Autumn is the best time of the year in New York for weather. With the crisp, dry air it is the ideal time to explore the outdoors, yet also get cozy indoors. In this guide, I’ll go over my favorite things to do in fall in the city. If you’re more of a visual person, watch my video below instead of reading this article. The purpose of this article is more to be used as a list so you can reference it while you’re out exploring the city!
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Boating in Central Park
Take a row boat out on Central Park’s lake. You can do this at Loeb Boathouse. It is $35 to rent but $20 of that is the deposit for the boat, so it is really only $15 (as long as you don’t damage the boat). Visit their site here
Insider tip: Go early to avoid crowds. If you are there during a busy time, head towards the bridge, go under it then head towards the other side of the lake. For some reason few people are on this side and it makes the experience more intimate.
Walk Through Central Park
Central Park is filled with hundreds of wooded trails that become magical looking with the golden autumn leaves. Explore it using Google Maps on your phone or head to the informations booth. There is a lot to see here and google maps has a lot of the sites embedded in the map.
Insider tip: Have a picnic at this hidden spot I found with an epic view.
Shakespeare’s Garden in Central Park
A rather less-frequented attraction of the park, the Shakespeare Garden is the perfect place for a relaxing afternoon in Central Park. The Garden covers four acres of plants that change according to season. Included among these are rosemary and pansies - alluded to by Ophelia in Hamlet; thistle - mentioned in the play Much Ado About Nothing; and even a white mulberry tree that is said to have grown from a graft of a tree planted by Shakespeare himself in 1602. More details on it here.
Swedish Cottage in Central Park
The Swedish Cottage, built in Sweden in 1875, was placed in Central Park in 1877 at the suggestion of Frederick Law Olmsted. Since its arrival in the US, the Cottage has served a variety of purposes, perhaps most importantly being used as the headquarters for the Civil Defense during World War II. It was also formerly a tool house, a library, and Central Park's entomological laboratory. More details on it here.
Date: October 29th from 4pm - 7pm
Bring the whole family and celebrate Halloween in Central Park. Enjoy pumpkin carving, Halloween crafts, spooky stories, a costume parade, and most of all the Conservancy’s signature Pumpkin Flotilla, which sets sail across the Harlem Meer at twilight! More details on it here.
Secrets of Central Park Tour
Together with your guide you'll experience some of the park's lesser-known treasures and explore the hard to find places that most people don't get to see, including the last remaining fortification of a site from the American Revolutionary War, a must-see 3500 year-old visitor from Egypt, and other attractions invisible to the average eye. More details here.
Visit Trinity Church and see Hamilton’s Grave
Trinity Church Wall Street is an active Episcopal Parish that has been an integral part of New York City’s history for more than 300 years. The oldest grave here is from 1681. Try to find it while you’re here!
One of the pieces this church is famous for is being home to Hamilton’s grave. He was secretary of state in 1789. However, today Hamilton is famous for another reason. Hamilton is a massive blockbuster hit that opened in New York two years ago. Since then it has broken many musical theatre records. If you’re a Broadway or history fan this could be a fun spot to visit. Visit their site here.
Insider tip: Act like a New Yorker and grab a coffee to go at Boundless Plains then sip on it as you stroll through the ancient cemetery.
One If By Land, Two If By Sea
One if by Land, Two if by Sea has been recognized for its classic menu, long history, and beautiful decor. It is often cited as the most romantic restaurant in New York City. The decor features candlelit tables, brick fireplaces, a baby grand piano and a private garden. More people are said to have announced their engagement here than any other restaurant in Manhattan.
The restaurant operates inside a historic, land-marked carriage house built in 1767 that belonged to Aaron Burr. Burr was the vice presidents of the US that killed Hamilton in a duel. It’s a fun connection if you just visited Trinity Church. This spot is known to be haunted by 20 ghosts - a perfect restaurant for the Halloween season. Visit their site here.
Insider tip: Get reservations far in advance. This place get’s booked quickly.
Take a Fall Foliage Cruise on a 1920’s Luxury Yacht
Admire the Palisades of the Hudson River through the skylights of our Classic Harbor Line’s heated and enclosed observatory, or while catching the breeze on her bow. Observe New York's most dramatic natural wonders and foliage as the seasons change. This is a spectacular season for cruising the Hudson River, north of NYC, will be a true delight for you and your guests. Visit their site here.
