Florida, Massachusetts

Looking for the best hiking in Florida? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Florida. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Hiking Spots in and near Florida

  • Savoy, Massachusetts

    Tannery Falls Loop

    0.54 mi / 135 ft gain
    The hike to Tannery Falls may be a little confusing, I'll clear it up for you before you even go there! To get to The falls you will travel down a dirt road that isn't very well maintained during the winter. As you keep driving down the dirt road you will notice a pond , which means you are almos...
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  • North Adams, Massachusetts

    The Cascades Trail

    4.3
    1.97 mi / 315 ft gain
    The Cascades Trail is an out-and-back trail that takes you by a waterfall located near North Adams, Massachusetts.
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  • Williamstown, Massachusetts

    Hike the March Cataract Falls Trail

    4.0
    2.2 mi / 511 ft gain
    Park at the Junction of Sperry Rd and Rockwell Rd. To get to the trailhead, hike along Sperry Road for about 30 minutes. (Not to the end of the road, see map below.) Then hike along the March Cataract Trail, an out-and-back. You can bring dogs on leash. The trail is short but steep in some parts ...
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  • Williamstown, Massachusetts

    Mount Greylock via Money Brook Trail

    9.57 mi / 2849.96 ft gain
    Park in the parking lot on Hopper Rd. Walk to the end of the road where you will find the Hopper Trailhead. Take the right fork. The Money Brook trail will take you to a waterfall, the Mt. Greylock summit, and back to the end of Hopper Rd. The trail is long but worth the hike, exploring parts of ...
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  • Wilmington, Vermont

    Ward’s Cove at Harriman Reservoir

    Harriman Reservoir — also known as Whitingham Lake — is one of Vermont's largest bodies of water, stretching over 2,000 acres through the hills of Wilmington and Whitingham in the southern Green Mountains. Ward's Cove is one of the reservoir's quieter access points, offering a sheltered launch ...
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  • Woodford, Vermont

    Woodford State Park Loop

    5.0
    2.41 mi / 203 ft gain
    A great loop for the summer, Woodford is also amazing when winter winter comes to the State Park. It also comes earlier than just about anywhere else in Southern Vermont. At 2,400 feet above sea level, this is an easy spot to find winter without spending a fortune at the local ski resorts. Woodfo...
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  • Wilmington, Vermont

    Mount Olga Fire Tower Loop

    2.25 mi / 667.32 ft gain
    Tucked along Route 9 in Wilmington, Vermont, Molly Stark State Park is home to one of the most satisfying short hikes in the southern Green Mountains: the climb to the Mount Olga fire tower. At just 1.8 miles as a loop, it punches well above its weight — rewarding hikers with a genuine fire tow...
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  • Bennington, Vermont

    The Mile-Around Woods

    5.0
    1.33 mi / 243 ft gain
    The Mile-Around Woods in Bennington, Vermont, offers a moderate hiking trail that spans approximately 1.33 miles. The trail is circular, providing a continuous path through the woods. The terrain is varied, with some flat sections and others that are slightly hilly, making it suitable for interme...
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  • Cropseyville, New York

    Hike Dickinson Hill Fire Tower

    4.5
    3 mi / 200 ft gain
    Once you drive onto N. Long Pond Road you will follow it appproximately 1.5 miles to the end. From the parking you can take the short walk back on the road to the start of the trail. The trail is actually a rough Fire Tower Road. You will follow this for about 1.3 miles. Here you will see a se...
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  • Deerfield, Massachusetts

    South Sugarloaf Trail

    1.48 mi / 404 ft gain
    South Sugarloaf Trail is a loop trail that takes you by a river located near South Deerfield, Massachusetts.
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  • Shaftsbury, Vermont

    Lake Shaftsbury Loop

    4.0
    1.39 mi / 160.98 ft gain
    Lake Shaftsbury State Park is a small park in Southern Vermont between Bennington and Manchester. It is well-loved by locals as swimming spot in the summer, especially for families with kids.  Less well known is the nature trail that meanders around the perimeter of the lake. While only a mile in...
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  • East Nassau, New York

    Kinderhook Creek

    5.0
    1.62 mi / 308 ft gain
    Kinderhook Creek is a loop trail that takes you by a river located near Stephentown, New York.
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  • Erving, Massachusetts

    Rattlesnake Loop to Red Trail

    1.97 mi / 676 ft gain
    Rattlesnake Loop to Red Trail is a loop trail that provides a good opportunity to view wildlife located near Erving, Massachusetts.
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  • Stockbridge, Massachusetts

    Laura's Tower and Ice Glen

    5.0
    2.4 mi / 676 ft gain
    You will park at the end of Park Street in Stockbridge, Massachusetts.  From the parking are you will cross a beautiful bridge over the Housatonic River.  The trail crosses railroad tracks and immediately begins to climb into the woods.  You will reach a split in the trail, a left will take you...
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  • Jamaica, Vermont

    Hamilton Falls

    3.5
    6.51 mi / 1431.32 ft gain
    The hike to Hamilton Falls is an enjoyable 6.8 miles roundtrip voyage through gorgeous forest scenery alongside a babbling brook. Be sure to visit the upper and lower falls! This trail is kid and dog friendly, so why not bring both?! If you are visiting the falls in the summer, bring a towel and ...
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  • Great Barrington, Massachusetts

    Hike Monument Mountain

    4.0
    2 mi / 720 ft gain
    At 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under ...
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