Milton, Massachusetts

Top Spots in and near Milton

  • Quincy, Massachusetts

    Hike The Skyline Trail at Blue Hills

    4.0
    12.7 mi / 2542 ft gain
    Park 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...
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  • Milton, Massachusetts

    Houghton's Pond Recreation Area

    1.2 mi / 79 ft gain
    Houghton's Pond Recreation Area is a loop trail that takes you by the lake located near Milton, Massachusetts.
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  • Randolph, Massachusetts

    Hike the Ponkapoag Pond Trail

    4.0
    3.82 mi / 173 ft gain
    Park at the end of Ponkapoag Trail Road to access the trail. Dog friendly, open year round. 
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  • Boston, Massachusetts

    Run the Arnold Arboretum Trail

    5.0
    2.6 mi / 150 ft gain
    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 summer is overwhelmingly green. There are dozens of ...
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  • Boston, Massachusetts

    Run the Jamaica Pond and Victorian Jamaica Plain Loop

    5.0
    1.5 mi / 95 ft gain
    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 itself is 1.5 miles. The best part about running in thi...
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  • Boston, Massachusetts

    Freedom Trail

    4.7
    2.9 mi / 121 ft gain
    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, the waterfront near the aquarium and picturesque ...
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  • Cambridge, Massachusetts

    Bike or Run on the Charles River Path

    5.0
    10 mi
    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 beyond. There are several bridges along the way with pe...
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  • 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 ...
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  • Wellesley, Massachusetts

    Walk along Lake Waban

    3 mi
    Note: The campus is currently closed due to COVID-19 restrictions. 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 ju...
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  • Medford, Massachusetts

    Hike Southern Middlesex Fells Loop

    4.7
    3.5 mi / 756 ft gain
    Park in the parking area near Bellevue Pond. There are multiple entrances to the reservation (some closer to the reservoir itself than others). I have spent days in there hiking around and never seeing the water and there are days when I just hiked right in to the water and sat and enjoyed it. Th...
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  • Norwell, Massachusetts

    Hike the Norris Reservation Loop

    2.4 mi / 60 ft gain
    Choose from multiple trails in Norris that offer beautiful views of the the North river and marshland. Great spot to do some trail running through the woods and see the river too. There is also a pond a short distance from the parking lot that offers a great fishing spot with a picnic table nearb...
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  • Hanson, Massachusetts

    Burrage Pond Indian Trail

    5.0
    3.39 mi / 194 ft gain
    Burrage Pond Indian Trail is an out-and-back trail where you may see beautiful wildflowers located near Hanson, Massachusetts.
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  • Concord, Massachusetts

    Hike around Walden Pond

    4.5
    1.69 mi / 45 ft gain
    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. 
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  • Ashland, Massachusetts

    Hike the Ashland Reservoir Trail

    5.0
    3.2 mi / 68 ft gain
    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. 
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  • Acton, Massachusetts

    Hike the Pratt's Brook Conservation Area Loop

    4.0
    1.5 mi / 85 ft gain
    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: 42.4545482, -71.4358192.  The loop is very diverse wit...
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  • Marlborough, Massachusetts

    Hemingway Street Trail

    1.73 mi / 197 ft gain
    Hemingway Street Trail is an out-and-back trail that provides a good opportunity to view wildlife located near Marlborough, Massachusetts.
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Camping and Lodging in Milton

Boston / Cape Cod KOA Holiday
Middleborough, Massachusetts

Boston / Cape Cod KOA Holiday

West Hill Park
Northbridge, Massachusetts

West Hill Park

Buffumville Lake (Group Shelters)
Charlton, Massachusetts

Buffumville Lake (Group Shelters)

West Thompson Lake Campground
Thompson, Connecticut

West Thompson Lake Campground

Guides, Insights and Stories from Milton

Experience Cape Cod - Dune Shack Trail, Provincetown

Experience Cape Cod - Dune Shack Trail, Provincetown

Shaun Logan

 5 Tips for Finding Beautiful Fall Foliage in Massachusetts

5 Tips for Finding Beautiful Fall Foliage in Massachusetts

Gustavo Quiros