While many wealthy New Yorkers flock to the Hamptons for their weekends over the summer, this isn't exactly the most accessible and affordable NYC weekend destination. Sure, the Hamptons are beautiful, but you can find many of the same things (quaint little towns, nice beaches, good restaurants) in Long Island's less expensive, less touristed North Fork. As a bonus, they have a really great wine country out there as well. Over this past summer, I had the opportunity to spend a long weekend here as a quick break from NYC. While still not cheap, it's a much more affordable and less pretentious alternative to the Hamptons, where you can escape the city and go to the beach.
To get there, take the Long Island Railroad to Greenport. It takes about 3 hours one way from Penn Station, and you'll have to switch trains at some point. But it is a very cheap way to get out there! This is what I recommend if you are staying in Greenport. If you want to leave the town at all and visit the wineries, you'll probably want a car. You can rent one and drive out in about 1-2 hours, but it's a bit more expensive. I tried using Uber and the local taxi service to get between vineyards, but it was very slow and expensive so I honestly wouldn't recommend it.
Stay in a local Airbnb! There are so many lovely local bed & breakfasts and people who rent out rooms in their homes. Support the local economy instead of staying at the chains! We rented a room in someone's home, and she cooked us a great breakfast as well as gave us the best recommendations for where to go to the beach and where to eat. If you're going with a group of friends, pitch in to rent a house together on Airbnb. I definitely recommend staying in the actual town of Greenport, there's lots of great restaurants and shops. We also stayed one night on a vineyard in Cutchogue, which was really incredible but definitely more of a splurge.
Everything was very COVID safe too! While we went during the summer when cases were extremely low in New York, more than 99% of people there wore masks correctly indoors and outdoors (much better than in the city), and there was hand sanitizer and social distancing in every business. Most activities here can be done outside/socially distant anyway, so it's a great spot to put on your summer 2021 list.
Without talking too much more, here is a recap of how I spent my long-weekend spent on the North Fork. Again, I'd recommend renting a car if you'd like to see the vineyards, but otherwise I think my recommendations are pretty solid (lol).
10am: Take the LIRR from Penn Station to Cutchogue.
1pm: Explore the town by foot and check out some of the tasting rooms. Stop at the organic market downtown and grab some snacks. Call a cab over to Sannino Vineyard, where you'll stay the night.
3pm: After checking into Sannino's B&B, walk through the vineyard over to their tasting room and try their delicious wines.
7pm: Head to your dinner reservation in town at Touch of Venice for a nice Italian meal.
10am: Head into the town of Greenport to check into your Airbnb. Walk into the town and explore by foot.
12pm: Grab a healthy lunch at Ellen's on Front.
1pm: Walk around and check out some of the shops. Make sure to visit Kharmah for cute, summery, ethically-made clothes and Weathered Barn for cool gifts. Check out Burton's Books to find a good book that's on your list.
6pm: After walking around all afternoon, head back out to Noah's for a nice dinner with some great modern American cuisine. A lot of their ingredients are locally-sourced.
8pm: Hit the town at night and check out the bars on Front Street. Go inside and grab a drink in a to-go cup, then hangout outdoors. There's also a great bar on the beach, walk along the beach path and you'll find it.
10am: Sleep in and have breakfast at your Airbnb.
12pm: Grab some delicious tacos from Lucharitos in downtown Greenport, then head out to any of the local beaches you have access to for tanning and swimming. Spend the afternoon at the beach getting some sun!
6pm: Head to your dinner reservation at Olive Branch, a delicious Mediterranean restaurant on Front Street.
8pm: Walk along the port and check out all the interesting boats. Walk along the water, and grab another drink at that same beach bear.
11am: Head out to a hearty but healthy brunch at Bruce & Son in downtown Greenport.
2pm: Catch the LIRR from Greenport back to Penn Station in NYC so you're back in time to decompress from the weekend.
Those are my tips for having a great weekend on Long Island's North Fork. It really is the perfect relaxing weekend destination from NYC. There is a slow, refreshing pace of life, and the people are all kind and friendly. Also, there's great wine. Check it out!