Fairfield, Connecticut
Looking for the best chillin 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 Chillin Spots in and near Fairfield
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Brooklyn, New York
Kingsland Wildflowers
Kingsland Wildflowers is a rooftop meadow located atop Broadway Stages in Brooklyn’s Greenpoint neighborhood, offering 24,000 square feet of native plants like bee balm, purple aster, and wild strawberries. The green space, a collaboration between Alive Structures, New York City Audubon, and the ...Read more -
New York, New York
Top of the Rock
4.2There aren't any mountain peaks to summit in New York City, but the view from the top of the Rockefeller Building is the next best thing. You'll have to pay a few bucks ($29 to be exact) and deal with some tourists but you won't regret your decision once you're looking out over one of the most ic...Read more -
New York, New York
Run the Hudson River Greenway
4.318 mi / 212 ft gainTo get in both some sights and a workout, follow the Hudson River Greenway to views of the Statue of Liberty, the Chelsea Piers, and George Washington Bridge, to name a few. This easy-access run is best done in the early morning or early evening, to avoid pedestrian traffic and too much sun. Keep...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 -
Weehawken, New Jersey
Photograph the NYC Skyline from JFK Boulevard East
The Big Apple. NYC has arguably the best skyline in the world. So, if you are one of the millions of people visiting wouldn't you want to get some photos of the entire skyline to post on social media and show friend & family? Skip the boat and helicopter tour lines (although a cool experience...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 -
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
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 -
Shelter Island, New York
Hike through the Mashomack Nature Preserve
10 miJust a short ferry ride from the Hamptons, South Ferry Road is exactly where it sounds; very close to the South Ferry of Shelter Island. The parking lot of Mashomack Preserve is marked by a large sign. When you walk in, you'll see a large nature center. Sign in at a clipboard at the table out fro...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