Long Island has a packed calendar year-round — from food festivals and outdoor concerts to holiday celebrations and sporting events. Here’s what to put on your radar.
Last updated: September 2026
Fall is one of the best times of year on Long Island — and one of the busiest seasons for buyers and sellers. Here is what is worth putting on your calendar across Nassau and Suffolk between now and the holidays.
45th Annual Italian Festival — North Hempstead Beach Park, 175 West Shore Road, Port Washington · September 10–13
Four days from the John Michael Marino Lodge, running since 1979. Meatball and eggplant heroes, the pasta and pastry tents, fresh zeppole, carnival rides, and fireworks Saturday night. Thursday and Friday 6–11 p.m., Saturday 2–11 p.m., Sunday noon–9 p.m.
Long Island Wine & Food Classic — Farmingdale State College · September 19
More than 25 restaurants and 20 beverage companies under one roof.
Valley Stream Community Fest — Arthur J. Hendrickson Park, Valley Stream · September 19
Over 200 vendors, live music, food trucks, and free parking. Drew more than 10,000 people last year.
Hicksville Chamber of Commerce Street Fair — Jerusalem Avenue, West John Street to Herzog Place, Hicksville · Sunday, September 20, 10:00 a.m.–4:00 p.m.
Free. The road closes for an 80-plus vendor craft and merchandise bazaar, inflatable rides, a rock wall, a food court, and a live DJ. Free ice cream for the first 500 children twelve and under.
Long Island Potato Festival — Farmingdale State College · September 26–27
Free admission. A potato food court, carnival, farmer’s market, live entertainment, and touch-a-tractor for the kids — a nod to the farming history that shaped this island.
East Northport Festival & Street Bazaar — Larkfield Road, Pulaski Road to Kew Avenue · September 12–13, 11:00 a.m.–6:00 p.m.
Free, rain or shine. A hundred craft artisans and merchandise vendors line Larkfield Road, with live music, street food, and the carnival running alongside.
46th Annual Pickle Festival — John Gardiner Farm, Greenlawn · Saturday, September 19
The Greenlawn-Centerport Historical Association’s fundraiser, and a genuine local institution. Pickles of every size, roasted corn, a corn maze, hay rides, and craft vendors.
12th Annual Dragon Boat Race Festival — Harborfront Park, Port Jefferson Village · Saturday, September 19, 8:30 a.m.–5:00 p.m.
Free. Bring a lawn chair and watch the heats from the harbor — plus Asian cultural performances, vendors, and food trucks all day.
Long Island Family Festival — Tanner Park, Copiague · September 25–27
Free and pet friendly, right on the bayside beach. Friday 6–10 p.m., Saturday 11 a.m.–10 p.m., Sunday 11 a.m.–8 p.m. Carnival, pet expo, and continuous live music.
Greenport Maritime Festival — Mitchell Park and the village waterfront, Greenport · September 26–27
Over 35 years running. Saturday opens with the parade, then wood boat displays, water sports demonstrations, model ship building, and music through the weekend.
17th Annual Over 50 Fair — Hilton Long Island/Huntington, 598 Broadhollow Road, Melville · Sunday, September 27, 10:00 a.m.–4:30 p.m.
Over 80 exhibitors and more than 20 classes — health, finance, downsizing, and living trusts among them. $7 in advance, $10 at the door, free for veterans with ID. If you are thinking about a move or helping a parent plan one, this is the single most useful day on the fall calendar. I expect to be there.
Seaford Oktoberfest — Seaford Train Station, along Sunrise Highway between Seamans Neck Road and Jackson Avenue · Saturday, October 3, 11:00 a.m.–5:00 p.m.
Free. Sixty-plus craft and merchandise vendors, a food truck rumble, a beer garden with four mobile bars, live music from the mobile stage, and a kids funzone with inflatables and a rock wall.
St. James Day — Lake Avenue, St. James · Sunday, October 4, 11:00 a.m.–5:00 p.m.
Free. Lake Avenue closes to traffic from Woodlawn Avenue to the St. James train station for more than 100 vendors, food booths, live music, a bounce house and a mechanical bull. Run by the St. James Chamber of Commerce.
Massapequa Park Village Street Fair — Massapequa Park · Sunday, October 4, 10:30 a.m.–4:30 p.m.
One of the largest on the island. Three live bands all day, a giant craft bazaar with more than 200 vendors, the Foodie Fest food truck rodeo, a mechanical bull, a rock wall, the Pequa Choo-Choo Express, and the Islanders slapshot booth. Free admission.
Famous Food Festival — Tanger Outlets Deer Park, 152 The Arches Circle · October 9–12
More than 100 food, beverage and artisanal vendors. Friday 1–8 p.m., Saturday through Monday 11 a.m.–8 p.m. Ticketed — buy early for the better price. The LIRR Ronkonkoma branch runs a shuttle from Deer Park station.
The Oyster Festival — Theodore Roosevelt Memorial Park & Audrey Avenue, Oyster Bay · October 17–18, 11:00 a.m.–6:00 p.m.
One of our favorites — the shucking contests, the food, the whole waterfront hamlet turned out for the weekend. Shuttles run between the park and Audrey Avenue. If you have never been, this is the one to go to.
Nassau Boulevard Street Fair & Foodie Fest — Nassau Boulevard at Hall’s Pond, West Hempstead · Sunday, October 18, 10:00 a.m.–4:00 p.m.
Free. A quarter-mile of craft vendors overlooking the pond, plus the Foodie Fest food truck show, a kids funzone, and live music. Hosted by the West Hempstead Community Support Association.
Spookyfest — Center for Science, Teaching & Learning at Tanglewood Preserve, Rockville Centre · weekends in October
A haunted woods walk with jump scares for older kids, and a separate non-scary enchanted garden for the little ones.
Tanger Outlets Holiday Festival & Tree Lighting — Tanger Outlets, Deer Park · Saturday, November 21, 2:00–6:00 p.m.
Santa arrives by fire department escort, there are ice skating performances and food trucks, and the rink opens to the public at 6:30. A reliable start to the season.
Village tree lightings across Nassau and Suffolk are announced through late October and early November. I will add them here as the dates are set.
St. Kilian’s Holiday Fair — St. Kilian’s Auditorium, 50 Cherry Street, Farmingdale · December 5–6, 10:00 a.m.–4:00 p.m.
Expanded to two days this year. A hundred artisans and vendors, an all-day DJ, free face painting, and free photos with Santa. Rain or shine, and a good one to know about early if you are shopping for handmade gifts.
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For the most up-to-date event information, check these resources:
Living on Long Island means there’s always something to do — whether you’re catching a summer concert at Jones Beach, exploring a fall festival on the North Fork, or celebrating at a downtown New Year’s Eve party.
Ready to make Long Island home? Learn more about me or get in touch to start your search.
Single-family homes, end of August 2026:
Nassau County — 3.2 months of supply, 23 days on market, 100.3% of asking
Suffolk County — 3.3 months of supply, 21 days on market, 102.9% of asking
Six months is the line between a buyer’s market and a seller’s market. Both counties sit at about half of that, so sellers currently have the stronger hand.
I explain what these three numbers actually mean, and why your town may look nothing like the county figure, here.
If you want to know what the numbers look like for your street, email me at carolyn@bestnyrealestate.net or browse current listings across Nassau, Suffolk, Queens and Brooklyn on my search page.
Source: OneKey MLS, InfoSparks. Single-family homes, August 2026.
