Things To Do in Montauk (Besides Laying Out By The Pool)

May 22, 2018

Montauk Travel Guide

I was itching to have one last beach hurrah before I’m on baby lockdown and have a temporary travel ban imposed on me. So after convincing hubby that I was unlikely to go into labor at 34-weeks (I looked up the statistic and I believe the likelihood statistically is at 5%) we decided to go to have a weekend getaway to Montauk a couple of weekends ago. On calendar the timing seemed perfect: it was the beginning of the season and rates were cheap, I was early enough in my pregnancy that I’m unlikely to deliver, and it happened to coincide with our wedding anniversary.

Well as Murphy’s law would have it, what can go wrong will go wrong. The week was sunny and beautiful and the weather literally turned ugly the evening we got there. Who knew I needed to pack for sweaters and thicker jackets for a beach trip in May? Unwilling to have a little inclement weather ruin our weekend, we decide to make the best out of it. And hey, now I have a plethora of suggestion of things to do in Montauk besides the obvious of laying out by the pool and the beach. Read on to check out my full list.


  • Montauk Light House: There is lots of views and history to be had here, so it’s definitely not a place you want to miss. Be sure to come early as they close at 4:30pm.
  • Camp Hero Bluff: Located “next door” to the lighthouse, this spot offers romantic walks and stunning vistas of the lighthouse. Another reason for you to give yourself plenty of time is because this place also close at dusk. So maybe visit the lighthouse first, then check out this spot for a second photo opp?
  • Block Island: Block Island is totally doable as a day trip from Montauk as there are daily ferries that go to and from. Might be a great addition of something to do if you’re in Montauk for longer than 3 days. I wish we had the foresight to do this but alas we didn’t plan well and woke up too late to catch the ferry out. It’s for sure something that’s on my to do list for the next trip to Montauk.



  • Duryea Lobster Deck: I was a bit skeptical about this place at first since they have less than four star rating on Yelp (I’m a bit of a Yelp addict). But it came highly recommended by a co-worker, so I decided to go anyway. I’m glad I did because it was such a cute restaurant with great views and clam chowder that hit the spot on a cold rainy day. I have to caveat that the restaurant is a bit pricey. Google has it listed as $$, but I think the food prices warrant more of a $$$ rating.
  • Tauk at Trail’s End: Blame it on us waking up late and eating lunch late, but we always ended up eating dinner at 9 or later. This restaurant was one of the few places within walking distance of our hotel that opens late. Portions are HUGE! Hubby and I shared a plate of fish and chips and sauteed veggies, and we were plenty full afterwards. Oh and they also have live music on most days.
  • 668 The Gig Shack: another great place that opens for dinner and drinks late. They also have live music which I believe features the same artist as Tauk at Trail’s End. Seems like he just takes turn between the two restaurants, which I did not mind because he was fabulous entertainment.
  • Tillie’s: This restaurant is located within the upscale resort Gurney’s. I can’t speak to the food on a regular day since we happen to come during Mother’s Day brunch. The food was pricey but OH SO GOOD. I think at one point I asked the baby if she can move over a bit in my tummy so I can have more crab legs lol.
  • The Lobster Roll: We stopped by here on our drive in. A great no frills place that has all the seafood staples. Funnily enough we did not have a lobster roll. Hubs had fish and chips and I had soft shell crab sandwich — both we’re delicious. Fans of the Showtime show The Affair might recognize this place as a location of a pivotal scene in the first episode.
  • Left Hand Coffee: great place for snacks and coffee pick me up and was conveniently located next door to my hotel


As far as where you want to stay, I think it highly depends on a number of factor. Montauk is littered with rental homes and hotels. I opted for hotel vs rental home since it was just going to be me and hubby. Also, even though I had a car, I wanted to stay at the city center so at I will have a good amount of food options that’s walking distance. Staying in the city center also means you’ll be able to forego the car rental cost and get to Montauk with the train and Hampton Jitney instead (assuming you’re coming from the city. With all that consideration, I ended up picking The Montauk Beach House. They we’re one block from the beach and not to mention I found an amazing deal since I was going at the start of the season. Bonus points: they have free continental breakfast, so that’s one cost I was able to shave off. Montauk food is not exactly cheap, so I’ll take any savings I can get.

Montauk Travel Guide
You can catch some great ocean views from the swings on the Montauk light house overflow lot

Montauk Travel Guide
Yes this pregnant lady climbed all the way up the lighthouse and was rewarded with some kickass views

Montauk Travel Guide
We opted to stay indoors at Duryea’s Lobster Deck but they do have space heaters and blankets so you can brave it out outdoors if you’d like

Montauk Travel Guide
Best part about Duryea’s Lobster Deck’s is the views and ambiance

Montauk Travel Guide
Duryea’s Lobster Deck’s food, while on the pricey side, was yum and super satisfying

Montauk Travel Guide
I absolutely adore the decor of Montauk Beach House, which made me felt like I walked into a Restoration Hardware store

Montauk Travel Guide
Their lobby is super cute as well and it’s where you’ll get to enjoy the continental breakfast

Montauk Travel Guide
Never met a free breakfast I didn’t like

Montauk Travel Guide
They also have free bike for guest use (I was too preggo to take advantage of this

Montauk Travel Guide
Technically I did get to enjoy the pool for a glorious half-day

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  • Samantha Mariko May 23, 2018 at 5:46 am

    Montauk looks so beautiful! I’d love to make a mini getaway out here someday :) You look so cute in your baby bump <3
    xo Samantha

  • Kileen May 24, 2018 at 2:29 am

    This looks beautiful and sounds so amazing! Need to bookmark this for future reference!

    cute & little

  • Kenzi || Life of a Sister May 24, 2018 at 8:11 am

    Montauk has wonderful views, doesn’t it? I love all of the eateries you picked! The bikes look so cute, and you look great in that swimsuit by the pool!

  • Annette Dattilo May 24, 2018 at 8:40 am

    Sounds like an amazing stay. I love the photo with the lighthouse in the back. So cool!

  • Taylor Mobley May 24, 2018 at 10:03 am

    What a fun place to visit!!!

  • Julia Comil May 24, 2018 at 1:48 pm

    Love these recommandations!! It sounds so fun for a weekend!!

  • Deborah May 24, 2018 at 2:50 pm

    I’m not going to lie, I’ve always wanted to go to Montauk because I watched “Eternal Sunshine of a Spotless Mind” when I was younger haha. What a fun place to visit!

  • Tara Fuller May 25, 2018 at 1:40 pm

    this sounds so relaxing- i love the scenery so much! definitely adding to my travel list!

  • Steph June 5, 2018 at 8:12 pm

    Looks so fun!! Thanks for the recommendations!

    xo, Steph |

  • Whitney June 5, 2018 at 8:31 pm

    I have always wanted to visit Montauk!

  • Denise Kokinis June 6, 2018 at 5:18 pm

    I have seriously always wanted to go, but have never been! You are making me think about booking a trip here! Love all these tips!

    Denise | Fashion Love Letters