LongIsland.com’s 2014 October Family Fun Guide: Celebrate the Beginning of Fall With Festivals, Fairs, Concerts, and Other October Fun


October brings with it lots of festive fun! Check out this month’s fairs & festivals, Oktoberfest events, live musical performances, and other October fun you won’t want to miss.

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October is one of the most festive months of the year. The weather has turned cool and crisp and the breathtakingly beautiful Fall foliage is in full bloom. The kids are immersed in back-to-school and parents are back to work or enjoying the house to themselves while the kids are off getting their education. Smells of pumpkin spice, cinnamon, and baked apple pies surround the senses and fresh produce is ripe and ready for the picking at local farms and markets. Halloween brings with it frightful fun and haunted happenings from safe trick or treating events to haunted hayrides, spooky trails to costume parties, there is never a dull moment. In addition to all of this, and more, October brings with it lots of Fall fun for everyone to enjoy.

October is full of things to do for both kids and adults. Kids get to get all dressed up in creative costumes and travel from house to house asking for free candy and treats from the neighbors. The whole family can get together to carve up pumpkins, go apple picking or attempt to find their way through a complicated corn maze. Then adults can celebrate and enjoy a traditional brew or two during Oktoberfest.

With so much going on this month, LongIsland.com’s 2014 October Guide is here just in time to point out all of the best Fall fun and festivities that the Island has to offer. Be sure to leave some space open in your busy schedule and make the most out of Autumn this year with these various events, activities, and happenings going on around Long Island.

Festivals & Fairs
The month of October is full of fun for the whole family fairs and festivals! From pumpkin picking and scarecrow making to wagon rides and corn mazes, these events have it all! And don’t forget about all of the delicious foods!

Long Island Fall Festival FREE
Heckscher Park, 2 Prime Avenue, Huntington, NY 11743
Friday, October 10th - Monday, October 13th, 10/10 3 PM - 10 PM, 10/11 & 10/12 11 AM - 10 PM, 10/13 11 AM - 5 PM

Enjoy a fun filled weekend of food, contests, vendors, music, shows, and a carnival. Free parking available at the Huntington Train Station - $1 round-trip shuttle.

Apple Festival FREE
Islip Grange Park, 10 Broadway Ave., Sayville, NY 11782
Saturday, October 4th, 10 AM - 4:30 PM

Sponsored by the Town of Islip, this apple festival will feature an apple-themed cooking contest, pony rides, a carnival, a craft fair and more. Rain date is Sunday, October 5th.

Baldwin Fall Festival FREE
Baldwin LIRR Station, Sunrise Highway & Grand Avenue, Baldwin, NY 11510
Saturday, October 4th & Sunday, October 5th, 10 AM

Make your way out to Baldwin this weekend to see all of the arts & crafts, antiques, and delicious food for sale.

Amityville Apple Fest FREE
Park Avenue Gazebo, Amityville, NY 11701
Saturday, October 4th, 10 AM - 4 PM

Admission is free to this apple festival featuring live entertainment, paint a pumpkin patch, face painting, a craft fair, pony rides, and entertainment specifically for kids. Apples will also be available for sale by the bag along with yummy apple pies and donuts.

San Gennaro Feast of the Hamptons FREE
Good Ground Road (LIRR station), Hampton Bays, NY 11946
Saturday, October 4th - Sunday, October 5th, 10 AM

Come to the San Gennaro Feast to taste all types of food and wine, ride the carnival rides, visit the artisan vendor booths, and see a fireworks show on Saturday. Proceeds from the feast support the local school with scholarships, local charities namely Maureen's Haven and Coalition for Women's Cancers of Southampton Hospital.

Montauk Fall Festival FREE
Montauk Chamber of Commerce, 742 Montauk Highway, Montauk, NY 11954
Saturday, October 11th - Sunday, October 12th, 11 AM - 5 PM

Saturday’s festivities will feature a clam chowder tasting contest, farmers market, pony rides, pumpkin decorating, beer & wine, a children’s art contest, and fireworks. Sunday will include an Oktoberfest, crab races, and lots of tasty foods.

Collectibles Show FREE
VFW Post 4927, 31 Horseblock Road, Centereach, NY 11720
Sunday, October 5th, 10 AM - 3 PM

All you collectors out there won’t want to miss this show featuring sports cards, crafts, souvenirs, collectibles, DVDs, coins, toys, records, die-cast, comics, sports memorabilia, posters, autographs, pictures, Star Wars, and more.

