6 ideas for Fall Weekend trips from NYC – and yes, some outfit inspo, too!
Tips: Weekend Etiquette
Here are some hard and fast rules for being a weekend houseguest: yes, you should look your best when visiting the future in-laws. Or staying at any rich friend’s beachfront villa, for that matter. Or on any Weekend trip! It’s called ‘manners’, my mom says. Don’t – DO NOT! – bring your old flip flops. (You know, the ones that make your feet smell like pickles. You thought your friends were crying in that movie? They were not. It was your feet making their eyes water.) Do show up with a thoughtful hostess gift: a chocolate babka from Zabar’s or a scented candle from Anthropologie. Also advised, bring a secret personal snack bag in case you aren’t allowed in the kitchen – I’ve known some hostesses to be super weird about the kitchen! And a robe for the inevitable middle of the night down the hall bathroom visit. And a bra. As the song goes, there’s a time for free-boobing, and there’s a time for not-free-boobing. This is not the time.
1. Sag Harbor
I’ve written about Sag Harbor in a previous post, and I still enthusiastically recommend it for a relaxing get-away weekend – and not just for honeymooners! It’s easy to get to, has pristine beaches, cool restaurants, and shopping – what more could a girl ask for? I am lucky to get to go out there often because my BF’s auntie owns a house which she generously invites us to spend time at.
The Hamptons have a certain blue blood reputation; but, IMO, one of the biggest benefits of going out East is that you can curate any type of experience you want. If you’re longing for the lazy days of summer, you can spend your weekend lounging at Havens beach. If you’re searching for family-friendly activities, you can go mini-golfing in Montauk. If you’re looking to bop to Beyoncé’s new single, you can explore the club scene (Gurney’s, Southhampton Social Club, Talkhouse, to name a few).
2. Long Island Vineyard Wine Tastings
Let’s be real – call it what you please but this so-called ‘wine tasting’ business is just Day Drinking at a nice place with amazing views! How great is that? And you are not required to swish sips of wine around in your mouth and expectorate into a bucket, like in the movies, thank goodness. No, they serve it to you in a regular glass, or you can order a ‘flight’ which means several smaller glasses of different types of wines. The pours are generous, and you’ll find that it’s quite a lot of wine to imbibe, especially when you are vineyard hopping, so be sure to partake of a charcuterie board and tapas selection. If you’re feeling sophisticated, you can sniff each glass, make a pronouncement to your friends – and write it down on the tasting notepad provided by the vineyard: “I detect hints of mushroom, pepper, and Granny’s purse”. Got a wine buzz? Yes, you do! Time to book the Uber driver.
The North Fork of Long Island has over 40 vineyards – something for every palate. Hop on the LIRR or the Jitney and make your way East to spend your Saturday at any combination of wineries. My personal favorite is Croteaux Vineyards, which produces traditional and sparkling rosé wine made from estate grown merlot, sauvignon blanc, and cabernet franc grapes. The outdoor tasting garden will make you feel like you’ve been transported to a Provençal Garden. Très bien.
3. Cruises
Did you know that you can walk over to the piers on the Hudson River and jump on a last minute cruise? True, you have to book it first, but you can do that at the very last moment – even the day before! You can sail away to Bermuda or Canada for a few days. Some people turn their noses up at cruises but, honestly, it’s probably the only place you’re going to be treated like a Rock Star everywhere you go!
4. Best Beaches
I love summer and I love New York. That doesn’t mean I love summer in New York. Yes, there is a plethora of fun things to do outside, but have you ever gone from 85 degrees outside to 100 degrees on the subway platform to 60 degrees inside the train car to walking up three flights of stairs all while 300,000 other people are crowding around you? Nothing cries BEACH DAY like sweating bullets through a cotton dress on the 6 train while your iced coffee leaves wet puddles on your knee.
There are New York residents who will try to convince you that Brighton Beach, Rockaway Beach, or even Coney Island Beach (yikes) are suitable summer excursions from the city. To anyone who willingly goes into that water I say, prepare for your radioactive superpowers to come into full effect soon. As a born and raised New Yorker, I am a full believer that you have to travel further East for the best beach day: Jones Beach, Robert Moses Beach, or Fire Island.
Depending on where you live, Jones Beach can be just as convenient as the aforementioned Borough alternatives; just take the LIRR to Freeport stop and switch to the nonstop n88 bus to Jones Beach. Pack a picnic lunch, that full-priced bikini you bought for your friend’s ill-fated 2020 bachelorette party, and plenty of SPF (reapply, people!) – and a beach umbrella is essential! A little bit further out is Robert Moses Beach – which technically is the Western part of Fire Island and the only section that can be accessed by car. It is less crowded than Jones Beach and you can actually walk to Fire Island from there (I’d recommend parking at Field 5).
5. Sightseeing tours
Why not be a tourist in your own city for the weekend? To be honest, the Viator bus tours might be the best deal in town. $58 for an unlimited ‘hop-on, hop-off’ pass around NYC. Did I read that correctly? I’ve spent $35 on an Uber going downtown from my place!
6. Day trips to Hudson River towns
Along the MetroNorth line lies several small towns comprising New York’s Hudson Valley. Just a couple hours outside of the bustling metropolis, you can experience Gilmore Girls-worthy small town laidback good vibes. I have been dreaming of blue skies and uninterrupted pastures ever since I started binge watching Little House on the Prairie last year. If you’ve recently purchased a Hillhouse Nap dress and a street fair sun hat, then you have your uniform ready for a day in the country. From Tarrytown to Cold Spring to Beacon to Hudson, each town is quaint and charming in its own right. At almost any stop along the way you will find sweet coffee shops, farm-to-table restaurants, and antique shops.
Depending on your budget, you might be interested in making a reservation at the two Michelin stars rated Blue Hill at Stone Barns in Tarrytown for a superior gastronomical experience. All the ingredients at the restaurant are sourced locally and there is no set menu; prepare to feast on the freshest offerings from the field and market. Beacon is home to excellent museums if that is your scene: Dia Beacon and Storm King are worth the trip (confession, Storm King isn’t technically in Beacon but is a short drive away!).
Hudson has recently undergone a Renaissance and is now the Hip capital of the Hudson Valley. Warren Street, the main drag, offers several shopping opportunities, none cooler than The Quiet Botanist, an apothecary-style store hidden in plain sight offering a range of unique goods that you won’t find anywhere else (dried flowers, tinctures, gardening supplies, and more).
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