As you probably know, I love planning fun weekends outside the city. Over the past 10 years of living here we have had the chance to experience and try a few amazing places not too far away. Each place is either a quick (ish) train ride or drive (bus included) away. Places that you can escape to, relax and unwind. I tend to get a bunch of NYC based questions and those blog posts tend to be a hit, so I thought this would be helpful for all my fellow New Yorkers as well as anyone that may be visiting and looking for a weekend trip!
– GREENPORT, NY –
Greenport: This may be one of the cutest towns we have ever been to! It is about a 2 and 1/2 hour trip out of NYC and you can get there by all three modes of transportation: train, car or bus. Matt and I went to Greenport last September and I wrote an entire travel guide here. From the waterfront, vineyards and incredible food, you’ll definitely want to make a weekend out of this place. We are dying to get back and hope to do so later this summer or early fall. We have heard that harvest season at the vineyards is in October and it’s a great time to visit. There is so much to see, do and explore and if you can, try and get around by bike, it is a fun mode of transportation!
– SHELTER ISLAND, NY –
Shelter Island: I actually touched on this place in my Greenport post because we took a 5 minute ferry ride (with our bikes) from Greenport over to Shelter Island to explore. Unfortunately we were a but too late in the season and almost everything was closed, so I suggest if you are wanted to head there, do so before September. But from everything I have heard this is a really fun summer destination, with beautiful beaches, quaint bed and breakfasts, and very low key mentality.
– MONTAUK, NY –
Montauk: Another fun escape from the city is Montauk, which is also one of the furthest points out on Long Island. While the train is anywhere from 3-3.5 hours, once you arrive it is worth it! I would say Montauk is a bit on the younger side, consisting of a lot of post-college students that rent shares together. However, we did go for my 30th birthday last year with a group of friends and had a blast! You can find that blog post here, which goes into detail on where we ate and what we did.
– EAST HAMPTON –
East Hampton: Also out on Long Island, but a little closer than Montauk is East Hampton. This is your quintessential escape from NYC where each home is perfectly landscaped, hydrangeas in full bloom, the town is quaint and beaches pristine. It actually reminds me a bit like Nantucket is you have ever been!
We recently went for a trip here and were so fortunate to stay at our friend’s insanely beautiful home. We spent the weekend pool and beach side, and checking out the cute town of East Hampton. On Saturday, we had reservations at Wolfer Kitchen in Amagansett and it was incredible!! I would highly recommend the skinny spicy jalopeno margarita, the octopus and oysters. This location was perfect because we were heading to The Stephen Talkhouse afterwards to listen to live music, which was located just across the street.
– FIRE ISLAND, NY –
Fire Island: This will always be one of my absolute favorite escapes from the craziness of the city! We have been going here with Matt’s family for the past few years and this summer was the first year we weren’t able to make it happen with everyones schedules, but we all agreed we need to figure it out for next year! Right of out college Matt and I would come here with friends, but we would stay in Ocean Beach, which is much more of a “party scene” (full blog post here). With Matt’s family we discovered Kismet, which is WAY more my scene at the age of 31 haha (full blog post here). It is super low key (literally Hadley isn’t on a leash once), and Matt’s parents rent a house that is practically right on the beach. I always joke that the only time I put shoes on while I am there is when we head to one of the two restaurants in town.
If you aren’t familiar with Fire Island, it is a bit of a process to get to from NYC, but all the trains, planes and buses (jk….kind of) are totally worth it! You take the LIRR from NYC to Bay Shore (about an hour ride) and from there you are picked up by a shuttle/taxi service to take you on the 5 minute drive over to the ferry, which then you take over to Fire Island (about 30 minutes depending where on the island you are being dropped off). You can purchase the train AND shuttle tickets in Penn Station, just an FYI. I talk about more of the details (how you need to pre-order food to get delivered to the island, etc.) in my blog post, so if you are interested in going, but haven’t been, make sure to give it a good read!
– QUONOCHONTAUG / WATCH HILL, RI –
(sorry for the iPhone photos, I can’t find my camera card with the pictures I took!)
Quonochontaug/Watch Hill: Honestly one of the most adorable places ever, nestled right along the water in Rhode Island. I discovered this place through my friend’s bachelorette and we had the BEST time! Don’t leave without starting your day with coffee from the cutest local shop, Dave’s Coffee, grabbing a meal from Matunuck Oyster Bar, a drink at the Ocean House while admiring Taylor Swift’s home on the cliff (but first walk around the town that is about a 5 minute walk away) and order take-out (lobster rolls and all the seafood) and have dinner on the beach! Dying to get back here and bring Matt and Hadley next time. The Amtrak is about a 3 hour ride.