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The Best Things to do in the Seaport This Fall

Every October must-do at the iconic Seaport 🍂🥧🎃

by New York Bucket List


Fresh pies, an insta-worthy pumpkin arch, vintage finds and specialty pink, vanilla ice cream cones benefiting the American Cancer Society: it’s finally fall at the Seaport.

If this isn’t already your favorite time of year in NYC, allow us to convince you. The Seaport’s fall highlights include a host of tasty events and seasonal specials throughout the neighborhood. Here’s what’s on tap.

Hester Street Fair

Photo courtesy of Mike Szpot

Let’s ease into fall with some crisp local brews and warmed baked goods, and shop for cozy layers at the wildly creative Hester Street Fair. We love strolling the stalls and finding one-of-a-kind everything here—from vintage jeans to hand-poured beeswax candles—and that's just the tip of the small-biz/artisan-good iceberg. DJs Sammy and Wade will be spinning for shoppers, and selling a limited amount of their vinyl records, so you can take the vibes home with you.

Find your one-of-a-kind staple at its new location at the Seaport (recently moved from the Lower East Side).

When: Saturdays, October 30, November 6 and November 13, 11am–6pm
Where: Seaport Square, 89 South St., Bet. Piers 16 & 17

For more information on the Hester Street Fair, with their full roster here.

Pier 17 Pumpkin Arch

Photo Courtesy of CityHuntress

The uber instagramable Pumpkin Arch has returned to Pier 17! Up through early November, the massive arch frames the Brooklyn Bridge and makes for the most amazing fall photo ops.

Where: Located on the Heineken Riverdeck at Pier 17, which meets the East River and Beekman and South St.

Seaport Halloween

Photo courtesy of the The Seaport

All Halloween weekend is filled with spooktacular programming at the Seaport! The lineup includes:

Saturday, October 30, is the Halloween Hester Street Fair from 11 AM— 6 PM. Enjoy festive fall food, and an adult costume contest along with your shopping delight. You can also partake in the Seaport tradition of Trick or Treating for kids throughout the neighborhood. But don’t worry, there’s treats for the grownups, too: with a live DJ on the Fulton Street Stage and seasonal drink specials at Garden Bar. Other kids programming includes pumpkin painting hosted by the South Street Seaport Museum and crafts at McNally Jackson Books on Fulton Street. 

For Sunday, October 31 The Seaport will go full Halloween Block Party mode, with live music, face painting from 1:00–3:00pm, pumpkin painting with the South Street Seaport Museum and of course—more candy for the kiddos and seasonal drinks for the grown ups at the Garden Bar.

When: Saturday, October 30 & Sunday, October 31 

For more information on the Seaport Halloween

Experience The Times Of Bill Cunningham

Photo courtesy of Times of Bill

No one captured the city quite like Bill Cunningham, and a new exhibit at the Seaport is taking us through the legendary photographer’s work. Experience the Times of Bill Cunningham debuted at Live Rocket Studios during NY Fashion Week. Cunningham’s iconic Biria bike is part of this immersive experience, along with artifacts like his trademark blue French worker’s jacket. Unfolding over two floors, #TimesofBill features large-scale versions of Cunningham’s most iconic images, video interviews, and a city crosswalk simulation where visitors can strike a pose.

GA Tickets: $30
Where: Live Rocket Studios, 26 Fulton Street
When: September 12–October 30, Monday–Sunday: 10am–9pm (final entry at 8:30pm). Entry every 30 minutes. 150 max capacity per entry time.

For more information on The Times of Bill Cunningham

Fall Food & Drinks

Photo courtesy of The Funny Face Bakery

Autumn is a time to celebrate the harvest, and the Seaport does not skimp. Sip cozy cocktails at bars throughout the neighborhood, and make sure to try every fall flavor while you can! At Mister Dips, we recommend the Bacon Hatch Chili Burger and two special cones for October—the Think Pink (to support the American Cancer Society’s Making Strides Against Breast Cancer) and the Trixy Treat. At Funny Face Bakery, get a taste of fall with a pumpkin sugar n’ spice cookie. Or, pick up a freshly made pier from the local Fulton Stall Market, a local farmer’s market open daily on South Street. 

For more information on what to eat and drink at the Seaport


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