September
Feast of San Gennaro
Feast of San Gennaro | Stuart Monk / Shutterstock.com

September

Tuesday
Sep 6
Columbus Circle
Watch multi-talented jazz singer Leslie Odom Jr. (aka the original Aaron Burr from Hamilton) perform hits from his recently released album for free at The Shops at Columbus Circle.
Friday - Sunday
Sep 9-11
Southampton
Blade/T-Mobile's Same-Day Slingshot experience will fly you out to Southhampton (and back!) for a day filled with lots of rosé and lots of beach time. The price is $295 each way, but it still beats the Jitney traffic. 
Saturday
Sep 10
Worth Square
Madison Square Eats is back in Worth Square with food from vendors like Melt Kraft, Hill Country BBQ, Red Hook Lobster Pound, Roberta's, and more.
Thursday - Saturday
Sep 15-17
East Village
The first-ever Astor Alive! Festival will honor Astor Place with things like free theater and dance performances, poetry readings, arts workshops, and more. Narcissa will also be giving out free ice cream from an ice cream cart from 1-5pm on Saturday. 
Thursday - Sunday
Sep 15-25
Little Italy
This 11-day Italian extravaganza pays tribute to the patron saint of Naples with live music, colorful parades, religious processions, and of course, tons and tons of food.
Friday
Sep 16
Metropolitan Pavilion
Sake lovers (or those who want to love it) can sip on over 400 different sakes and sample dishes from 16 NYC restaurants including Sushi Nakazawa, 15 East, and O Ya, with tickets starting at $95.
Saturday
Sep 17
E 7th St btw Cooper Square & 2nd Ave
Enjoy food & drinks from some of the East Village’s most popular dining institutions, including Luke’s Lobster, Butter Lane Cupcakes, and Porchetta. Tickets start at just $25, with proceeds going towards charitable endeavors within the neighborhood.
Saturday - Sunday
Sep 17-Oct 2
Celebrate Oktoberfest in NYC
Celebrate Oktoberfest in NYC
Multiple locations
Get into the German spirit at beer halls and bars across the city (that means lots of beer, brats, and pretzels).
Sunday
Sep 18
Randall’s Island
Enjoy a brisk 5K course that ends at an expansive beer festival (as all marathons should) with brews from some of the state’s best breweries (including Brooklyn Brewery, Sixpoint, Rockaway Brewing, Captain Lawrence, and Alphabet City Brewing), plus food and live music.
Sunday
Sep 18
East River State Park
Dine out at this culinary block party featuring over 50 North Brooklyn restaurants, bars, and breweries, and live music. Proceeds will go towards constructing the North Brooklyn Community Center housed in the former Engine 212 Firehouse, with tickets starting at just $35.
Thursday
Sep 22
Union Square Park
Chefs from the best restaurants in Union Square (Blue Smoke, Union Square Cafe, Gramercy Tavern, Hill Country Chicken) will offer tastings utilizing fresh produce straight from the Union Square Greenmarket.
Friday - Saturday
Sep 23-24
69th Regiment Armory
Sample over 250 wines and track your favorites on the event’s handy app.
Saturday - Sunday
Sep 24-25
The Old Pfizer Factory, Williamsburg Brooklyn
Go HAM, literally, at this indoor/outdoor gourmet festival featuring countless bacon dishes and local craft brews. General admission tickets start at $79.
Wednesday - Sunday
Sep 28-Oct 2
Metropolitan Pavilion
Browse a huge selection of paintings, sculptures, and photographs, with pieces priced from $100-$10,000.
Friday - Monday
Sep 30-5
163 Varick St
The famed haunted house is back with more blood, gore, and creeps than ever.
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October
Tompkins Square Halloween Dog Parade
Tompkins Square Halloween Dog Parade | Donald Bowers Photography / Shutterstock.com

