Updated 6/30/21
The DL: Montauk, also known as “the end of the world” or “the end”, thanks to being the second closest point to Ireland besides Cape Cod in the USA. Montauk is the furthest east end of Long Island and has the most laid back and chill vibe of them hamlets (Hamptons). Known for being a party scene and surfer town, we didn’t know what to expect on our first trip but you can find something for everyone to do for a weekend in Montauk. I get the hype it exceeded all expectations and should be on your list to visit especially if you are living in NYC.
For timing, our trip was in September the week after labor day, and the weather was perfect but got chilly at nights and once we were leaving started to drop into the 60s. We rented a car, I honestly think that’s the best way to see all the Hamptons and at the same time is the most cost-effective because ubers can rack up depending on where you stay or where you want to go. So yes, highly recommend a car for your weekend in Montauk especially in the offseason when traffic isn’t that bad. If you don’t want to rent a car, take the Long Island railroad or the Jitney (3 hours).
Since we had the benefit of driving through and stopping at other Hamptons on our way in or taking day trips, you can find that info here (soon) if looking to check out other Hamptons on this trip.
Day 1: A Weekend in Montauk
Check into hotel: Gurneys Montauk Resort and Seawater Spa
This is a splurge hotel but is worth every penny. You are right on the beach and everything feels so luxurious from the views, food, and service there is no other option like it.
Tip: Check out the prices on off days if you can take vacation during the week, or off months to make it more affordable.
We hung out at the beach and explored the hotel for the afternoon. The hotel does service on the beach if you want to order food or drinks.
Dinner and Drinks: Navy Beach and Crows Nest
Both are a must! The views are great at Navy beach and it feels like you are on an island. They have 2 other locations in the Caribbean and brought the vibe to Montauk. Make sure to get a reservation, they have seating indoors and many booths and picnic tables outside. The soy glazed halibut is delish.
After, we went to the Crows nest for dessert and drinks. During COVID the restaurant was all outdoors under string lights with fire pits all over the property. If you go down the hill by the water there are outdoor cabanas and seating you can eat at as well. You order online and can sit wherever you want, while the restaurant is closed. See below for how dreamy the lights are at this place:
Day 2: A Weekend in Montauk
Grab breakfast in Downtown Montauk:
- Jonis – Gluten free options, acai bowls, smoothies
- Goldbergs Bagels – there will be a line (pictured above), no gluten free
- Montauk Bake Shoppe – there will be a line here too
- Left-hand coffee – local coffee
- Johns pancakes – sit down option
Head to the state park and lighthouse:
Montauk Point State Park is home to the national landmark, the historic Montauk Point Lighthouse. Wear good shoes and plan to spend some time walking around the rocks and beach. This was one of my favorite parts of Montauk with beautiful views.
Tips: $8 to park and $10 a person for the lighthouse, walking around the beach is free
Lunch – Duryea’s Lobster deck and waterfront bar (get the full lobster grilled and one basket of fries it feeds two easily)
Explore Downtown Montauk:
- Shopping: A lot of the stores are pretty touristy in the downtown so I wouldn’t plan to spend to much time on shopping. if you are looking for higher-end stores or other local shopping head to the neighboring Hamptons, like east Hampton.
- Montauk brewing
- Ditch plain beach
- Star Island/ Lake Montauk
Dinner – Harvest Fort Pond (everything is served family-style, the oysters and steak are amazing. You also eat in the garden on the water in the middle of Montauk, so quaint)
- Surf lodge – evening bar scene
- Rushmeyers – go out
- Lairs Saloon – dive bar
- Lynns Hula Hut
Day 3: A Weekend in Montauk
Morning – Golf at the Montauk Downs State Park Golf course, Book a fishing charter, or hang out at the beach/pool!
Lunch – The Lunch aka Lobster Roll, famous for of course the lobster roll but they have a gluten free menu and serve montaukila margaritas.
Spend the rest of the day at the Beach
Dinner – Scarpetta at the Gurneys Hotel
One of my favorite pasta dishes by far, the short rib and bone marrow angolotti.
Spend the evening at the Fire pits at the hotel, they have their own menu and drink list, after 10 you must have reservations.
Other places to Eat on My List
- Gosmans
- The Surf Lodge
- Montauk Beach Club
- The Montauket
- Brunch at Arbor
- Muse
- Pizza Village
- Sel Rrose Montauk
- Inlet Seafood
- The Clam
- TTs Montauk – Mexican
Where to Go Out
- Surf Lodge – check the weekend line up
- Common Ground
- Ruschmeyers – get there early
- Montauk Brewing Co
- Montauket – chill, go at sunset
- Liars – get the mudslides
- Crows Nest – dreamy at night
- 668 Gig Shack – local fave
Montauk was a wonderful place, and we will be going back for sure. So many day trips if you feel like you have conquered this part of The Hamptons. A weekend in Montauk for the “full experience would be during peak Memorial Day – Labor Day, but we enjoyed the off peak just a week later because the weather was gorgeous, prices were cheaper and the restaurants were all still open!
Leave comments below of some of your favorite places in The Hamptons!
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