Return to Blog

Sep 10 Amazing Fall Festivals on Long Island’s East End

Autumn on Long Island is one of Hotel Indigo East End’s favorite times of the year. Pumpkin carving, apple picking, yummy food, Oktoberfest brews, and local festivals are just a few of our favorite traditions. To help you get in the fall weather spirit, check out 11 of our favorite East End celebrations.

Barnyard Adventure: Sept–Oct

Mattituck, NY at Harbes Family Farm

From September through October, the Harbes Family Farm offers a ton of family fun with its Barnyard Adventure. Kids can meet lots of friendly farm animals, explore the Gnome Hedge Maze, and play on the Jumbo Jumpers or trike track. For some other fun things to do, check out the Duck Race Games, Pig Races, and a Musical Chicken Show. Attractions are included in the price of admission and refreshments are available on site.

East End Maritime Festival: Sept 21–23

Greenport, NY

This annual tradition in the Village of Greenport brings tons of East End fun and fresh cuisine. The Maritime Festival kicks off with its Land and Sea Gala on Friday night followed by the annual parade on Saturday morning. Boat displays, kayak races, artisan vendors, music, dancing, food, and wine all add up to a fun fall weekend. If you’re bringing kids, don’t miss Sunday morning’s breakfast with mermaids and pirates.

Long Island Fresh Hop Festival: Sept 22

Riverhead, NY at LI Hops at Plant Connection

If you’re 21 or older, get a taste of fresh hop beers from local breweries at the Long Island Fresh Hop Festival on September 22 from 12:30 PM – 4 PM. Many of the beers offered are limited-edition. Plus, the festival offers catered food, live music, and other Oktoberfest-style ales to try.

Ode to Oktoberfest: Sept 29

Riverhead, NY at Hotel Indigo

One of Hotel Indigo’s favorite annual traditions is Ode to Oktoberfest. This year, we’re celebrating with Warsteiner Premium Beer, delicious Bavarian food, Smitty’s polka band, a keg-tapping ceremony, mug-holding contest, and a VR experience that’ll transport you to the Arnsberg Forest and the Hallertau hop region in Germany. Tickets for Ode to Oktoberfest can be purchased via ticketfly.com or at the door. Group tickets are also available.

San Gennaro Feast of the Hamptons: Sept 29–30

Hampton Bays, NY at the Long Island Railroad Station

The San Gennaro Feast of the Hamptons is more than just a celebration of delicious Italian cuisine. This festival, now in its 8th year, offers carnival rides, live entertainment, arts and crafts, a Fiat raffle giveaway, and a spectacular fireworks show. Don’t miss the Opening Ceremony Parade at 10:30 AM on Saturday, September 29.

Pumpkin Festival at Harbes Farm: Sept 29–30

Mattituck, NY at the Harbes Family Farm

The Harbes Family Farm celebrates the 2018 opening of its Barnyard Pumpkin Patch with The Annual Pumpkin Festival, which offers pick-your-own pumpkins, a donut-eating contest for the kids, singing hayrides, pumpkin-rolling competitions and much, much more. The farm is open from 10 AM to 6 PM both days.

Montauk Fall Family Festival & Clam Chowder Contest: Oct 6–7

Montauk, NY

Montauk’s Fall Family Festival celebrates its 37th year in 2018. At the festival, you can enjoy lots of fun activities including Saturday’s Clam Chowder Contest, a Chinese Auction, and Cash Catch Raffle on Sunday. There’s also live music, Oktoberfest-style food, Long Island beer and wine, a horse carousel, inflatables, and face painting.

Riverhead Country Fair: Oct 7

Riverhead, NY

43 years and going strong, the Riverhead Country Fair celebrates the area’s strong agriculture heritage with food and craft displays, contests, entertainment, carnival rides and pony rides.

Oktoberfest at Garden of Eve: October 27–28

Riverhead, NY at the Garden of Eve

Enjoy some relaxing family fun time in a pastoral setting at the Oktoberfest at Garden of Eve. Kids will enjoy farm activities like the lavender labyrinth, pedal cart track and friendly animals while you sip on craft beer from the brewery at Garden of Eve. The whole family can enjoy the great music, food, hayrides, pumpkins and mums that are sure to make up a perfect fall day.

Ragamuffin Parade: Oct 28

Sag Harbor, NY

Kids, adults, and furry friends are all welcome to dress up and join the annual costume parade down Sag Harbor’s Main Street. The Ragamuffin Parade starts at 1 PM on Nassau Street and ends at the Custom House Lawn where a bake sale and family games keep the fun going.


If you’re sore about summer winding down, be sure to add these events to your calendar and dive head first into fun, fall festivities.