New Milford, Connecticut
Looking for the best hiking in New Milford? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around New Milford. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near New Milford
-
Gardiner, New York
Hike the Dickie Barre, Peters Kill and Awosting Falls Loop
3.07.8 miThis loop hike takes you to Awosting Falls (65 ft.), as well as to great valley views along the ridge of Dickie Barre, and across Peters Kill, on the way.Start out on West Trapps Connector Trail (yellow blazes) at the east end of the West Trapps parking lot (get their early because the lot will ...Read more -
Gardiner, New York
Hike The Millbrook Mountain Ridge Trail
5.07 mi / 1400 ft gainWant to walk on the edge? visit Millbrook Mountain in the Catskills of NY. This loops hike follows the mountains ridge line most of the way to the summit with multiple viewpoints and cliff ledges to walk out on. This hike is recommended those in the area.Park at West Trapps Parking Lot and head ...Read more -
Gardiner, New York
Hike the Overcliff - Undercliff Road Loop
5.3 mi / 350 ft gainFrom the West Trapps parking lot ($15 for hikers), walk to the end of the parking lot and past a large kiosk. The trail connects the parking lot to the Overcliff Road/Undercliff Road junction. The loop can be done in either direction. I turned left on the Overcliff Road. This takes you behind...Read more -
Monroe, New York
Hike the Jessup/Highlands/Long Path Trails
7.8 mi / 500 ft gainThis trails starts at a small park in Woodbury called Gonzaga Park. Closed from mid-November to April, you are still able to park just outside the gate if that is the time of year you are hiking. Three different trail names share this path. The Jessup trail starts/end at Gonzaga Park and trave...Read more -
Glastonbury, Connecticut
Hike the Cotton Hollow Nature Preserve
5.03 miThere 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 -
Great Barrington, Massachusetts
Mt. Wilcox and Beartown Mountain Trail Loop
5.09.29 mi / 981 ft gainMt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.Read more -
Middlesex County, Connecticut
Hike to Glen Falls
5.00.75 miAccessing Glen Falls may be a little tricky at first. Parking will be very minimal, you will park on Grist Mill Ln. Hop onto the road and you will see the trail map on the left side. The adventure begins when you cross the street and go through the gate with the yellow blaze symbol. Keep followin...Read more -
Gardiner, New York
Gertrude's Nose
4.96.97 mi / 919 ft gainIt would be impossible to see all of Minnewaska’s beautiful spots in one day. Gertrude's Nose is, in my opinion, the best view in the entire park. Round trip, the hike is approximately 5 hours, and is a 7.5 mile trip. To get to the trailhead: Drive to the Minnewaska State Park entrance, pass the...Read more -
Gardiner, New York
Hike the Millbrook Mountain/Gertrude Nose loop
9 mi / 1700 ft gainThis great loop hike starts from the upper parking lot of Lake Minnewaska State Park. Walk towards Lake Minnewaska and once on that carriage road, turn left and follow the road to the to the opposite end of the lake. Along the way are great view points of the lake and several picnic areas for day...Read more -
Gardiner, New York
Lake Minnewaska Loop Trail
2.01 mi / 348 ft gainLake Minnewaska Loop Trail is a loop trail where you may see beautiful wildflowers located near Kerhonkson, New York.Read more -
Rye, New York
Hike the Marshlands Conservancy Loop
4.01.55 mi / 125 ft gainLocated 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 -
Great Barrington, Massachusetts
Hike Monument Mountain
4.02 mi / 720 ft gainAt 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under ...Read more -
Hudson, New York
High Falls Conservation Area Loop
1.41 mi / 194 ft gainHigh Falls Conservation Area Loop is a loop trail that takes you by a waterfall located near Philmont, New York.Read more -
Closter, New Jersey
Hike Alpine White Trail (Stateline Lookout)
5.05 mi / -520 ft gainStarting at about 520 feet, the White path takes you along the Stateline Lookout which is a small stone building overlooking the Hudson River. The initial descent is your average hike through the woods and across a couple of wooden bridges until you reach the Giant Steps. The Giant Steps take you...Read more -
Yonkers, New York
Run the Old Croton Aqueduct Trail
5.026.5 miThis trail traces the route of the Old Croton Aqueduct, which carried water to New York City between 1842 and 1955. Our recommended route starts near the Greystone Station in Yonkers, NY (Metro-North Hudson Line) and ends by the Scarborough Station, but you can easily modify your route – the enti...Read more -
Stockbridge, Massachusetts
Laura's Tower and Ice Glen
5.02.4 mi / 676 ft gainYou will park at the end of Park Street in Stockbridge, Massachusetts. From the parking are you will cross a beautiful bridge over the Housatonic River. The trail crosses railroad tracks and immediately begins to climb into the woods. You will reach a split in the trail, a left will take you...Read more