Top Adventures in Wellesley

  • Walk along Lake Waban

    This is a lake on Wellesley College Campus.  It is easy to get to from just about any direction. Just park and walk toward the lake, and there are paths that will take you there. The easiest place to park (pinned on the map) is just off Washington...

    3 miles

  • Hike the Wilson Mountain Reservation Trail

    This easy, well maintained trail has a little bit of everything you could need for a leisurely loop hike - bridges and streams, views of Boston, bird watching, and a dog-friendly policy (leash on).

    2 miles

  • Run the Arnold Arboretum Trail

    Park in the lot off of Arborway to access the trail. This place is gorgeous year round. The winter offers a quiet solitude, fall boasts bright colors, spring is the most beautiful as the flowers start to burst and cherry blossoms take over, and su...

    2.6 miles 150 ft gain

  • Run the Jamaica Pond and Victorian Jamaica Plain Loop

    Park in the Jamaica Pond parking area. You can go either direction on this loop trail, which is highly trafficked and dog-friendly. Keep a lookout for (and a respectful distance from) the wildlife that live here. The loop around Jamaica Pond itsel...

    1.5 miles 95 ft gain

  • Hike the Ashland Reservoir Trail

    Park in the lot on State Park Road (see map) to access the trail. It's a popular trail that is dog-friendly. Pay attention to the trail as at parts it is not well marked. 

    3.2 miles 68 ft gain

  • Hike around Walden Pond

    Park in the lot ($8 for MA residents) by Walden Pond to access the trail, and head out either direction on the loop around the pond. Trail is accessible from April-October. 

    1.69 miles 45 ft gain

  • Hike the Great Blue Hill Trail

    This is family-friendly hike takes you to nice views of Boston, after a moderately challenging stretch of elevation gain. Follow the blue markers along Great Blue Hill Trail to reach the observation tower. This is also a great spot for bird watchi...

    2.3 miles 550 ft gain

  • Hike the Ponkapoag Pond Trail

    Park at the end of Ponkapoag Trail Road to access the trail. Dog friendly, open year round. 

    3.82 miles 173 ft gain

  • Bike or Run on the Charles River Path

    The Charles River Path becomes a center of activity in Boston, especially during the summer, and you can run (or bike) it! It is a paved pathway that travels along both sides of the Charles River from the North End of the city to Allston and beyon...

    10 miles

  • Walk the Freedom Trail

    Park along the trail and then hop on. The Freedom Trail allows you to not only see the most beautiful parts of Boston (which is an absolutely gorgeous city) but you can learn some history too! Head off the trail a bit to explore the Charles River,...

    2.9 miles 121 ft gain

  • Bike the Minuteman Bikeway

    Park in the lot on Railroad Ave to access the Minuteman Bikeway from Bedford, MA. This 10-mile point-to-point paved path takes you through the scenic natural setting of Bedford. The bikeway is very popular, so expect to be sharing it with others, ...

    10 miles 177 ft gain

  • Hike the Pratt's Brook Conservation Area Loop

    Park in the small parking area right before the trailhead. *Notice this parking area is small and only fits about 3-4 cars so prepare to find street parking on a busy day. You can punch in the coordinates to a GPS if you need help finding it: 42.4...

    1.5 miles 85 ft gain

  • Nearby camping, hotels, and more

    • Northbridge, Massachusetts

      West Hill Park

      Overview On a quiet back road and across an old fieldstone bridge lies West Hill Park, where the West River widens to form a large, natural pool. The park and its many services and activities, incl...

    • Middleborough, Massachusetts

      Boston / Cape Cod Koa

    • Charlton, Massachusetts

      Buffumville Lake (Group Shelters)

      Overview In 1958 the U.S. Army Corps of Engineers built Buffumville Dam in Charlton, Massachusetts to provide flood risk management for downstream communities. Flood waters due to large amounts of ...

    • Litchfield, New Hampshire

      Normanton Farms

      This campsite is situated on a ridge that overlooks the Merrimack River, and is covered by bending silver maple trees. A perfect getaway for campers looking to explore the outdoors. Just a stone's ...

      From $100/night

    • Thompson, Connecticut

      West Thompson Lake Campground

      Overview West Thompson Lake Campground is located near the wooded shoreline of its namesake lake in northeastern Connecticut. The natural setting surrounding West Thompson Lake can be enjoyed year ...

    • Merrimack, New Hampshire

      Souhegan Serenade

      Souhegan Serenade is an auto accessible secluded campsite situated in a small clearing surrounded by mixed pine and hardwood alongside a beautiful river. The only things you will see from your site...

      From $135/night

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