Rosemary Brook, ending at the Sudbury Aqueduct. Trail is marked with red arrows.  Length of the path is 3.2 miles.  See Town Forest, Longfellow Pond and Ollie Turner Park Trail Guide and Map for more details on the southern section of the trail.

Crosstown 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 Dr. to Rt. 9, crosses at the traffic light, and continues east on Rt. 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 St. and Weston Rd. The trail then runs along Linden St. and Crest Rd. to Post Office Square, goes behind Town Hall to the Duck Pond and Morton Park, and then along Washington and State Sts. to the Wellesley High School stadium parking lot. It continues along the Cochituate Aqueduct across Hunnewell Fields to Forest St., then proceeds along Washington St. and Woodlawn Ave., where it rejoins the Cochituate Aqueduct. The trail continues along the aqueduct past Indian Springs Park and the Warren Building to Walnut St. It then runs along Walnut St. to Cedar St., rejoins the aqueduct, and ends at the intersection with the Charles River Path. Trail is marked with green arrows.  Length of the trail is 5.9 miles.  For the western section, see Morses Pond, Cochituate Aqueduct, and North 40 Trail Guide and Map for more details.

Guernsey Path:  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 Rd. 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 Rd.  It follows Dover Rd. to Washington St., enters Wellesley College, and exits the campus at Weston Rd. and Central St.  The trail follows Weston Rd. across the railroad bridge and ends at the Crosstown Trail on Linden St.  Trail is marked with orange arrows.   Length of the path is 2.2 miles.

Esker Trail:  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. Length of the trail is 0.8 miles. See Town Forest, Longfellow Pond and Ollie Turner Park Trail Guide and Map for more details.

Longfellow Pond Trail:  Explore the pond ecology and Town Forest on this popular trail. This trail starts at the Longfellow Pond parking lot off Oakland St. 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 gravesite 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. Trail is marked with purple arrows.  Length of the loop trail is 0.8 mile. See Town Forest, Longfellow Pond and Ollie Turner Park Trail Guide and Map for more details.

Morses Pond Trail: 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 Rd. and the Crosstown Trail at the entrance to the Town Beach.  The trail follows the paved path to the beach parking lot and 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.  Trail is marked with purple arrows.  Roundtrip length of the trail is 1.2 miles.  See Morses Pond, Cochituate Aqueduct, and Wellesley College North Forty Trail Guide and Map for more details.

Rockridge Pond Trail:  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 Rd., and the trail to the left goes over the dam and ends at Rockridge Rd. Trail is marked with purple arrows.  Length of the trail is 0.4 mile.

Sudbury Path:  Follow the Sudbury Aqueduct for 4.6 miles from Needham to Wellesley College with less than a mile of on-road walking. This trail starts where the Sudbury Aqueduct crosses Hunnewell St. at the Needham town line. The trail follows the aqueduct past the Town Forest and joins Wellesley Ave. at the Wellesley Country Club. At the intersection of Forest St. and Wellesley Ave. 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 Ave., the trail runs along the aqueduct past the town RDF and continues to Beebe Meadows. It then goes along Benvenue St. where it rejoins the Sudbury Aqueduct just before Dover Rd. The trail crosses the historic Waban Arches and ends at the Wellesley Centers for Women - Cheever House on Washington St. Trail is marked with blue arrows.  Length of the trail is 4.6 miles.
Sudbury Path Trail Notice:  Work has started on restoring the Rosemary Brook syphon houses.  Temporary trail detours have been provided at Brookside Rd along Wellesley Ave and at Comeau St along the south side of the aqueduct.  This project is scheduled to be completed in the summer of 2017.

WCC Guernsey Sanctuary Trail:  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 Rd. 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. Trail is marked with purple arrows.  Roundtrip length of the trail is 0.6 mile.

Wellesley Grand Tour:  A spectacular 10.3 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 only 2.3 miles along roads.  Start on the Brook Path (pink arrows) at the High School, and walk eastbound to the Clock Tower in Wellesley Hills.  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. See Grand Tour map for complete route.

Suggested Walks

Our trail network provides walks for all ages and levels of experience.  There are fairly level trails along waterways, ponds, aqueducts and roads that are easy to walk, and there are woodland trails over rougher terrain with elevation gains that are more demanding.

Here are some suggested trails for different age groups and experience levels:

Easy:  Brook Path, Carisbrooke Reservation Trail, Guernsey Path, Longfellow Pond Trail, Beard Trail, Crosstown Trail from Weston Road along the aqueduct to Route 9 (1.4 miles) and from Woodlawn Avenue along the aqueduct to Walnut Street (1.2 miles),  Rockridge Pond Trail, WCC Guernsey Sanctuary Trail and Sudbury Path .

Harder:  Charles River Path, Boulder Brook Reservation Trail, Centennial Reservation Trail, Esker Trail, and Morses Pond Trail.

Kids:  Brook Path, Carisbrooke Reservation Trail, Guernsey Path, Boulder Brook Reservation Trail, Centennial Reservation Trail, Longfellow Pond Trail, Morses Pond Trail, Rockridge Pond Trail and WCC Guernsey Sanctuary Trail.

Long:  Crosstown Trail (5.9 miles, one way), Sudbury Path (4.6 miles, one way),  Wellesley Grand Tour (10.3 mile loop). and Charles River Link (a 16.5-mile regional trail, one way)

Trail Use Guidelines

-  All motorized use prohibited.
-  No littering or dumping.
-  No fires or smoking.
-  No camping.
-  No alcoholic beverages.
-  Fields are full of poison ivy, so stay on mowed trails.
-  Do not feed, approach or touch wildlife, including waterfowl.
-  Take personal protection measures to reduce your exposure to ticks and mosquito bites.
-  Abide by Town's restriction of no more than 2 dogs per person or 3 dogs with a permit.
-  Please pick up after your dog and properly dispose of the waste.  Thanks!

Additional Information

Brochures and maps describing trails, nature walks, parks, and open spaces are available free of charge at the Natural Resources Commission office located in the lower level of Town Hall.  Map and trail guide pamphlets are available at our map houses sprinkled along the trail system. If you would like a large copy of the Wellesley Trails and Open Space Map, you may purchase it at the Town Clerk's Office (24"x18", $5; 36"x24", $10).

Another good source is the book Walks in Wellesley: exploring open space and trails, published by the Wellesley Conservation Council, Wellesley's private land trust.  The book was recently updated (c2010) and is on sale at the NRC Office and available at the Wellesley Library (Call No. 917.44 Walks).  Also see the Wellesley Conservation Council website for more information about their history, sanctuaries and programs, and how to become a member.

Information about Wellesley's Parks, Reservations and Public Open Space is contained in a publication issued by the Department of Public Works, Park and Tree Division.  It was published in 1990 and is slightly out of date, but a good reference containing interesting historical and descriptive information about the Town's open spaces.

Wellesley Town Hall  525 Washington St., Wellesley, MA 02482
Phone: (781) 431-1019
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