Westport, Connecticut
Looking for the best chillin in Westport? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Westport. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Chillin Spots in and near Westport
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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 -
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 -
Kent, Connecticut
Explore Kent Falls
5.00.75 mi / 250 ft gainEvery now and then you need a day to rest those sore muscle from all your recent adventures. The only issue is, you don't want to sit around inside, you want to be outside. Insert a trip to Kent Fall State Park. The perfect rest adventure day.Located 1 hour and 45 minutes north of New York City i...Read more -
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 -
New York, New York
Walk the George Washington Bridge at Sunset
3.00.9 miJoin the thousands of people who cross the GWB each day, but do it by foot! This is an easy walk with beautiful views of the New York City skyline. You will begin seeing signs for the bridge bike path at Ft. Washington St. & E. 177th St., which you follow for a few blocks until you begin asce...Read more -
Brooklyn, New York
Climb Outdoors at DUMBO Boulders (CLOSED)
5.0Practice bouldering at North America's largest outdoor rock climbing gym after work. Of course you aren't climbing mountains, but at least the view of the East River isn't too shabby! Enter at the corner of Adams St. and John St. and see the Manhattan Bridge above you. To your left is the new ...Read more -
Brooklyn, New York
Photograph Manhattan Bridge from Washington Street NYC
4.7Located in DUMBO this is seen as one of of the prime photography spots in NYC for good reason. Off the intersection of Washington Street and Water Street is a perfect view of the Manhattan Bridge sandwiched between two buildings. If you want to take it one step further you are able to get a close...Read more -
Brooklyn, New York
Photograph the Brooklyn Bridge
4.8Escaping the hustle and bustle of the city doesn't always require actually leaving the city. Hanging out next to the East River and focusing on photographing the Brooklyn Bridge can be just what you need to clear your head and get your fix for some outdoors time. This is a great spot to practice ...Read more -
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 -
New York, New York
Explore the South Street Seaport
5.0Get a feel for what New York was like in the 19th century at the Seaport! The Seaport boasts some of the oldest buildings and architecture in Manhattan, and the area continues to bustle today. The Seaport borders the Financial District and the East River - so there are lots of wonderful sights to...Read more -
Paterson, New Jersey
Explore the Great Falls of the Passaic River
3.2Getting 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
4.0Located 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 -
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 -
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 -
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