If fall on Long Island had a personality, it would probably involve a street fair, a cider doughnut, live music, and someone carrying around a pumpkin they absolutely did not need.
And honestly? That sounds about right.
Fall festivals on Long Island are one of my favorite things about this time of year. Once the weather cools down, suddenly every weekend brings another reason to get outside — downtown streets filled with vendors, food trucks lined up around the block, local musicians playing, kids bouncing on something inflatable, and at least one booth selling something you didn’t know you needed until you saw it.
There are A LOT of events to choose from, so I pulled together some of the fall festivals and street fairs happening around Nassau County and Long Island in 2026 that are worth putting on your calendar.
Whether you’re looking for Nassau County fall festivals, classic street fairs on Long Island, or a bigger festival worth the drive, something is happening almost every weekend this fall.
And because dates change, weather happens, and Long Island apparently likes to schedule six festivals on the same weekend, I’ll keep this guide updated when I find something you need to know.
Best Fall Festivals on Long Island in 2026
Let’s start close to home.
Plenty of fall festivals and street fairs are happening throughout Nassau County this October, from giant events that can fill an entire afternoon to smaller community fairs that are perfect when you just want to get out, walk around, and eat something from a food truck.
Here are a few I’d put on the calendar.
Fall Festivals & Street Fairs in Nassau County
Franklin Square Street Fair | October 3
Where: Franklin Square
When: Saturday, October 3, 2026
Time: 10 AM–5 PM
Let’s start the month with an easy one.
The Franklin Square Street Fair brings vendors, food, and family fun together for a full Saturday out. Organizers say a typical fair can bring roughly 65–75 vendors in good weather. Nassau Arts & Crafts Fairs
Why I’d put it on the list: It’s exactly the kind of community event that feels like fall on Long Island — browse a little, eat something you probably weren’t planning to eat, and see what you find.
Franklin Square Street Fair details
Massapequa Park Village Street Fair | October 4
Where: Park Boulevard, Massapequa Park
When: Sunday, October 4, 2026
Time: 10:30 AM–4:30 PM
Admission: Free
Rain date: October 11
Now we’re talking BIG street fair.
The annual Massapequa Park Village Street Fair takes over Park Boulevard with more than 200 vendors, three live bands, food trucks, and a huge kids’ fun zone with inflatables, a mechanical bull, a rock wall, and the Pequa Choo-Choo Express. Long Island Fairs
Why I’d put it on the list: If your ideal street fair is less “I’ll stop by for 45 minutes” and more “well, I guess we’re spending the day here,” this is the one.
Rachel tip: Go earlier rather than later if crowds aren’t your thing. More than 200 vendors + food + kids’ attractions = this is not exactly a secret little neighborhood event. 😂
Massapequa Park Street Fair details
Bethpage Street Fair | October 4
Where: Bethpage
When: Sunday, October 4, 2026
Bethpage joins the October 4th party with its annual street fair, which is currently listed on the Nassau County Fairs 2026 calendar. Nassau Arts & Crafts Fairs
This makes October 4 a particularly good pick-your-town day in Nassau County.
Why I’d put it on the list: It’s a classic local street fair and an easy choice for anyone in central Nassau who doesn’t want to turn the day into an expedition.
Check Bethpage Street Fair updates
Long Beach Fall Festival | October 10–11
Where: Kennedy Plaza, Long Beach
When: Saturday & Sunday, October 10–11, 2026
Time: 10 AM–5 PM
Admission: Free; individual attractions are additional
The Long Beach Fall Festival is one of those events that checks almost every fall box without requiring a drive out east.
We’re talking a huge pumpkin patch, kids’ crafts, rides, vendors, food, live entertainment, and a costume parade on Saturday.
For 2026, the city is bringing back attractions including the Pumpkin Bounce House, carousel, and hay wagon ride. Adults aren’t forgotten either: there will be food vendors plus a beer, wine, and food experience for guests 21 and older. Long Beach, NY
Why I’d put it on the list: You get fall festival + downtown Long Beach + the ocean right there.
That’s a pretty good October combination.
And yes, I would absolutely turn this into lunch or dinner afterward.
Long Beach Fall Festival details
Eisenhower Park Craft & Gift Fair | October 10–11
Where: Eisenhower Park, Field 8, East Meadow
When: October 10–11, 2026
If your favorite part of a fall fair is wandering through vendor booths, put Eisenhower Park’s October Craft & Gift Fair on your list.
The two-day outdoor event at Field 8 is currently scheduled for October 10 and 11. Nassau Arts & Crafts Fairs
Good for: Shopping local, finding handmade gifts, and getting outside without needing an entire day’s itinerary.
