Denning, New York

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

Top Hiking Spots in and near Denning

  • Philipstown, New York

    Anthony's Nose via Appalachian Trail

    4.6
    1.95 mi / 682 ft gain
    Parking for the trail runs along both sides of 9D right up until the Bear Mountain Bridge. It can be busy on the weekends so just make sure you're as far off the road as you can and be especially careful unloading kids and dogs. The trailhead is located at approximately 41.322571, -73.975949 and ...
    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
  • Philipstown, New York

    Hike the Osborn Loop

    7.6 mi / 850 ft gain
    The Osborn Loop trail itself is not a loop.  It connects to a 2.5 mile section of the Appalachian Trail.  Hiking these together creates the loop.  Start at the trail head for the Appalachian Trail on South Mountain Pass Road.  There is parking for two or three cars.  Walk up the road a short dist...
    Read more
  • Bear Mountain, New York

    Hike Bald Mountain, Bear Mountain State Park

    4.7
    6.8 mi / 1080 ft gain
    From your starting point at the Bear Mountain Inn, go left along the Cornell Mine Trail. (This part can be a bit confusing, but go past the carousel to a shaded picnic area; that is where the trail starts.) You will go under a bridge and follow the trail until it takes a sharp left and descends t...
    Read more
  • Carmel Hamlet, New York

    Ninham Mountain Fire Tower

    5.0
    1.23 mi / 367 ft gain
    This is more of a stroll than a hike, which is nice because you can add it to another hike in the same day if you're in the area. From the dirt parking lot take the trail off to the right. Just stay straight and in about 15 minutes you'll see a huge fire tower (hard to miss). Feel free to climb a...
    Read more
  • Mount Washington, Massachusetts

    Bash Bish Falls

    4.3
    0.75 mi / 295 ft gain
    Bash Bish Falls is a spectacular 60-foot waterfall located on the Massachusetts-New York border in the southern Berkshires. This popular destination offers easy hiking access and stunning natural beauty, making it perfect for families and casual hikers. Parking Options Massachusetts Side: 0...
    Read more
  • Mount Washington, Massachusetts

    Mount Frissell and Brace Mountain Loop Trail

    5.08 mi / 807 ft gain
    Mount Frissell and Brace Mountain Loop Trail is a loop trail where you may see beautiful wildflowers located near South Egremont, Massachusetts.
    Read more
  • Salisbury, Connecticut

    Explore Riga Falls

    The best part of the adventure is finding this hidden gem also known as Riga Falls. Riga Falls is actually one of Connecticut's lesser known waterfalls, but arguably the most scenic. A helpful hint is that the waterfall lies beside dirt road, keep your ears open! I've already said too much, happy...
    Read more
  • Vernon Township, New Jersey

    Stairway to Heaven

    4.8
    6.8 mi / 1089 ft gain
    This popular hike starts out on the Appalachian Trail (AT, white blazes). You begin on a boardwalk that crosses over a marsh, then you leave the boardwalk and enter a forested area. At around 1.4 miles, follow a bicycle path, Canal Road, then turn right, cross over a bridge, and take a left throu...
    Read more
  • Cortlandt, New York

    Camp Smith Trail

    4.0
    5.92 mi / 1759 ft gain
    This approximately 3-hour hike borders the Hudson River, and is one of the best in Westchester County. Start off at the parking area at the Bear Mountain Tollhouse, or at a small parking area farther up Bear Mountain Road, if you want a slightly shorter hike. The trail is fairly steep in places, ...
    Read more
  • Mount Washington, Massachusetts

    Guilder Pond and Mount Washington Lookout Trail

    3.92 mi / 909 ft gain
    Guilder Pond and Mount Washington Lookout Trail is a loop trail that takes you by the lake located near Copake Falls, New York.
    Read more
  • Salisbury, Connecticut

    Bear Mountain Loop

    4.7
    6.05 mi / 1516 ft gain
    At 2,316 feet, Bear Mountain is the highest peak in Connecticut. The peak is about a half-mile south of the Massachusetts state line on the Appalachian Trail. The views are great. On a clear day you can see some of the peaks in southern New Hampshire. The remnants of a stone tower are on the summ...
    Read more
  • Voorheesville, New York

    Hike the Keleher Preserve Loop

    2.0
    3 mi / 1636 ft gain
    The historic preserve is operated by the Mohawk Hudson Land Conservancy, so trails are clearly marked and extremely well maintained. There are features of the original farm that the land was used for from the 18th Century, including hand-thrown stone walls and an old logging road that cuts throug...
    Read more