Southampton, New York
Looking for the best hiking in Southampton? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Southampton. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Southampton
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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 -
Montauk, New York
Climb the Bluffs of Shadmoor State Park
1.2 mi / 100 ft gainI've never actually been into the Shadmoor State Park, but you can climb up and onto the bluffs from the beach easily; well kind of easily.Most of the parking lots along the beach require Hamptons residency tags, so you can't park right next to beach entrances... bummer. We typically park along ...Read more -
Montauk, New York
Stroll along the Montauk Point Lighthouse Cliff Walk
4.51 miThe Montauk Point Lighthouse is one of the main attractions of "The End" of Long Island, but I've only ever walked around it on the cliff walk.When you get to the lighthouse, you can park in the parking lot (depending on when you go there may be a $8 fee). Right along the edge overlooking the wa...Read more -
East Lyme, Connecticut
Hike Rocky Neck State Park Trail
5.02.5 mi / 141 ft gainRocky Neck State Park Trail is a 2.5 mile loop hike where you may see beautiful wild flowers located near East Lyme, Connecticut.Read more -
Patchogue, New York
Camp at 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 -
Groton, Connecticut
Hike Bluff Point State Park Eastern Loop
4.54.3 mi / 344 ft gainBluff Point State Park Eastern Loop is a 4.3 mile loop hike where you may see beautiful wild flowers located near Groton, Connecticut.Read more -
Groton, Connecticut
Hike Haley Farm Loop
5.02.7 mi / 193 ft gainHaley Farm Loop is a 2.7 mile loop hike that takes you past wildlife located near Groton, Connecticut.Read more -
Groton, Connecticut
Hike Sheep Farm
3.01 mi / 91 ft gainSheep Farm is a 1 mile loop hike that takes you by a waterfall located near Groton, Connecticut.Read more -
Stonington, Connecticut
Hike Denison Pequotsepos Nature Center Trail
5.01.7 mi / 72 ft gainDenison Pequotsepos Nature Center Trail is a 1.7 mile loop hike that takes you by a river located near Mystic, Connecticut.Read more -
Westerly, Rhode Island
Napatree Point Conservation Area Trail
4.03.19 mi / 82 ft gainNapatree Point Conservation Area Trail is a loop trail that takes you past scenic surroundings located near Westerly, Rhode Island.Read more -
East Haddam, Connecticut
Explore Chapman Falls in Devil's Hopyard SP
4.0If you map to Chapman Falls in East Haddam, CT, you will be brought to a parking lot opposite from the waterfall in Devil's Hopyard, a beautiful Connecticut state park. Once there, it's only a few minute walk down a very clear trail to the base of the 60 foot falls. There's plenty of room to set ...Read more -
Stonington, Connecticut
Hike River Road
4.03.9 mi / 55 ft gainRiver Road is a 3.9 mile point-to-point hike that takes you by a river located near Mystic, Connecticut.Read more -
Hamden, Connecticut
Boulder & Free Climb off the Blue Trail In Sleeping Giant SP
Sleeping Giant State Park does not just have great hiking, it also has great climbing and bouldering. Pick up the blue trail starting at the backside of the visitor center. This trail climbs pretty steadily but take note that as you hike up the cliff below you is a great spot to checkout for boul...Read more -
Hamden, Connecticut
Hike the Tower Trail to the Blue Trail at Sleeping Giant SP
5.03 mi / 518 ft gainSleeping Giant State Park is a place very close to my heart. I spent 4 years right across the street at Quinnipiac University and have hiked “The Giant” more times then I can count and at all different hours. There are a few different trails you can explore but my favorite one is up to the cliffs...Read more -
Hamden, Connecticut
Hike the Mill River Trail to the Blue Trail at Sleeping Giant SP
5.03 mi / 518 ft gainSince I was a child, I’ve always enjoyed hiking the Giant. As Connecticut parks go, this terrain is some of the most challenging (and unfortunately, the most dangerous) in the state. The actual ridge is approximately 2.75 miles long by 1.75 miles wide, and offers approximately 24 miles of hiking ...Read more -
North Stonington, Connecticut
Hike Narragansett Trail
4.010.7 mi / 1 ft gainNarragansett Trail is a 10.7 mile point-to-point hike that takes you by a lake located near North Stonington, Connecticut.Read more