Hiking Trails in Montauk – Grab your Group & Hike

Over the course of our three day Thanksgiving break various permutations of me and my group went on four different hikes in and around Montauk.  The off season in Montauk is our hiking season.  Residents of Montauk cheer when the tourists pack their bags and depart in September.  Weekend residents of Montauk cheer when the first frost arrives and the dreaded ticks bid their farewell for the season.  With the ticks at bay the trails of Montauk are back open for business.

My kids have grown up on these trails – first in baby Bjorns.  Later with short little legs they scrambled over the paths while their mouths formed the words “how much longer?”.  Now with their strong legs that are longer than mine, they are eager to scamper ahead with their friends.  They know every turn of our favorite paths, the best trees to climb, and the most fun large boulders to perch upon.


I love hiking with a group, moving in and out of various conversations as we amble through the woods and varied terrains and backdrops of Montauk.  Dogs are always underfoot and always so happy to be part of the group.


Here are my four of my favorite hikes in Montauk.  Some locals will bristle that I am sharing this with you, but I think we will all be better for it.  Nature makes people happy and hiking makes people feel more connected.  We all could use a bigger dose of both in our lives.

The Breakwall Path around the Lighthouse


I like to bring all first time visitors to this special spot so as to orient them to their location.  The fact that you are at the VERY END of a VERY Long Island becomes abundantly clear when you hop from rock to rock on this path.  Waves crash beneath you and the lighthouse is ever present as you meander around it’s circumference.  Usually there are surfers doing their Montauk thing and on the Thursday of Thanksgiving we were lucky to see multiple seals poking their heads out of the water.


The walk ends at a pretty spectacular beach and my group usually parks it here to sit on the rocks and gaze at the sea.  You can do this walk without paying the lighthouse fee (just amble down the path to the left of the lighthouse), but I would couple it with a tour through the lighthouse.  If you are feeling spry you can climb to the top of the lighthouse and also make time to visit it’s informative museum and well stocked gift shop.  The Lighthouse Grill, found just northwest of the lighthouse, is available for snacks and refreshments.  You can make a whole afternoon of this place.  Fun!

The Montauk Lighthouse is at the very tip of Long Island on Rte 27.  Just keep driving until you reach the end.  There is an $8.00 parking fee from 8am to 4pm daily in the Summer and on weekends in the Spring and Fall.  Thanksgiving weekend must be considered winter as access was FREE.

Big Reed Pond Path

Located on East Lake Drive, the path’s entrance is about 2 miles down the road on the right after you make the turn from Rte 27.  I discovered this path 15 years ago when my husband would go out for monster fishing trips and I was left behind with my deaf dog Addie.  We would go for marathon walks and explore together.  That’s when we discovered this path.  It is ideal for a group and fun for all ages.  There are trees to be climbed, little footbridges to cross and at the middle point of the 2.7 mile hike there is a platform that looks over the aptly named Big Reed Pond.


There are maps and lots of other tendril trails to explore, but the loop is our favorite.   Just follow the path to the left of the big sign in the parking lot and then meander along.  When in doubt veer right.

The Walking Dunes Hike

This is my kid’s absolute favorite hike.  They never say NO to a hike here which is refreshing.  But really what is not to love about a hike that reminds one of walking on the moon?  Having a dune at your disposal to jump and roll and climb on does not hurt this path’s particular appeal either.


Located at the end of Napeague Harbor Road just off of Highway 27 (it says it is in Montauk, but seems more like Amagansett to me) this hike’s start is clearly marked with a sign that says Walking Dune and an arrow pointing the way.  I know it should not be a big surprise when you then encounter the dune, but it always is.  I especially love bringing new people on this hike, like I did on Friday.   We had a gaggle of kids and a rather international crew assembled.  Introductions were made and new friendships were forged one sandy step at a time.


The kids NEVER once asked how much further and in fact were sad when we finally pulled the plug on the hike.

Seal Haul out Hike

I always try to bring visitors on this hike too.  It also can be coupled with a trip to The Lighthouse.  Park at Camp Hero Road and then cross Rte 27 and head back West to access the trailhead.  Follow the sign to Seal Haul Out and you will be treated to a fun path that twists and turns and offers a variety of flora to admire.  There are little rivers to cross and trees to be climbed and after about 30 minutes you emerge at the coastline.


A few more steps brings you to the seal haul out viewing area and if you are lucky there will be some seals.  It was high tide when we were there so seal viewing was limited, but we did see a head or two poking up in the distance.  Seals or no seals it is still a terrific hike and fun for the whole family.

These walks enable us to celebrate nature and be active together (an absolute necessity on this particular weekend of eating).  My friend Samira recently invited me and my son to hear Walter Isaacson, famed Historian and biographer, speak.  He has written about Steve Jobs, Albert Einstein, Benjamin Franklin, and most recently Leonardo Da Vinci.  When asked what commonality these geniuses shared, he observed that each man delved deeply into science, art AND nature.  I love this.  I think appreciating these three things is a vital part of living.  As parents we try to give our kids healthy bouts of exposure to all, but I am thinking the nature part is where we excel because of the hiking ethic we’ve developed in Montauk.  Montauk is a special place and we feel grateful for the abundance of opportunities we have to explore it.

I have some other favorite hikes but don’t want spill all my secrets… not just yet anyway. Grab Your Group and Hike!


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2 Responses

  1. How many days would you recommend in off-season (early April)? I like jogging on the beach and going for trail hikes as well as exploring shops.

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Please add my name to the waitlist!

Space does open up! When it does it’s often at the last minute. Will keep our fingers crossed. Would love to see you at this experience!