Fairfield, Connecticut
Looking for the best hiking in Fairfield? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Fairfield. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Fairfield
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Middletown, Connecticut
Explore Wadsworth Falls
5.00.25 miWhen it comes to exploring Wadsworth Falls its ease of access couldn't be better. As soon as you pull into the parking lot you hear the falls roaring. Take the quick walk to see the picturesque scenery.Facts about Wadsworth Falls:Height: 25ft tall and doubled in width Rock: Hampden Basalt -the ro...Read more -
Highland Falls, New York
Popolopen Torne
4.51.18 mi / 531 ft gainPopolopen 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 -
Southington, Connecticut
Hike the Crescent Lake & Metacomet Trail Loop
4.02.4 mi / 269 ft gainThe 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 -
Berlin, Connecticut
Hike the Ragged Mountain Memorial Preserve
4.55.5 mi / 560 ft gainRagged 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 -
Cold Spring, New York
Mt. Taurus (Bull Hill)
4.53.52 mi / 1375 ft gainMt. Taurus (or Bull Hill) is a short, family and dog friendly, hike just outside the town of Cold Spring, easily accessible by car or taking the train into town. It snakes along the edge of an old quarry that is just now being retaken by nature and provides lookouts towards the Hudson, other near...Read more -
Cold Spring, New York
Hike the Cornish/Brook/Notch/Washburn/Undercliff Loop
8 mi / 1500 ft gainThis loop is a great option to avoid crowds on the west side of the Washburn trail. Start at the same trailhead for the Washburn Trail. The Cornish Trail is on the left and there is an obvious sign at the trail split a few feet from the parking area. The Cornish Trail is an old road from about...Read more -
Cold Spring, New York
Hike the Washburn/Nelsonville/Undercliff Loop
7.2 mi / 2000 ft gainThis is a difficult loop hike that has several different starting points. I chose to start at the Washburn Trail Head, which is the lowest starting point you can select. Nearly on the Hudson River, the trail ascends immediately along a well maintained road designated by white disc markers. Aft...Read more -
Cold Spring, New York
Sugarloaf Mountain and Breakneck Ridge Loop
4.74.33 mi / 1562 ft gainThe 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
5.05.91 mi / 1526 ft gainThis 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
Hike Fishkill Ridge
Fishkill Ridge is a strenuous but rewarding hike, and one of the less known areas in the Hudson Valley. The parking area is at the very end of Sunnyside Road in Beacon, along with the information board at the trailhead. The red trail leaves the lot and will take you up to the first peak on the ri...Read more -
Beacon, New York
Hudson Highlands Overlook Trail
3.29 mi / 1017 ft gainHudson Highlands Overlook Trail is an out-and-back trail that takes you through a nice forest located near Beacon, New York.Read more -
Beacon, New York
Sugarloaf Mountain via Wilkinson Memorial Trail
5.02.15 mi / 820 ft gainTrail 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
4.08.92 mi / 2470 ft gainThis 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 -
Cornwall, New York
Storm King Mountain Loop
4.52.44 mi / 400 ft gainThis 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 gainThere 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 -
Beacon, New York
Hike the Scofield Ridge Loop
7.5 mi / 1850 ft gainThere are some great view points along this route. Start from the Mount Beacon Park trailhead parking area. This leads to the Casino Trail (red markers). The trail climbs steeply to some old ruins of a casino. Most of what remains is only the brick structure housing the mechanics for a trolle...Read more