Outbound Collective logo

Oxford, Connecticut

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

Top Hiking Spots in and near Oxford

  • Cold Spring, New York

    Sugarloaf Mountain and Breakneck Ridge Loop

    4.7
    4.33 mi / 1562 ft gain
    The Breakneck Ridge to Sugar Loaf Loop gives rise to various bypasses that offer hikers moderate to advanced terrain and multiple rock scrambles. The loop entails a total elevation gain of 1,670 feet and a total distance of 5.5 miles. The start of the trail begins at the (white blazes) at the no...
    Read more
  • Cold Spring, New York

    Breakneck Ridge Loop

    5.0
    5.91 mi / 1526 ft gain
    This short but steep loop hike in Hudson Highlands State Park offers multiple panoramic views of the Hudson River along the way. Please note that only experienced hikers should attempt this route – although the hike seems short, the elevation gain and steep rocky scrambles offer serious technical...
    Read more
  • Beacon, New York

    Sugarloaf Mountain via Wilkinson Memorial Trail

    5.0
    2.15 mi / 820 ft gain
    Trail is currently closed. Get updates at parks.ny.gov.  Sugarloaf Mountain is part of the Hudson Highlands State Park, along with Breakneck Ridge, Bull Hill, and Mt Beacon. Though the views are just as impressive as its sister trails, it is never as crowded and it's one of my favorite spots in ...
    Read more
  • Beacon, New York

    Sunset Point - South Beacon Mountain Loop

    4.0
    8.92 mi / 2470 ft gain
    This loop hike form the Notch Trail northern trailhead on Route 9D.  There is enough parking at this trailhead for about 5-6 cars.  The Notch Trail is identified with blue trail markers.  It is well maintained and plenty of markers to guide your way.  This is important because there are m...
    Read more
  • Rye, New York

    Hike the Marshlands Conservancy Loop

    4.0
    1.55 mi / 125 ft gain
    Located along the Long Island Sound, this 147-acre conservancy is home to a plethora of different birds, including marsh wrens, seaside sparrows, and American woodcocks. The conservancy has 3 miles of trails, all easy to navigate. Starting out from the visitor's center, take the trail to the rig...
    Read more
  • 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
  • Beacon, New York

    Explore Long Dock and Dennings Point Parks

    4.0
    Long Dock and Dennings Point are two of the most popular parks in Beacon, that just so happen to be connected by a train track turned trail. Plenty of parking is available at Long Dock, and its a perfect spot to picnic, launch your kayak into the Hudson, or cast your line hoping to reel in the bi...
    Read more
  • East Lyme, Connecticut

    Hike Rocky Neck State Park Trail

    5.0
    2.5 mi / 141 ft gain
    Rocky Neck State Park Trail is a 2.5 mile loop hike where you may see beautiful wild flowers located near East Lyme, Connecticut.
    Read more
  • Cornwall, New York

    Storm King Mountain Loop

    4.5
    2.44 mi / 400 ft gain
    This is an easy, yet very rewarding hike with a lot of viewpoints on the way up. Technically you scale up two mountains, Butter Hill and Storm King, but most people just describe it as Storm King Mountain. This is a great hike for families with younger kids, those who don't have much time but wan...
    Read more
  • Cornwall, New York

    Hike the North Point Loop

    6.5 mi / 1400 ft gain
    There is three different trailheads to access the North Point Loop.  I chose the trailhead that would give me the longest hike.  That would be the Butter Hill parking area on Route 9W north.  From the parking lot, start on the connector trail designated with white markers.  Follow this for about ...
    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
  • 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
  • Cornwall-on-Hudson, New York

    Hike the Stillman - Bluebird Loop

    5.4 mi / 1200 ft gain
    This loop hike starts at the northern trailhead of the park where the Stillman Trail begins.  The parking area has enough space for only 6 or 7 cars.  Start off on a wide maintained carriage road.  After about a half mile, the Stillman Trail (yellow markers) breaks of to the left.  However, stay ...
    Read more
  • Highland Falls, New York

    Popolopen Torne

    4.5
    1.18 mi / 531 ft gain
    Popolopen Torne is a hidden gem in the Hudson Valley, a surprisingly unknown trail with a beautiful payoff and a far deeper meaning. A short hike to the top puts you at the foot of a memorial to those who have served their country, a pile of painted rocks carried up by those who want to pay their...
    Read more
  • Sheffield, Massachusetts

    Hike to Race Brook Falls

    4.0
    3.4 mi / 1174 ft gain
    Hiking along the Appalachian trail I made a detour in Mt Everett State reservation. About a 2.5 mile detour lead me down to a beautiful 100ft waterfall called Race Brook falls. The waterfall felt made me feel like i was in the tropical jungle in Hawaii. Adding to the beauty of the waterfall were ...
    Read more
  • Shelter Island, New York

    Hike through the Mashomack Nature Preserve

    10 mi
    Just a short ferry ride from the Hamptons, South Ferry Road is exactly where it sounds; very close to the South Ferry of Shelter Island. The parking lot of Mashomack Preserve is marked by a large sign. When you walk in, you'll see a large nature center. Sign in at a clipboard at the table out fro...
    Read more