Chester, Massachusetts

Top Spots in and near Chester

  • 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...
    Read more
  • 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...
    Read more
  • Stanfordville, New York

    Explore Wethersfield Estate & Gardens

    The Wethersfield Estate is a beautiful estate and property located less than 2 hours north of New York City. The gardens are expansive and extremely beautiful, open to the public each day from noon to 5pm (COVID-19 hours). Additionally, there are trails for horseback rides, carriage rides, dog-wa...
    Read more
  • Washington, Connecticut

    Hike the Mount Tom Tower Trail

    1.3 mi / 337 ft gain
    Starting from the parking lot of Mt. Tom State Park, hop onto the Tower Trail (yellow trail) which leads more into the woods. During winter time, the trail may be slippery, please use your best judgement and always know your limits. Gaining about 300 feet in total elevation in approximately 1 mil...
    Read more
  • Kent, Connecticut

    Hike the Ridge Loop Trail, Macedonia Brook SP

    3.0
    For a quick weekend trip from Newport, RI, Macedonia Brook State Park had a lot to offer for its size. In three or four hours, with lunch, you can hike the 6.4 mile ridge trail and get some fresh air without having to hike on too busy of trails. The elevation gain is only around 700 ft, however, ...
    Read more
  • Southington, Connecticut

    Hike the Crescent Lake & Metacomet Trail Loop

    4.0
    2.4 mi / 269 ft gain
    The hike to view Crescent Lake is peaceful. You can either walk through the woods where you will be blessed with natures finest birds and wildlife or you can take the trail along the lake edge. Both are similar distances and lead to the same hill at the end! Once you get to the top take a left on...
    Read more
  • Washington, Connecticut

    Hike Meeker Trail

    3.3 mi / 639 ft gain
    Meeker Trail is a 3.3 mile out and back hike that takes you by a lake located near New Preston, Connecticut.
    Read more
  • Berlin, Connecticut

    Hike the Ragged Mountain Memorial Preserve

    4.5
    5.5 mi / 560 ft gain
    Ragged Mountain main loop is approximately 5.5 miles long, and is known for its expansive bare-rock vistas, vertical cliff faces, and scenic views overlooking cliff-side reservoirs and ponds.  The trail is rated moderate, with some flat stretches among the trees, mixed with some uneven rocky foot...
    Read more
  • Southington, Connecticut

    Rock Climb Ragged Mountain

    The main face of Ragged Mountain (elev. 761 feet) is home to a lot climbing in central Connecticut. It runs north-south for about 600 feet. Its max height of 100 feet. The crag is home to several rock climbing guides and schools. Routes range in difficultly from great for the beginner (5.3) to su...
    Read more
  • 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...
    Read more
  • Glastonbury, Connecticut

    Hike the Cotton Hollow Nature Preserve

    5.0
    3 mi
    There are two parking locations for Cotton Hollow, the location tagged in the directions is the shortest hike to the old gun powder mill. Suggestions when it comes to exploring the preserve are to stay on the trails, know your limits, and enjoy! There are swimming holes along the river, but swim ...
    Read more
  • Glastonbury, Connecticut

    Blackledge Falls

    4.0
    1.46 mi / 207 ft gain
    Although the park contains hiking trails, a pond and a streambelt, the primary draw of this parcel of land is the 25 foot waterfall. The falls flow varies depending on the volume of precipitation, from a trickle in the dry months to a three-pronged vertical drop after some consistent snow melt or...
    Read more
  • Dover Plains, New York

    Hike Dover's Stone Church

    4.5
    Dover Stone Church has been a beautiful and popular destination in the Hudson Valley for some time, and recently the park purchased a new parcel of land and added three trails through the nearby woods. But the gem of the park is, and always will be, the impressive cave with the creek and waterfal...
    Read more