New York, New York
Looking for the best chillin in New York? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around New York. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Chillin Spots in and near New York
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Stamford, Connecticut
Hike Cove Island Park Loop Trail
5.01.1 mi / 3 ft gainThis trail is accessible year round and features water views of the Long Island Sound with beach access. The trail is a popular spot for walking, biking, fishing, and even bird watching. But if you’re not quite in the mood to get your steps in, you can use the small beach to sit and chat with a f...Read more -
89 Van Orden Road, New Jersey
Hike the Hank's Pond Loop
7 mi / 500 ft gainHank's Pond loop can be accessed from the south at the corner of Clinton road and Van Orden road or from the north, parking at the lot on Stephens road. I hiked from the south on this trip. Follow the wide trail known as Hank's East trail marked with white blazes. Soon you will reach a trail c...Read more -
West Milford, New Jersey
Hike the Terrace Pond North - South Loop
10.7 mi / 1200 ft gainFrom Warwick Road, parking at the northernmost road side parking area, cross the road, and the Terrace Pond North trail (marked with blue blazes) begins as a steady climb until you gain a ridge that offers some great views for several miles. Eventually, you'll reach a power line where you turn ri...Read more -
Washington Township, New Jersey
Hike Hacklebarney State Park's Trout Brook Riverbanks
5.0This is a relatively easy hike through Hacklebarney State Park that is great for families with younger children, rock scrambling, photography, and just hanging out in nature. There are two different ways to explore Hacklebarney, either by staying on the packed gravel path or by following the bank...Read more -
Warwick, New York
Enjoy a Film at the Historic Warwick Drive-In
Take a trip back in time at the Warwick Drive-In and watch a feature film on the big screen. The Drive-In shows movies just in theaters and older films with three different screens / options to chose from. The theater sells tickets for both one movie and for double features, i.e. watch two movies...Read more -
Califon, New Jersey
Bike the Columbia Trail: Califon to High Bridge
There are multiple places to pick up the Columbia Trail (High Bridge, Califon, Long Valley, Flanders) but this post is for biking or running from Califon to High Bridge and back. The best place to park is at the old town railroad station on, of course, Railroad Ave. You will be able to see the en...Read more -
Cold Spring, New York
Photograph Indian Brook Falls
2.8This is about as short a walk and as little effort as you can put in for a beautiful waterfall. You can barely call it a hike, but I'll list it as such since you do walk through the woods for 5 minutes. The trail is extremely well built, and is pretty easily accessible through the winter.The trai...Read more -
Califon, New Jersey
Explore the Ken Lockwood Gorge
4.3One of New Jerseys best kept secrets has to be the Ken Lockwood Gorge. If you are looking for a relaxing, beautiful, and nature packs place then this area is perfect for you. You can access the gorge from two different points, either by driving down Raritan River Rd. and parking right before you ...Read more -
Princeton, New Jersey
Visit the Princeton Battlefield Park Suspension Bridge
4.80.5 miTo find this bridge, you essentially park at the Princeton Battlefield Park and walk all the way down towards the woods (you'll pass an old house if you're going the right way). When you enter the woods there will be a tight trail but it will quickly open up. When it does, you want to take a left...Read more -
Hopewell, New Jersey
Hike through the Sourland Mountain Preserve
5.02.91 miThe Sourland Mountain Preserve stretches from Hunterdon County all the way into Somerset County. The trails referenced here are on the southwest side of the preserve in Hunterdon County. They are accessible from an on site parking lot at 233 Rileyville Road in Ringoes NJ.There are several trails ...Read more -
Bridgeport, Connecticut
Stroll around Fayerweather Island
0.5 miParking is at the end of Barnum Road in the Seaside Park. Though the lighthouse grounds are accessible the tower itself is not open to the public. To access the island you must walk across the breakwater. Please use caution as it is uneven footing and at times can be slippery. From the isla...Read more