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Jamaica, Vermont

Top Spots in and near Jamaica

  • 285 Salmon Hole Lane, Vermont

    Hike Hamilton Falls

    3.5
    6.8 mi / 889 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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  • Glen Road, Vermont

    Hike the Lye Brook Falls Trail

    4.0
    4.7 mi / 938 ft gain
    The Lye Brook Falls Trail is a 4.7 mile hike through scenic trails just outside of Manchester Center, Vermont. The trail is open year-round, but the best time to go is during spring blooms or to see the fall colors. This hike is family friendly and fun for all ages. Dogs are allowed on this trail...
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  • Woodford, Vermont

    Woodford State Park Loop

    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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  • Shaftsbury, Vermont

    Hike Around Lake Shaftsbury

    1.3 mi / 42 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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  • Dorset, Vermont

    Hike 'The Merck'

    4.0
    2.5 mi
    Of the 10 trails at The Merck, The Wildlife Trail is a great hike through the forest that offers you the best way to see wildlife, streams and tracks. You can do the whole hike as a loop in about 2-2 1/2 hours or shorten it up with some shortcuts if you just want a quick hike. Great for family ...
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  • Wallingford, Vermont

    Hike the White Rocks Ice Beds Trail

    1.6 mi / 180 ft gain
    This 1.6 mile round trip hike starts from the Ice Beds parking lot in the Green Mountain National Forest in Vermont.  The trailhead is close to the parking lot entrance, following the blue-blazed trail.  Be sure to read the signs, as the far trailhead is a hike to the cliffs, not the ice beds. Af...
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  • 368 Weathersfield Trail, Vermont

    Hike Mount Ascutney

    3.0
    5.2 mi / 2326 ft gain
    This route to the top of Mount Ascutney is completed via the Weathersfield Trail. This trail goes past gorgeous Cascade Falls - often frozen in the winter months. There is a great spot to eat lunch at the top of Mount Ascutney to the side of the hang glider landing. While the summit itself does n...
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  • Poultney, Vermont

    Camp on Mount St. Catherine

    5.0
    Looking for the best view in all of Poultney, Vermont? Look no further than Lake St. Catherine Mountain. Located within Deane's Nature Preserve, this fast and easy hike tops as one of the best views and camping spots for the little time and energy needed to reach the summit. Only 30-45 minutes fr...
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  • 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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  • Williamstown, Massachusetts

    Hike Mt. Greylock via Money Brook Trail

    9.7 mi / 3034 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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  • Jaffrey, New Hampshire

    Summit Mt. Monadnock via Marlboro Trail

    5.0
    4 mi / 2300 ft gain
    Start at the Marlboro Trailhead (you can enter this in Google maps) off Shaker Road. There's parking and porta-potty bathrooms. The trail is well-marked with white dashes/M marks all the way up. Once on trail, the initial 800 ft climb is through forested terrain with a few brooks and streams alon...
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  • Jaffrey, New Hampshire

    Hike MT Monadnock via White Arrow Trail

    4.3 mi / 1485 ft gain
    Arriving at the Old Toll Road/Halfway House Trail head you will have $5 entrance fee. Starting on the Old Toll road you'll find yourself walking on a gradual incline into the beautiful New Hampshire wilderness. Everything you see and smell is fresh and vibrant. Following the road for 1.1 miles yo...
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  • Mendon, Vermont

    Hike to Killington Peak

    5.0
    3.4 mi
    The trail head (Bucklin Trail) is found a couple of miles up Wheelerville Road on the left. Wheerlerville is a dirt road that will be muddy in the spring and summer. The drive is long enough that you will think you did something wrong, but you haven't! the trail head will eventually pop up.The tr...
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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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  • Adams, Massachusetts

    Explore Bellevue Falls

    5.0
    When you reach the falls, you can cliff jump into a large swimming hole at the base. The best time to visit the falls is from April to November. Please note that dogs are not permitted here. Parking is at a cemetery, and the gates are open from 8am to 9pm. Use common sense before cliff jumping - ...
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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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Top Activities

Camping and Lodging in Jamaica

Winhall Brook
Londonderry, Vermont

Winhall Brook

Townshend Lake Day Use Area
Townshend, Vermont

Townshend Lake Day Use Area

Hapgood Pond
Peru, Vermont

Hapgood Pond

Brattleboro North KOA Journey
Putney, Vermont

Brattleboro North KOA Journey

Stoughton Pond Rec Area
Weathersfield, Vermont

Stoughton Pond Rec Area

Surry Mountain Lake Beach
Surry, New Hampshire

Surry Mountain Lake Beach

Guides, Insights and Stories from Jamaica

From NYC to the Slopes: A Weekend Ski Getaway

From NYC to the Slopes: A Weekend Ski Getaway

Sara Sheehy