We packed up and headed out to Montauk for the day, having heard mountains of goodness about the beach town near the Hamptons at the "end of the world" (which is really just one of the end-forks of Long Island, NY). While the rich and famous often take their private jets and helicopters, we poor people went by car on a beautiful fall day. The drive was easy, though the last hour or so was on one-lane roads and there was no room to pass, so I'm willing to bet that a summer weekend in traffic to get there would be enough to deter us from returning ever again.
We passed the Hamptons; men, women, and children were dressed to the nines at table-clothed restaurants lining the narrow main streets of town and we wondered if we'd made a mistake traveling in our surf shorts, tanktops, and beach hair, but we forged onward toward "the end."
I've got to say that coming over the hill that gives you a view of the ocean was a moment to remember: partly because of it's beauty and partly because it meant we would finally be able to get out of the car.
We drove through town, and continued onward, stopping at an overlook to take a few pictures. We went wandering on a tiny path there, where we saw some baby snakes crossing the trail and heard rustling in the leaves and bushes as we disturbed the peace of the area...we never found out where the path led...it was a long way to walk without knowing if there was a goal at the end worth reaching. Another girl who had gone ahead of us turned back and ran into us with the same conclusion. We abandoned ship and returned to the car onward to "the end."
Finally made it to the
Montauk Point Lighthouse! A cul-de-sac of sorts where you can pay $8.00 to park (unless you want to walk or bike since there is no parking allowed on the roadway). The free stuff: take pictures of the lighthouse from the parking lot or take the walking path to the left or right of the entrance to the lighthouse that will take you down to the beach around the gated museum grounds (about a 30 minute walk if you don't stop to enjoy the views and relax). Otherwise you can pay an additional fee of $10 per adult which allows you entrance to the gated park area, access to the indoor museum, and a ticket to climb to the top of the lighthouse. All in all you won't spend more than an hour inside the gates.
We were really lucky because we were there on a beautiful day. There were tons of boats off the coast but, since it was after Labor Day Weekend, the tourist count was low and there were no crowds. We wondered if it would have been more lively with more people?
Heading back to town, we veered off to check out
ditch plains where we heard the best surf is in Montauk. We were lucky to run into a local who guarded our vehicle from cops since we didn't have a sticker to park in the lot. He told us the waves were good. We were disappointed to find 1' waves and still a whole bunch of surfers in the water (biggest crowd we saw in all of Montauk), but it was a really chill beach and there was a little food truck called the Ditch Witch. I liked the vibe there more than anywhere else in Montauk that day.
It had already been hours since we left home base, and we were getting hungry. We headed back to town where, luckily, there is a huge free parking lot, which was pretty much empty. We walked to the beach looking for a restaurant on the water, but nothing in sight. This is pretty typical on Long Island; homes on the beach, commercial properties inland. As with the rest of our day to that point, it proved to be just a quiet fall day.
A local woman pointed us to the German restaurant and told us they had the best beer in town, but we wanted something with more beach vibe, so we walked into town where we had seen more shops and people while driving through. We were distracted from the main street by some music pumping from what eventually turned out to be a hotel pool, so we retraced our steps back to the main road and ended up at The Gig Shack, which is absolutely not a shack, and its prices were anything but shack-like but we can't complain because the pot of GigShack Mussels was both ginormous and delicious. I would definitely suggest sharing this between more than two people, especially if you plan to eat anything else. Our server was wonderful and brought us extra bread to soak up and scoop the chowder-like sauce. Mmmm. It was busy but not packed, they had surfing on TV and chill jams from the speakers, so I would say lunch was the highlight of our trip.
We stopped into a few of the shops in town but everything was really pricey. I'm not complaining, because we'd always heard about Montauk and the Hamptons being mad expensive and the playground for the wealthy, but somehow I was still surprised that the prices of everything were so inflated. A night in the hotel was going to cost us literally hundreds of dollars so we opted not to find a pet-sitter from the get-go and headed back west in time to enjoy the sunset during the long drive.
Overall Summary:
Montauk was a beach town-ish. Definitely would suggest the drive out there during the off-season but I'd like to return during the high season because I have a feeling we completely missed out on the reason that it gets all the hype. It would also be better to spend the time with friends who know the best places to go, since the typical online resources didn't really convince us of anything in particular. Taking surf gear (and making sure there were some bigger waves) would also inspire us to try again.
I'd like to stay over to see what the nightlife is like or just to make the long drive a little more worth it, but unless we were to rent someplace between a group or stay with friends locally, I doubt we would find it worth the money to spend the night. I couldn't find a single lodging option under $150 for the night...and again, it was after Labor Day Weekend.
Most of my insight changes if you're loaded...so if that's the case, please ignore me and go enjoy your quick, easy, and beautiful heli or plane ride down the coast, the overpriced food, beverage, clothing, and gear, by all means, but I think I'll stick with any of the other little beach towns that we passed along the entire Long Island Coast if I want another day trip.
The Gig Shack was delicious.
I'd love to hear comments or suggestions for a mulligan on this trip that would convince us otherwise. We really wanted to love Montauk as much as everyone who told us about it, we just didn't feel it. :-/
Heading back to town, we veered off to check out ditch plains where we heard the best surf is in Montauk. We were lucky to run into a local who guarded our vehicle from cops since we didn't have a sticker to park in the lot. He told us the waves were good. We were disappointed to find 1' waves and still a whole bunch of surfers in the water (biggest crowd we saw in all of Montauk), but it was a really chill beach and there was a little food truck called the Ditch Witch. I liked the vibe there more than anywhere else in Montauk that day.
The water at the beaches was exactly as one would imagine it would be,
warm enough to pee in and not notice a change in temperature, and clear enough
to see your own happy toes. I would also say something nice about the sand but
in reality it was very similar to other sands I’ve felt between my toes. 
After a week of discussing the merits of a wig with Maxwell
and eating fish tartare, waking up on the last day was not much fun, to say the
least. I just couldn’t understand why I was leaving. I had spent a week in
paradise, waving hello to the sun every morning, and now I was returning, not
very willingly, to the icy tundra that was New York. I wished I could have gone
back to being four years old so I could throw a big hissy fit and shed some of
the tears that had come back. These were not the tears of joy from earlier. Unfortunately, I had to keep my angst inside and leave a
vacation that was better than anything I could have imagined. 