Insider tip: Book in advance.
GIVEAWAY: I have a giveaway going on right now to win two tickets to this. Enter here.
The Ghosts of Greenwich Village Scavenger Hunt
Armed with only a flashlight, you’ll visit ghost-plagued buildings and secret cemeteries while learning the stories of the restless souls you might disturb. Starring the spirits of Mark Twain, Aaron Burr, Edgar Allan Poe, Washington Irving, Thomas Paine, artist John LaFarge, the Shadow, Clement Clarke Moore, Mayor Jimmy Walker, Lee Chumley, Patrolman Schwartz, a few skeletons, and various other apparitions, sudden chills, rustlings, and knockings. See my experience doing this tour here.
Murder at the Met Scavenger Hunt
If the “Ghosts of Greenwich Village” hunt was too easy for you then try Watson Adventures most difficult tour, the Murder at the Met. Fans of murder mysteries and The Da Vinci Code will enjoy this scavenger hunt throughout the Metropolitan Museum of Art. A murdered curator has left behind a cryptic trail of clues connected with secrets in works of art. As your team gathers answers about the art, you begin to piece together a sordid tale about greed, lust, pride, revenge, and treachery, all revolving around the museum’s planned multi-million-dollar purchase of a rare painting by Leonardo da Vinci. See my experience doing this here.
Met Rooftop Bar
For some of the best views of Central Park head to their Cantor Rooftop Garden Bar. Here you can enjoy cocktails and light fare in an open-air setting with views of Central Park and the Manhattan skyline. Open through the end of October only (weather permitting). More details here.
Macy’s Thanksgiving Day Parade
Though this is more of a touristy thing to do I am including it because Thanksgiving is a holiday that mainly celebrated in the US. If you’re an international traveler, it could be interesting to see such an iconic USA parade while you’re in New York. Expect giant balloon, massive crowds, and wonderful performances. To see the performances get to Herald Square area very early. I found this article very helpful if you are planning on going to this.
Nov 22, 2018
Nov 28, 2019
Nov 26, 2020
Have a proper Thanksgiving Meal
If you want to experience a real thanksgiving meal I recommend booking a reservation on Thanksgiving at Joseph Leonard or Prime Meats (now called Frankies Spuntino Group) as soon as possible. Expect turkey, mashed potatoes, gravy, and all the good stuff.
Insider tip: If those spots are full check out this article for other suggestions.
Inferno Party at the McKittrick Hotel
I’ve talked about it in past videos and I’m mentioning it again! The McKittrick Hotel throws the most epic parties. There are a lot of Halloween events in the city but, in my opinion, they throw the best one. Don’t miss their Halloween party called “Inferno” coming up this October 26, 27, and 31st. Buy tickets here.
Bike Along the Hudson River Greenway
The autumn brings the most perfect weather to New York. I recommend renting a bike through Citi Bike then biking along the 11 mile stretch up to Fort Tryon Park along the Hudson River Greenway. Along the way you can stop at Boat Basin Cafe. It is a waterfront bar that serves beer, cocktails, wine and food. There are also tons of interesting other sites along the Hudson River Greenway while you make you’re way up.
Inside of Fort Tryon Park you’ll find The Cloisters. This fortress has a massive collection of medieval artwork. While you’re there make sure to take a break from the museum in their open air courtyard cafe. Please note thatThe Cloisters are part of The Met museum and is included in the ticket price to the main museum.
Insider tip: If you want to do this plan a whole day around it so you can see everything.
Great Jack O’Lantern Blaze
Meander through an 18th-century landscape and discover a breathtaking display of more than 7,000 illuminated jack o’ lanterns—all designed and hand-carved on site by our team of artisans! Witness a windmill go round and round (with pumpkins all around). Visit our brand new medieval castle and listen for the who-whooo… a flock of jack o’lantern owls is standing guard! Star cross your selfie game with Instagrammable-scale signs of the zodiac. Visit their site here.
2018 Dates: October 4-31, November 1-4, 7-11, 15-17, 23-24
Insider tip: Buy tickets in advance because this sells out quickly.