Guides · Updated August 2026
The Island’s best season
Summer people leave, farm stands peak, and every weekend has three festivals. This guide regenerates from our live data, so the dates you see are this year’s, verified.
Farms, mazes, and pick-your-own
Cider donuts are a fall food group.
Harbes Family Farm
Mattituck
White Post Farms
Melville
Hank's PumpkinTown
Water Mill
Lewin Farms
Wading River
The Milk Pail
Water Mill
Wickham's Fruit Farm
Cutchogue
Amber Waves Farm
Amagansett
Catapano Dairy Farm
Peconic
Corwith Farmstand
Water Mill
Crossroads Farm at Grossmann's
Malverne
Foliage worth a drive
Peak color, no Vermont traffic.
Outdoors Massapequa Preserve
Massapequa
Prosser Pines Nature Preserve
Middle Island
Outdoors Caumsett State Historic Park Preserve
Lloyd Harbor
Garden Planting Fields Arboretum
Oyster Bay
Bayard Cutting Arboretum
Great River
Outdoors Connetquot River State Park Preserve
Oakdale
Outdoors Argyle Park
Babylon Village
Avalon Nature Preserve
Stony Brook
Fall events with real dates
Festivals, Oktoberfests, and haunted everything.
Shinnecock Indian Powwow
Southampton · Labor Day weekend, Sept 4-7, 80th annual
One of the top powwows in the country, right on the Shinnecock territory: dancers and drummers from across Indian Country, Native food and art.
Harbes Fall Festival Weekends
Mattituck · Festival weekends kick off Sept 12-13 with the Apple Festival, then run through October
Corn maze, pumpkin picking, pig races, cider donuts. Peak North Fork fall.
Long Island Garlic Festival
Riverhead · Sept 12-13 at Garden of Eve farm
A whole farm weekend devoted to the stinking rose: garlic everything, hay rides, corn maze, and a scavenger hunt on Sound Avenue.
San Gennaro Feast of the Hamptons
Hampton Bays · Sept 12-13 on Good Ground Road · free
Zeppole, sausage and peppers, and live music. Little Italy energy, Hampton Bays zip code.
Hicks Nurseries Fall Festival
Westbury · Daily Sept 12 through Nov 1; weekend activities with Otto the Ghost · free
The 51st year of Otto the Ghost, pumpkins, and cider donuts at Long Island's oldest garden center. Free admission, free parking.
East Northport Street Bazaar
East Northport · Sat-Sun, Sept 12-13, 11am-6pm on Larkfield Road · free
Larkfield Road shuts down for two days of vendors, food, and neighborhood wandering. The unofficial end of summer up north.
Babylon Village Annual Fair
Babylon · Sunday, Sept 13, 8am-5pm at Argyle Park (rain date Sept 20) · free
325+ craft vendors, a kids' zone at Bayman Park, and fresh-baked pies around the gazebo. The Beautification Society has this down to a science.
Bellmore Family Street Festival
Bellmore · Sept 18-21, carnival Friday night through the holiday-sized weekend · free
One of Nassau's biggest street fairs takes over the blocks by the Bellmore LIRR: hundreds of vendors, rides, and live music.
Bayville Scream Park
Bayville · September 18 through November 7, select nights; peak October weekends sell out
Six haunted attractions crammed onto the Gold Coast waterfront, and the lines on October Saturdays prove it. Buy timed tickets early or pay for your procrastination.
Cow Harbor Day Weekend
Northport · Great Cow Harbor 10K Saturday Sept 19; parade and harbor festival Sunday Sept 20 · free
Elite runners fly down Main Street on Saturday, then the whole village turns out Sunday for the parade and park festival. Northport's best weekend.
Port Jefferson Dragon Boat Race Festival
Port Jefferson · Saturday, Sept 19, 8:30am-5pm at Harborfront Park · free
Dragon boats thundering across the harbor all day, with food vendors and live music on shore. The 12th year of Port Jeff's loudest tradition.
Sag Harbor HarborFest
Sag Harbor · Sat-Sun, Sept 19-20 on the waterfront · free
Whaleboat races off Windmill Beach and a village that still remembers it was a whaling port. Sag Harbor's scrappiest weekend.