Check Eisenhower Park fair details
Mineola Fall Festival | October 17–18
Where: Mineola Memorial Park, 195 Marcellus Road
When: Saturday & Sunday, October 17–18, 2026
Time: 12–6 PM
Rain dates: October 24–25
The Mineola Fall Festival at Memorial Park combines food, artisanal beer and wine, live music, a vendor market, kids’ activities, and a pumpkin patch. Mineola Fall Festival
Why I’d put it on the list: This feels less like a traditional street fair and more like an actual autumn festival.
If you want food + music + pumpkins + shopping in one place, this one covers a lot.
Oyster Fest | October 17–18
Where: Theodore Roosevelt Memorial Park + Downtown Oyster Bay
When: Saturday & Sunday, October 17–18, 2026
If you’ve lived on Long Island for any length of time, you’ve probably heard of this one.
Oyster Fest is HUGE.
The 43rd annual Oyster Fest returns to Oyster Bay on October 17 and 18, taking over the waterfront and parts of the historic downtown. The festival includes food, arts and crafts, amusement rides, entertainment, and the famous oyster eating and shucking contests. Town officials say the event can attract up to 200,000 visitors. Town of Oyster Bay
So yes:
Plan accordingly.
Rachel tip: This is absolutely NOT the weekend I’d casually drive toward downtown Oyster Bay at lunchtime and hope the parking gods smile upon me.
Take a minute before you leave to check the festival’s current transportation recommendations.
Why it’s worth it: Oyster Bay is already one of my favorite North Shore places to spend a fall day. Add a huge waterfront festival, and you have a very Long Island October weekend.
Rock Hall Country Fair | October 17–18
Where: Rock Hall Museum, 199 Broadway, Lawrence
When: Saturday & Sunday, October 17–18, 2026
Time: 11 AM–5 PM
Admission: Free
Parking: Free
This one is a little different — and that’s precisely why I like including it.
The 40th Annual Rock Hall Country Fair mixes fall fun with history. For 2026, expect colonial historians, a harvest market, craft vendors, antique cars, farm animals, pony rides, children’s crafts, a pumpkin patch, and a make-your-own-scarecrow activity. Friends of Rock Hall
Why I’d put it on the list: If you’ve already done your share of food trucks and inflatable slides, this has a completely different feel.
Rock Hall Country Fair details
Nassau Boulevard Street Fair & Foodie Fest | October 18
Where: Nassau Boulevard overlooking Hall’s Pond, West Hempstead
When: Sunday, October 18, 2026
Time: 10 AM–4 PM
Admission: Free
Rain date: October 25
The Nassau Boulevard Street Fair & Foodie Fest has a particularly pretty setting alongside Hall’s Pond and includes dozens of artisans and vendors, food trucks, a kids’ fun zone, and live music. The October 18 date is a new date for 2026. Long Island Fairs
Why I’d put it on the list: This feels like a nice middle ground between a small neighborhood fair and one of the enormous destination festivals.
Nassau Boulevard Street Fair details
Merrick Fall Festival | October 23–25
Where: Merrick LIRR Station area, Sunrise Highway & Merrick Avenue
When: Friday–Sunday, October 23–25, 2026
Street fair: Saturday & Sunday, 10 AM–5 PM
Carnival: Friday evening through Sunday
Merrick closes out the big October street-fair calendar with a full Fall Festival weekend.
The carnival gets started Friday evening, with rides continuing Saturday and Sunday. The street fair portion runs Saturday and Sunday from 10 AM to 5 PM around the Merrick railroad station. Merrick Chamber of Commerce
Why I’d put it on the list: Carnival for the kids + a substantial street fair for the grown-ups = fewer negotiations over what everybody wants to do.
That alone deserves consideration. 😂
Syosset Street Fair | New Date: November 15
Where: Syosset
When: Sunday, November 15, 2026
This is exactly why I keep checking event information before sending you somewhere.
The Syosset Street Fair was originally scheduled for September 27, but organizers canceled the September event because of expected weather and moved it to its official rain date:
Sunday, November 15, 2026.
The Westbury Street Fair scheduled for September 26 was canceled and has no replacement date. Nassau Arts & Crafts Fairs
So if you’re seeing the September date for Syosset floating around online:
November 15 is the current date.
Check Syosset Street Fair updates
Worth the Drive: Long Island Fall Festival in Huntington
Where: Heckscher Park, Huntington
When: October 9–12, 2026
Okay, we’re crossing into Suffolk County for this one — but there’s a reason.
