MDW in Montauk
This past weekend, I went to Montauk with five of my best friends and was lucky enough to have two of them locking down the reservations and itinerary for everyone. We went to Surf Lodge for brunch the first day, which is definitely a good choice if you want to be able to get in early instead of waiting in line later on in the day. The service was rather slow (it was the first weekend of the summer), but there were a wide variety of brunch options and everyone generally enjoyed what they ordered (burger was very good, lobster roll was okay). Cocktails range from $16-18 and the Montauk Summer Ale, Corona, and Red Stripe are the only beers they have (none on tap). They do have some fun punch bowls though!
We went to Swallow East for dinner that night, which I would highly recommend (s/o to Josh for hooking us up with the chilled Tallulahs). The menu is small-plate focused, so it's meant to be shared between everyone which worked for the six of us. Menu favorites were the scallops, calamari (sweet & spicy Thai glaze), asparagus fries, and seared ahi tuna. They also have live music six days a week!
Sunday morning was cold and rainy, but we went to brunch at TIllie's at Gurney's. Everyone really liked what they got - I loved the lobster roll, calamari, and sweet potato fries. We got pancakes for the table, which weren't the BEST EVER but a solid option if you're craving a sweet brunch dish to split.
Unfortunately it was raining the whole day, so we went to check out Montauk Brewing Co. It's a really small space with only three tables or so, but they had a tent set up outside for people to stand under. It is definitely worth checking out and obviously is more fun if you can stand outside when the weather is nicer.