Halloween Fun Festival FREE
Madison Theatre at Molloy College, 1000 Hempstead Avenue, Rockville Centre, NY 11571
Saturday, October 25th, 11 AM - 2 PM

This family friendly festival will have pumpkin decorating, mask making, a costume contest, corn maze, haunted house, scarecrow garden, and a concert at 2 p.m.

5th Annual Harvest Fest FREE
Port Jefferson Village Center, Main Street, Port Jefferson, NY 11777
Sunday, October 26th, 12 PM - 5 PM

Visitors will enjoy haunted walking tours, scarecrow displays, a farmers market, face painting, wood carving demos, pumpkin decorating, and much, much more at the 5th Annual Harvest Festival downport.

Huntington Historical Society Apple Festival
Daniel W. Missam House Museum, 434 Park Avenue, Huntington, NY 11743
Sunday, October 19th, 12 PM - 4 PM
Donations accepted

This event, happening rain or shine, will feature local apples, baked goods, scarecrow making, a butter churning demonstration, old-fashioned games, traditional music, storytelling, hayrides, and tours of the 1795 Kissam house.

Riverhead Country Fair
Peconic Riverfront - Downtown Riverhead, Riverhead, NY 11901
Sunday, October 12th, 10 AM - 5 PM
Please call for cost information

In true country style the Riverhead Country Fair will have farm animals, tractor pulls, folk music, pony rides, agriculture, homemaking, and needlecraft competitions all along the scenic Peconic riverfront. This is a festival you won’t want to miss!

Edgar Allen Poe Festival
Downtown Riverhead/Main Street along Peconic River, Riverhead, NY 11901
Friday, October 31st - Sunday, November 2nd, 3 PM on 10/31 & 12 - 8 PM on 11/2 & 11/2
Fees for some activities and events

This festival celebrating Edgar Allen Poe will feature a monster mash music party, haunted boat ride, storytellers, Vincent Price/Edgar Allen Poe movies, and street performers depicting the man himself and some of his well-known characters. Trick or treat stations will also be open on Halloween from 3-6 p.m. followed by a Halloween parade at 7 p.m.

Rockville Centre Chamber’s Food & Wine Festival
Front Street/Agnes area in front of LIRR station, Downtown RVC, Rockville Centre, NY 11570
Saturday, October 11th, 1 PM - 6 PM
$40 - $50

Join in on the delicious fun and enjoy some beer, wine, and food from Rockville Centre’s top chefs and food artisans. Appetizers, drinks, and live music will all be there at the festival.

Rockville Centre’s Restaurant Week
Participating RVC restaurants, Rockville Centre, NY 11570
Sunday, October 12th - Sunday, October 19th
$15 - $35

For a great price enjoy a scrumptious three course meal at one of the 20 participating Rockville Centre restaurants during Rockville Centre’s Restaurant Week!

Pumpkin Fest
Suffolk County Farm & Education Center, 350 Yaphank Ave., Yaphank, NY 11980
Saturday, October 4th - Sunday, October 5th, 11 AM - 5 PM
$12 per person, children under age 3 are free

Bring the whole family and come on down to Pumpkin Fest! There will be tons of things going on, like, pumpkin decorating, pony rides, pumpkin picking, wagon rides, carnival games, a corn maze, craft vendors, live bands, and much more.

Friends of Caleb Smith Preserve Fall Festival
Caleb Smith State Park Preserve, Jericho Turnpike, Smithtown, NY 11787
Sunday, October 5th, 10 AM - 3 PM
$10 per carload

This festival will have many activities geared to the natural features of the park, including catch-and-release fishing for children, nature walks led by popular naturalists, entertainment and face-painting. Fishing will be offered to children under age 13, worms and tackle will be provided. There will also be door prizes and a 50:50 raffle.

Christopher Morley Park Fall Carnival
Christopher Morley Park, 500 Searingtown Road, Roslyn-North Hills, NY 11576
Friday, October 3rd 6 PM - 10 PM & Saturday, October 4th 1 PM - 10 PM & Sunday, October 5th 1 PM - 6 PM
Admission is Free, $30 POP rides

Don’t miss out on this early Fall full-weekend carnival bonanza! The carnival will feature rides, games and food.

