Greenwich, Connecticut
Looking for the best chillin in Greenwich? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Greenwich. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Chillin Spots in and near Greenwich
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Brooklyn, New York
Brooklyn Bridge Park
4.0The Brooklyn Bridge Park spans over a mile of waterfront and is an awesome location for being active or just relaxing outdoors without leaving the city. There is a ton of grassy space to set up a picnic and watch the sunset and many other options for fun - basketball courts, a carousel, roller sk...Read more -
Paterson, New Jersey
Explore the Great Falls of the Passaic River
3.3Getting to the Great Falls of the Passaic River is a relatively straight shot. It is located off exit 57B on Route 80 which is also accessible from highway 287. Parking is located on McBride Avenue across the street from the park's welcome center.Typically during autumn park rangers offer 45 to 1...Read more -
New York, New York
Battery Park
4.5Located at the Battery, the southern tip of Manhattan Island in New York City, facing New York Harbor. The Battery is named for the artillery batteries that were positioned there in the city's early years to protect the settlement behind them. There's also multiple transportation going on underne...Read more -
Philipstown, New York
Indian Brook Falls (CLOSED)
2.80.59 mi / 157 ft gainIndian Brook Falls is CLOSED as of 2022. Learn more at HighlandsCurrent.org. Take a short simple walk to a beautiful waterfall near the Constitution Marsh and Audubon Center. This waterfall is great spot for the whole family to take in its beauty. This is about as short a walk and as little eff...Read more -
Cedar Grove, New Jersey
Hike at Mills Reservation
4.72 mi / 200 ft gainMills Reservation is over 150 acres of wooded area located off of Normal Ave. near the Cedar Grove reservoir. Parking space is limited due to the small size but there is another hidden lot towards the back if you make a right out of the parking lot and then the first right turn onto Highland Ave....Read more -
Brooklyn, New York
Camp at Floyd Bennett Field
Brooklyn isn't just for the urban and trendy, its also for the people who love getting outside! Located just past the hustle and bustle of Brooklyn, Floyd Bennett Field is a National Recreation Area that features an Aviator Sports & Event Center (this was formerly an important NYC airport), t...Read more -
Ringwood, New Jersey
Explore Ringwood Manor State Park
5.01.3 miOn my way to the drive-in, I saw a sign for Ringwood Manor estate and wanted to adventure around. The parking is easy and the property was beautiful!As we walked through the estate, we found:a quaint tree foresta small cemetery with headstones hundreds of years olda river with a small waterfall ...Read more -
Staten Island, New York
Sunrise and Sunset from the Staten Island Ferry
5.0The Staten Island Ferry is a passenger ferry that runs between the boroughs of Manhattan and Staten Island. From the deck of the ferry, you will have a perfect view of The Statue of Liberty and Ellis Island. You'll see the skyscrapers and bridges of Lower Manhattan receding as you pull away and c...Read more -
Beacon, New York
Explore Long Dock and Dennings Point Parks
4.0Long 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 -
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 -
Patchogue, New York
Fire Island's Watch Hill
4.02 miIf departing from NYC, catch the early LIRR train from Penn Station (or Atlantic Terminal) towards Patchogue. You may have to transfer at both Jamaica & Babylon, but it's an easy hop across the platform. Trip will take approximately an hour and a half and cost around $15, Off Peak, each way. ...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 -
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 -
Cheshire, Connecticut
Hike to Roaring Brook Falls
5.01.2 mi / 377 ft gainArriving to the falls, parking is residential but don't worry everyone is friendly. Starting off the hike you will walk past a cool pond where you may be able to see some wildlife. Continuing on, you will follow the marked trail where it will take you further into the woods while gaining elevatio...Read more -
Dover Plains, New York
Hike Dover's Stone Church
4.5Dover Stone Church has been a beautiful and popular destination in the Hudson Valley for some time, and recently the park purchased a new parcel of land and added three trails through the nearby woods. But the gem of the park is, and always will be, the impressive cave with the creek and waterfal...Read more -
Washington, Connecticut
Hike the Mount Tom Tower Trail
1.3 mi / 337 ft gainStarting from the parking lot of Mt. Tom State Park, hop onto the Tower Trail (yellow trail) which leads more into the woods. During winter time, the trail may be slippery, please use your best judgement and always know your limits. Gaining about 300 feet in total elevation in approximately 1 mil...Read more