Fairfield, Connecticut
Looking for the best hiking 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 Hiking Spots in and near Fairfield
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New York, New York
High Line
4.81.47 mi / 26 ft gainBuilt on a historic freight rail line and perched above the streets of Manhattan’s West Side, the High Line is a public park that features a green-lined walkway. Park hours depend on the season, although it never opens before 7am, so best to go for sunset. Although you may have some company on wa...Read more -
Sharon, Connecticut
Hike the Pine Knob Loop, Housatonic Meadows SP
5.02.5 mi / 770 ft gainThe Pine Knob loop is a 2.5 mile loop trail that takes you through beautiful thick woods filled with vistas, wild flowers and tons of wild life. You will start your adventure at the Pine Knob Trail head where you will be able to a Connecticut Appalachian trail guide. Pine Knob is a blue blaze ...Read more -
608 Ramapo Valley Road, New Jersey
Hike the Halifax Trail and Ruins in the Ramapo Valley Reservation
8.25 mi / 500 ft gainTo start, I recommend coming in the early morning or afternoon, as the parking lot fills up with people hiking, fishing or going for a walk with their family. I usually get my luckiest before 9. This park is as relaxing or exciting as you want to make it. Here is a good map to use/ print out. We ...Read more -
Brooklyn, New York
Brooklyn Bridge Walk via Brooklyn
4.71.12 mi / 0 ft gainWalking the Brooklyn Bridge from the Brooklyn side is a rewarding experience that blends history, architecture, and stunning views of New York City. Start your journey at the pedestrian entrance near Cadman Plaza, which is easily accessible by subway (Court Street or High Street stations). The br...Read more -
New York, New York
Brooklyn Bridge Walk
5.02.4 mi / 26 ft gainBrooklyn Bridge Walk is an out-and-back trail that takes you by a river located near New York City, New York.Read more -
Brooklyn, New York
Brooklyn Botanical Gardens
5.01.34 mi / 75 ft gainBrooklyn Botanical Gardens is a loop trail that takes you by a lake located near New York City, New York.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 -
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 -
Brooklyn, New York
Prospect Park Loop
4.73.65 mi / 223 ft gainThere are multiple places to enter Prospect Park. If you're looking for the main entrance to Prospect Park, it faces the stunning Soldiers' and Sailors' Arch in Grand Army Plaza. It is adjacent to the Brooklyn Botanical Garden, the flagship Brooklyn Public Library, and the Brooklyn Museum. As you...Read more