Fish Hatchery Fall Fair
Cold Spring Harbor Fish Hatchery and Aquarium, 1660 Route 25A, Cold Spring Harbor, NY 11724
Saturday, October 4th, 10 AM - 4:30 PM
$6 general admission, $4 ages 3-12 & ages 65+

This event will have exhibits by environmental groups and conservationists along with children’s games, nature-related crafts, and music. Rain date is Saturday, October 11th.

Fall Festival at Sagtikos Manor
Sagtikos Manor, Montauk Highway & Manor Lane, West Bay Shore, NY 11706
Sunday, October 5th, 11 AM - 4 PM

Bring the whole family out to experience life from the 1700’s! Watch the 3rd NY Revolutionary Regiment performing maneuvers, learn surgical procedures and remedies of the Colonial era, take a cemetery tour and listen to the history of the family members who reside there, and so much more.

Mill Neck Family’s Fall Harvest Festival
Mill Neck Manor School campus, 40 Frost Mill Road, Mill Neck, NY 11765
Saturday, October 11th & Sunday October 12th, 9 AM - 5 PM

Join in the fun at Mill Neck Family’s 53rd annual Fall Harvest Festival! There will be a wide variety of foods, including baked goods, specialty cheeses, meats, fudge, and roasted corn. There will also be craft vendors, children’s activities, and the latest in deaf technology and American Sign Language items.

Haunted Wail-ing Museum and Festival
The Whaling Museum and Education Center, 301 Main Street, Cold Spring Harbor, NY 11724
Sunday, October 26th, 12 PM - 4 PM
$10 adults, $5 children

This family event will feature crafts, a potion station, slime brewing, pumpkin picking, games, prizes, and more!

Live Music
Go out for the night to listen to one of your favorite musicians or discover new musical talent at a live performance on Long Island! Sing along to the lyrics and tap your toes in time with the tune while you have an awesome time out on the town.

Jimmy and The Parrots
The Emporium, 9 Railroad Avenue, Patchogue, NY 11772
Thursday, October 2nd, 9 PM
$7 - $10

You may not be able to make your way over to Margaritaville, but you can make your way over to the Emporium to enjoy a fantastic Jimmy Buffet tribute by Jimmy & The Parrots!

Limp Bizkit with Machine Gun Kelly
The Paramount, 370 New York Avenue, Huntington, NY 11743
Monday, October 6th, 8 PM
$34 - $60

Come out to Huntington to hear frontman Fred Durst and his fellow bandmates in Limp Bizkit play with Machine Gun Kelly.

The Wiggles: Ready, Steady, Wiggle! Tour
NYCB Theatre at Westbury, 960 Brush Hollow Road, Westbury, NY 11590
Sunday, October 5th, 1 & 4 PM
$22 - $70

The kids are going to have a blast singing and dancing along with the Wiggles as they make a stop in Westbury on their Ready, Steady, Wiggle! Tour.

The Kooks
The Paramount, 370 New York Avenue, Huntington, NY 11743
Thursday, October 9th, 8 PM
$25 - $35

This British pop group is heading to America to perform their Indie Rock hits that are sure to have fans fawning over their every word.

Blue Öyster Cult
The Space at Westbury, 250 Post Avenue, Westbury, NY 11590
Saturday, October 18th, 8 PM
$45 - $80

This American rock band, originally from Long Island, famous for such heavy hitting songs as “(Don’t Fear) The Reaper” and “Burnin’ for You,” will be rocking the stage at The Space in Westbury.

The Paramount, 370 New York Avenue, Huntington, NY 11743
Friday, October 31st, 8 PM
$30 - $60

Metal lovers won’t want to miss out on this Mastodon show with opening acts by Gojira and Kvelertak.

Rave to the Grave
Amityville Music Hall, 198 Broadway, Amityville, NY 11701
Friday, October 31st, 6 PM - 3 AM

Halloween night at Amityville Music Hall is all about electronic dance music and good vibes. The venue has a new dance floor, sound system, and lighting so be ready for a full night of house, electro, dance and dubstep music.

Oktoberfest Events
You don’t have to be in Germany to celebrate and enjoy Oktoberfest! Grab a nice cold brew at one of these Oktoberfest events around Long Island.