October

Saturday - Sunday
Oct 1-2
Flushing Meadows Corona Park
Head to Queens to see See Kanye, the Weeknd, Chance the Rapper and more at the Meadows Music & Arts Fest.
Saturday - Sunday
Oct 1-30
Staten Island
Head to Staten Island for hayrides, face painting, farm animals, and pumpkin picking -- all without having to head to the country!
Wednesday
Oct 5
155 Sullivan St
Eat $1 pizza samples from the city’s best pizzerias, with 100% of proceeds going towards eliminating hunger in NYC.
Friday
Oct 7
NYU Skirball Center for the Performing Arts
Film Independent is bringing its Live Read series back to New York with a totally unrehearsed live reading of Good Will Hunting by a mystery "all-star cast" (it's directed by John Krasinski, who will release the cast names on his Twitter account prior to the event). Get tickets here.
Thursday - Monday
Oct 13-31
Randall’s Island
Spook yourself silly on this Halloween attraction that’s so terrifying, Mark Cuban from Shark Tank invested in it! Tickets start around $35.
Friday
Oct 14
Pier 92
This is a pricey one -- we’re talking $225/ticket! -- but with participating chefs like Rachael Ray, a celebrity judges table that includes Michael Strahan, great burgers, mac & cheese, live music, and tons of beer, burger fanatics should be happy to splurge on this NYCWFF event.
Friday - Saturday
Oct 14-15
The Bronx Zoo
Enjoy this adults-only (21 and over!) overnight sleepover with dinner, drinks, trivia, and seriously up-close encounters with your favorite zoo animals.
Sunday
Oct 16
Various locations
The NYC Wine & Food Festival runs Oct 13th-16th, with everything from cooking demonstrations, to wine tastings, to private dinners, and more, but don’t miss out on our own Coca-Cola Backyard BBQ, hosted by Bobby Flay and Michael Symon on the rooftop of Pier 29, with food from Hometown Bar-B-Que, Dinosaur Bar-B-Que, Fleishers Craft Butchery, Hill Country Barbecue Market, and more.
Sunday
Oct 16
Queens Botanical Garden
This family-friendly event features live music, bouncy houses, food, drinks, and an enormous pumpkin patch.
Saturday
Oct 22
Tompkins Square Park
Let your dog be the star at this annual Halloween event where the pooches ALWAYS upstage whatever you have planned for your costume.
Sunday
Oct 23
Williamsburg
Don't miss out on tickets ($10 for early-birds, $15 for GA) to the ultimate dessert-lover event in Williamsburg, which will feature tastings and workshops from 20 vendors from around the city, including Jae NYC Eats, Mochidoki, Wowfulls, and Mini Melanie (plus Intelligentsia Coffee).
Saturday
Oct 29
Capitale
Pretend you’re someone you’re not at this annual Halloween bash with costumes, masks, and fist-pumping DJ tunes -- tickets start at just $10.
Monday
Oct 31
West Village
For 43 years the Village Halloween Parade has been THE place to party, dance, and show off your costume.
November
NYC marathon
NYC Marathon | Eduard Moldoveanu / Shutterstock.com

November

Sunday - Monday
Nov 6-7
East Williamsburg
Featuring over 100 growers, RAW WINE celebrates natural, low-intervention organic and biodynamic wines and the health benefits that come with them. Tickets start at $50.
Saturday
Nov 19
Various locations
Known as “Cranksgiving,” this charitable event asks you to bring a bike, a bag, a lock, and about $20 to purchase food. Everything collected will benefit the Bowery Mission.
Thursday
Nov 24
Your couch and/or 6th Ave
Whether you watch it on the streets or from the comfort of your home (home, definitely watch from home), there’s no excuse not to catch this annual spectacular.
Tuesday - Saturday
Nov 29-Dec 24
Columbus Circle
Need a trinket for your grandma or a tzatchki for your great aunt? Get it out of the way early at the Columbus Circle Holiday Market (running ‘til Christmas Eve).
December
SantaCon
SantaCon | a katz / Shutterstock.com

December

Thursday - Saturday
Dec 1-31
New York Botanical Garden
Gaze at model trains zipping around miniature NYC landmarks at this charming, family-friendly show.
Saturday
Dec 10
Various locations
You have two options: either participate in NYC’s most simultaneously hated and beloved event, or stay indoors and do not leave for 24 hours.
Monday
Dec 19
Brooklyn Museum
Get into the holiday spirit with this annual tasting celebrating the best latkes NYC has to offer.