Ah, it’s Autumn in New York, and really, there’s no better place to be. During these cozy few months, NYC fully comes to life. I mean, for goodness’ sake, this city is the backdrop for classic ’90s fall rom-coms (Hello, When Harry Met Sally, Autumn in New York, and You’ve Got Mail).
A weekend in New York is one of my all-time favorite fall getaways. There’s the foliage that covers the city in orange hues, all the fall fashion on full display, and the weather that hits near glorious temperatures. This Girl’s Guide to an NYC Weekend (Fall Edition) lays out the perfect itinerary for a fabulous couple of days in the city. This guide spotlights all the restaurants, bars, shops, neighborhoods, and activities that’ll make this an unforgettable trip for the girls.
Day 1: Downtown Girls
Morning: Start your day with brunch at Bubby’s in Tribeca. Bubby’s is known for its homestyle comfort food that tastes like if Thanksgiving, a fall candle, and heaven itself wrapped you up in a warm hug. Please don’t leave without trying their buttermilk biscuits (you’ll thank me later).
After you’re well and truly stuffed, spend a little time exploring the neighborhood. Walk around Tribeca and hit up some specialty stores like Philip Williams Posters and The Mysterious Bookshop. By this time, you might be ready for a little caffeine pick-me-up, and I definitely recommend Laughing Man Cafe to do the job.
Afternoon: Now, it’s time to walk on over to the West Village, so make sure you’re wearing your comfiest walking boots (or sneakers, ballet flats, heels— it’s okay, we embrace all footwear here).
Manhattan’s West Village is just downright dreamy. It’s a place where you walk around and internally sigh, while daydreaming about the gorgeous brownstone you own in your imagination. One of my favorite things to do in the West Village is to stroll aimlessly. In the fall, the brownstones are decked out in festive decor, and pumpkins take up prime real estate on the stoops. My two favorite streets for WV daydreaming are Bleecker Street and Perry Street.
Evening: Now, if you’re anything like me (and you might be considering you’ve come this far), late afternoon into the early evening means it’s time to start considering beverages— the adult kind. There’s no better place to quench that special thirst than Dante’s in the West Village. No, seriously, don’t just take my word for it, Dante’s was voted as the best bar in the world by the World’s 50 Best in 2019. Dante’s daily Martini Happy Hour is a special kind of paradise where the martinis come with ice chips (crucial) and olive sidecars (cute), all for the bargain price of $10.
Now, for dinner, you’re spoilt for choice, as the West Village is overflowing with some of the city’s best restaurants. There are old neighborhood institutions, new hot spots, and hidden gems in every corner. For a cozy fall dinner that is quintessentially New York, I recommend Fairfax, Cafe Cluny, The Waverly Inn, and Via Carota. If you’re in the mood for a sexy nightcap, stop by Pearl Box after dinner.
Day 2: Upper East Siders
Today’s mission is to tackle New York City classics in one of the city’s most iconic neighborhoods: The Upper East Side.
Morning: Start your day at La Bomboniera for hot chocolate, coffee, and pastries. Their Upper East Side location is intimate and warm, with fall decor scattered about the entire cafe. It’s the perfect place to get into the spirit of fall.
Like yesterday, there are even more festively decorated brownstones to swoon over on the Upper East Side. Their uptown counterparts are just as dreamy and remind you why there really is no place like New York in the fall. You’ll see plenty of them on your walk over to Central Park.
Afternoon: Now, no trip to NYC is complete without Central Park. It’s just a fact of life. Central Park in the fall is impossible to describe accurately, but alas, I will do my best. Simply put, the park is stunning this time of year, as trees of bright orange and red leaves complement the city’s skyline. The air is crisp in a way that only exists for a few short weeks, and it’s bustling with patrons just as in awe of all the colors and good energy in the park. This is the perfect place for a fall photoshoot, so whip out that camera and capture the moment, would you?!
After your glorious dander through the park, it’s time to head inside for a little respite from the cool weather. The Upper East Side is home to some of the best museums in New York. I personally recommend visiting the newly renovated Frick Collection, which is spectacular. Both the interiors and art within it are so impressive. Other museum options include The Metropolitan Museum of Art and The Guggenheim.
Evening: By this time, you might be ready for a cocktail. And, after all, it’s the Upper East Side, so there’s no better place to sit for a bevvy than at a hotel bar. One of my favorites is the Jacques Bar inside the Lowell Hotel. The drinks are made to perfection (I really, truly mean it), and it’s one of the chicest spots to sit for a pre-dinner drink.
For me, choosing a dinner spot on the Upper East Side is easy— it’s J.G. Melon. This little neighborhood gem is a cash-only pub that’ll serve you one of the best burgers and fries in the city. Despite its laid-back vibe, you’ll probably be waiting over an hour for a table because, yes, it really is that good.
Day 3: Quite a Lovely Final Morning
Morning: Noticeably absent from this itinerary are bagels. No worries, the time has finally come on your final morning in NYC. And really, you can’t go wrong with most local bagel spots in the city. Of course, there are the heavy hitters like Tompkins Square Bagels, Ess-a-Bagel, and PopUp Bagels, but I think visiting any bagel shop closest to wherever you’re staying will do the job just fine.
After breakfast, head downtown to the Brooklyn Bridge. Walking the Brooklyn Bridge towards Dumbo is one of the loveliest and quintessentially New York things you can do to round out your trip. I love this walk: I love the sheer busyness of it, the length of the walk, and the feeling of reaching the next borough on foot. Your walk across the bridge leaves you in Dumbo, which is one of NYC’s most picturesque neighborhoods.
Dumbo has a completely different energy from the high-energy and jam-packed downtown Manhattan, and I think it’s the perfect place to enjoy a relaxed final morning. While here, wander Washington Street for cafes, shops, and one of the most famous views of the Manhattan skyline. Then, make your way towards Brooklyn Bridge Park for more sweeping views and Jane’s Carousel. If you’re hungry for a bite before heading to the airport, stop by the Time Out Market for what is essentially a foodie’s paradise. Time Out Market has tons of food vendors giving you a taste of New York’s best bites.