The Long Island Fall Festival takes over Heckscher Park for four days over the holiday weekend with live entertainment, food, vendors, a carnival, and family activities.
The 2026 hours are:
Friday, October 9: 5–10 PM
Saturday, October 10: 11 AM–10 PM
Sunday, October 11: 11 AM–10 PM
Monday, October 12: 11 AM–5 PM
Street and park vendors, free children’s magic shows, youth performances, and more will also be happening throughout the weekend. Huntington Chamber
Why I’d make the drive: It’s one of those festivals where you could genuinely spend most of the day and still not see everything.
Long Island Fall Festival details
Which Long Island Fall Festival Should You Choose?
If you’re looking at this list thinking,
Rachel, I have approximately four free weekends, and you’ve just given me A LOT of places to go…
I know. 😂
Here’s the shortcut.
For a HUGE festival:
Oyster Fest or the Long Island Fall Festival.
For the classic Long Island street-fair experience:
Massapequa Park or Merrick.
For younger kids:
Long Beach Fall Festival.
For food + drinks + music:
Mineola Fall Festival.
For history + fall:
Rock Hall Country Fair.
For vendors and shopping:
Eisenhower Park or Merrick.
For a smaller community outing:
Franklin Square or Nassau Boulevard.
For North Shore fall vibes:
Oyster Bay.
No contest on the vibes. 😉
Before You Go to a Fall Festival on Long Island
There is one thing I want you to do before heading to ANY outdoor fall event:
Check it again that morning.
Fall events on Long Island are especially vulnerable to rain, wind, date changes, and last-minute cancellations.
We already saw it happen this year with Syosset and Westbury.
So even if you’ve had an event on your calendar for three weeks, take 30 seconds to check the organizer’s website or social media before loading everyone into the car.
Future you will thank present you.
More Fall Things to Do on Long Island
Street fairs are only the beginning.
If you’re ready for another quintessential fall day, check out my guide to apple picking on Long Island — including the orchards I think are absolutely worth the drive.
[INTERNAL LINK: Apple Picking on Long Island: Orchards Worth the Drive in 2026]
I’m also putting together separate guides for:
- Pumpkin picking on Long Island
- Fall farm fun
- Family-friendly Halloween events
- Haunted houses and scary attractions
- Fall food festivals
- Arts and craft fairs
- Fall hiking and foliage
- Free fall events
- October events on Long Island
- November events on Long Island
So yes…
Your fall calendar is about to fill up.
Frequently Asked Questions About Fall Festivals on Long Island
What are some of the best fall festivals on Long Island in 2026?
Fall festivals and street fairs happen across Long Island throughout the season. Some of the larger 2026 events include Oyster Fest in Oyster Bay, the Massapequa Park Village Street Fair, the Long Beach Fall Festival, the Mineola Fall Festival, the Merrick Fall Festival, and the Long Island Fall Festival in Huntington.
Are there free fall festivals on Long Island?
Yes! Many community fall festivals on Long Island have free general admission. Examples include the Massapequa Park Village Street Fair, Long Beach Fall Festival, Rock Hall Country Fair, and Nassau Boulevard Street Fair. Food, rides, and individual attractions may cost extra.
Where can I find fall festivals in Nassau County?
Nassau County hosts fall festivals and street fairs throughout communities including Oyster Bay, Mineola, Long Beach, Massapequa Park, Bethpage, Merrick, Franklin Square, East Meadow, West Hempstead and Syosset.
When are most Long Island fall festivals held?
The busiest stretch for Long Island fall festivals is generally late September through October, although some events continue into November.
Are there family-friendly fall festivals on Long Island?
Absolutely. Many Long Island fall festivals include children’s activities such as pumpkin patches, inflatables, rides, hayrides, crafts, costume parades, and live entertainment. Check the individual festival before visiting to see which activities have additional fees or age requirements.
Should I check an event before leaving home?
Yes. Outdoor fall events can be postponed, moved to rain dates, or canceled because of weather. Always check the official event website or organizer’s social media before leaving home.
Looking for More Things to Do on Long Island This Fall?
This is just the beginning.
I’m putting together my 2026 guide to fall on Long Island, with plenty of apple picking, pumpkin patches, festivals, Halloween fun, outdoor adventures, and seasonal things to do — including LOTS happening right here in Nassau County.
Hi! I’m Rachel Doppelt with North Star Realty Associates, and I share the places, events, neighborhoods, and local finds that make Nassau County such a great place to call home.
I’ll keep this guide updated with fall festivals on Long Island as new events and schedule changes are announced.
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