International Oktoberfest
Broadway Mall, 358 Broadway Mall, Hicksville, NY 11801
Saturday, October 25th & Sunday, October 26th, 11 AM - 6 PM
$10 per day

Enjoy a beer garden with craft beers from around the world and wine from local vineyards. Bring along a seat and some friends so everyone can have fun eating delicious international foods, listening to local musicians, and drinking great beer.

Riverhead Oktoberfest
Garden of Eve Farm, 4558 Sound Avenue, Riverhead, NY 11901
Saturday, October 25th & Sunday, October 26th, 10 AM - 5 PM

Riverhead Oktoberfest will feature crafts beers from all around Long Island, farm tours, pumpkin picking, vendors, and activities just for kids! Admission for those 21+ includes one free tasting from each brewery in attendance.

Oktoberfest 2014
Resurrection Lutheran Church, 420 Stewart Avenue, Garden City, NY 11530
Saturday, October 4th, 4 PM - 10 PM
$28 ($10 for ages 12 and under, children age 3 and under are free)

Get in the Oktoberfest spirit with German music, food and drinks. You’ll even get a commemorative mug! Net proceeds go to support the missions of Resurrection.

Westminster United Presbyterian Church, 109 Udall Road, West Islip, NY 11795
Saturday, October 4th, 10 AM - 4 PM
Call for price information

This Oktoberfest celebration will include a craft fair along with delicious German food and drink. The rain date is October 11th.

Other Outdoor October Fall Fun
It may be hard to believe but there are even more great festivities going on this October! Go check out a huge display of creative jack-o-lanterns, you may even see a familiar face or two! Or watch as a boat not fit for sailing is sacrificed and set-a-blaze in the spirit of tradition. With so much going on this October your weekends are sure to be jam packed until November!

Free Scarecrow Trail FREE
Caleb Smith State Park Preserve, Jericho Turnpike, Route. 25 West, Smithtown, NY 11787
Wednesday, October 1st - Friday, October 17th, 9 AM - 4 PM

Take a walk along the Third Annual Scarecrow Trail at Caleb State Park Preserve! Participants can pick up free scarecrow frames at the park, decorate them, and return them to be placed around the park trails. After October 17th you may pick up your decorated scarecrow and bring it home.

Halloween Boat Burning FREE
Long Island Maritime Museum, 86 West Avenue, West Sayville, NY 11796
Friday, October 24th

Come down to see a boat deemed too unsafe to sail set a-blaze in sacrifice while thousands watch from the shore enjoying an assortment festivities. Raffles, snack, hot apple cider, and musical entertainment are all to be found at the boat burning.

Fall Foliage Paddles
Quogue Wildlife Refuge, 3 Old Country Road, Quogue, NY 11959
Saturday, October 4th, 10:30 AM - 11 AM & 1 PM - 2:30 PM

Head out East to enjoy a 1 hour self-guided paddle tour on Old Ice Pond surrounded by beautiful fall foliage. Single kayaks are available for adults and children 12 and older. Children under 16 in kayaks must be accompanied by a supervising adult.

RISE of the Jack O’Lanterns
Old Westbury Gardens, 71 Old Westbury Road, Westbury, NY 11590
October 16, 17, 18, 19, 22, 23, 24, 25, 26, 29, 30, 31
$18 - $28, kids under 2 are free

Stare in awe at the 5,000 hand carved jack o’lanterns lighting up the night along the scenic trail at Old Westbury Gardens. You’ll definitely see some familiar faces in the pumpkins!

  • Fall Foliage Rides: Strap on your helmet and cycle your way through Autumn on one of these scenic bike paths.
  • Enjoy the East End: Discover all of the fabulous fun Fall things to do out in Eastern Long Island.
  • Fall Camping Sites: The Summer may be over but some camping grounds are still up and running for Fall visitors to enjoy.
  • Corn Mazes: Get lost in a corn maze this Fall...and find your way out too!
  • Furry Friends: Head out to the farms and petting zoos to find find furry friends to pet this Fall!

Don't forget to check out our 2014 Halloween Guide for the scoop on local haunted houses, tips on where to go trick-or-treating, and lots of scary-good fun!

Curious about other events and activities happening this October? Check out our Things To Do section and Events Calendar for even more fun Fall festivities!

Photo by Nancy Lowrie via Free Images