Rutland, Massachusetts
Looking for the best hiking in Rutland? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Rutland. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Rutland
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Milton, Massachusetts
Houghton's Pond Recreation Area
1.2 mi / 79 ft gainHoughton's Pond Recreation Area is a loop trail that takes you by the lake located near Milton, Massachusetts.Read more -
Randolph, Massachusetts
Hike the Ponkapoag Pond Trail
4.03.82 mi / 173 ft gainPark at the end of Ponkapoag Trail Road to access the trail. Dog friendly, open year round.Read more -
Plainfield, Connecticut
Hike Sugar Brook Loop Trail
4.03.3 mi / 200 ft gainSugar Brook Loop Trail is a 3.3 mile loop hike that takes you by a river located near Plainfield, Connecticut.Read more -
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 -
Providence, Rhode Island
Neutaconkanut Loop
5.01.49 mi / 171 ft gainTo enter the park, you first have to go through a field and past a baseball park. Next, you will see a high slope, you can either enter the trails through here or the stairs at the side. Some of the trails are overgrown and may have ticks or poison ivy so be careful. This place is good for kids a...Read more -
Quincy, Massachusetts
Hike The Skyline Trail at Blue Hills
4.012.7 mi / 2542 ft gainPark in the lot across from Batterymarch Rd off of Willard St. Access the Skyline trail from here, it is marked blue. Follow the signs. The trails in Blue Hills are perfect for training for backpacking because they are so steep and rocky. I would fill up a big pack and take the skyline trail up t...Read more