Boston, Massachusetts
Looking for the best chillin in Boston? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Boston. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Chillin Spots in and near Boston
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Boston, Massachusetts
Freedom Trail
4.72.9 mi / 121 ft gainPark 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, the waterfront near the aquarium and picturesque ...Read more -
Hull, Massachusetts
Explore the Bunkers at Fort Revere
Fort Revere is an 8-acre (3.2 ha) historic site situated on a small peninsula located in Hull, Massachusetts. It is situated on Telegraph Hill in Hull Village and contains the remains of two seacoast fortifications, one from the American Revolution and one that served 1898-1947. There are also a ...Read more -
Acton, Massachusetts
Hike the Pratt's Brook Conservation Area Loop
4.01.5 mi / 85 ft gainPark 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: 42.4545482, -71.4358192. The loop is very diverse wit...Read more -
Ipswich, Massachusetts
Photograph Castle Hill
4.0Castle Hill refers to either a 165-acre drumlin surrounded by sea and salt marsh or to the mansion that sits on the hill. Both are part of the 2,100-acre Crane Estate located on Argilla Road in Ipswich, Massachusetts.Take a walk through the public garden or down to the beach. Plenty of beautiful ...Read more -
Bolton, Massachusetts
Take a Stroll at Fyfeshire Conservation Area
1.0Fyfeshire is located in Bolton Massachusetts off "Wattaquadock Hill Road", near the "Fotini's Restaurant and Bar". The trailhead begins at a small parking area with a stone gate that says Fyfeshire Conservation area on a wood plank. Once you are in the conservation area you will see an opening in...Read more -
Taunton, Massachusetts
Kayak Lake Rico
4.3Lake Rico is a decent sized lake located in East Taunton, MA. You can spend hours out kayaking and exploring. From the parking lot the lake looks pretty small but there is an opening towards the back that leads into three larger sections. There is also an island in the back that is great for sett...Read more -
Groton, Massachusetts
Catch a Sunset at Gilbert Hill
5.01 miFrom Rt. I-495 Exit 31, Gibbert Hill has one of the greatest sunsets around Groton, MA area. You will see a lot of cows and even a castle. This is a very easy hike and a not so easy place to park, you have to leave you car on the side of the road, which is totally fine, I guess, it is easy.The wa...Read more -
Clinton, Massachusetts
Watch a Sunset at Wachusett Reservoir
4.5Wachusett Reservoir is located in central Massachusetts, northeast of Worcester. Easy location and parking, you can go anytime of the day and you won't be disappointed. The Reservoir is the second largest body of water in the State of Massachusetts, taking place in 5 cities around the area, West ...Read more -
Sutton, Massachusetts
Hike the Purgatory Chasm Trail
4.71 mi / 115 ft gainFor this 1-mile hike, you can park at the Purgatory Chasm Visitor Center. From there hit the trail and explore the unusual gap between the tall granite walls, which might be adorned with climbers. Great for all ages and dogs are welcome too. The trail is open March-November.Read more -
Provincetown, Massachusetts
Explore Hatches Harbor and Race Point
5.03.3 miHatches Harbor & Race Point Lighthouse trail is not super long or difficult. Pretty straight forward, at least up to Hatches Harbor. There is a small parking lot that fits about six cars off Province Lands Rd. I think we had a good amount of rain leading up to that day and the trail reflect...Read more -
Provincetown, Massachusetts
Dunes' Edge in Provincetown
Cape Cod, Massachusetts is full of campgrounds and dunes to explore, but the best of the two are located at the very end of the cape, around the areas of Truro and Provincetown. Travel to the very beginning (or end, depending on how you look at it) of historic U.S. Route 6, which spans from Prov...Read more