If you are looking for things to do on Long Island this weekend, September 19–20 is the weekend the Island stops pretending it is still summer and starts doing fall properly. HarborFest takes over Sag Harbor for two days, the Wine and Food Classic returns to Farmingdale, dragon boats race in Port Jefferson Harbor, and two farm festivals run out east and in Greenlawn. Beach traffic is gone. Village parking is about to be worse than beach traffic ever was.

Here is what is on, and the honest transportation picture for each.

Sag Harbor HarborFest — Sag Harbor

Saturday and Sunday, September 19–20 | Long Wharf, Marine Park and Steinbeck Park, Sag Harbor

The biggest thing happening on the Island this weekend is happening at the far end of it. HarborFest runs both days across Long Wharf and the waterfront parks, with the Fall Arts and Crafts Fair, live music, food and drink vendors, harbor cruises and the whaleboat races that have been the centerpiece of this thing for decades.

The race schedule is worth knowing if you are timing your day. Elimination heats go Saturday at noon and again at 3 p.m. Sunday opens with the Firefighters' Cup at 11:30, semifinals at noon, and the men's and women's championship races at 3:30. The Clam Chowder Contest is Saturday at noon on Long Wharf, $25 gets you the tasting and a 2026 HarborFest mug, and the clam shucking contest follows at 2.

Now the part every local already knows. Sag Harbor has maybe a few hundred village spots on a normal day, and HarborFest takes the Long Wharf lot itself out of the equation. Everything funnels in over the North Haven bridge or down Route 114, both one lane each way with nowhere to go. By 11 a.m. Saturday people are parking in Noyac and walking twenty-five minutes. Add a beer tent and a two-hour drive home to Nassau and the math gets simple. We run the Hamptons and the East End all season, and this is the trip where getting dropped at Main and Bay instead of hunting a spot changes the entire day.

The Long Island Wine and Food Classic — Farmingdale

Saturday, September 19, 6 to 10 p.m. | Farmingdale State College, Farmingdale

The Wine and Food Classic is back at Farmingdale State College, under an 80-by-200 foot tent, with more than 30 restaurants and food purveyors alongside North Fork vineyards, Long Island craft breweries, premium spirits and cocktails. Chef Eric LeVine, who runs 317 Main Street and Vico in Farmingdale, is curating the culinary lineup, and DJ CHEF is working the room. Every tasting is included with admission, which is the important detail.

Read that last sentence again. Unlimited pours, four hours, walk-around format. This is not a dinner you drive home from, and Farmingdale State sits right off Route 110, so you are on the 110 corridor or the Southern State on the way back either way.

From Melville, Plainview, Bethpage or Massapequa this is a fifteen-minute ride each way and the cleanest example on this list of a night that should not involve your own car.

12th Annual Port Jefferson Dragon Boat Race Festival — Port Jefferson

Saturday, September 19, opening ceremony 8:30 a.m., races from 9 a.m. to about 5 p.m. | Jeanne Garant Harborfront Park, 101A East Broadway, Port Jefferson

Twelve years in and still one of the best free days on the North Shore. Local and regional teams race three heats of dragon boats in the harbor, with 20-plus vendors, kids' crafts and entertainment all day. Bring a chair and post up along the waterfront.

Port Jeff on a festival Saturday is its own problem. The village sits at the bottom of a hill, the lots behind Main Street and down by the ferry fill before 10 a.m., and Bridgeport ferry traffic loads and unloads onto the same streets all day. Overflow parking puts you at the top of the hill, which is a fine walk down and a much less fine walk back up at 4 p.m. A drop at Harborfront Park and a pickup on East Broadway skips all of it. We cover Suffolk County end to end.

San Gennaro Feast at Lenny Bruno Farms — Manorville

Saturday and Sunday, September 19–20, 11 a.m. to 6 p.m. | 740 Wading River Road, Manorville | $10 all ages

Lenny Bruno Farms bills this as New York's only farm-to-truck Italian food festival, and the claim holds up. The vendors cook with produce grown in the fields you are standing next to. Two days of Italian food, live entertainment, local beer and wine, artisan vendors and farm activities for the kids.

Manorville is deep Suffolk, which is the whole point and also the catch. You come off the LIE around Exit 69 or 70 onto Wading River Road, two lanes of country road that was not built for a festival crowd. Parking is in a farm field, and a farm field after midweek rain is a farm field with tire ruts in it. From Nassau it is an hour-plus each way.

For a family group, or two families going together, a Sprinter van makes this one trip instead of a two-car convoy and a meet-up point that never works out.

46th Annual Pickle Festival — Greenlawn

Saturday, September 19, 10 a.m. to 4 p.m. | John Gardiner Farm, 900 Park Avenue, Greenlawn | $5, $3 members, free under 12

Forty-six years running. The Greenlawn-Centerport Historical Association puts this on at the John Gardiner Farm to mark the pickle industry that actually made Greenlawn's name in the late 1800s. Fried pickles, pickle sandwiches, roasted corn, a farm stand, hayrides, the historic Lollipop Farm Train, antique cars, craft vendors and live music.

Easiest yes on the list if you have kids and you live near Huntington. Parking is entirely street parking on Park Avenue and the residential blocks around it, and the neighbors have opinions about that by mid-morning. Get there at 10 or get dropped off.

Heritage Country Fair at the Smithtown Historical Society — Smithtown

Saturday, September 19, noon to 4 p.m., rain date Sunday | 211 East Main Street, Smithtown | Free, donations welcome

Historical reenactors, antique cars, a petting zoo, pony rides, face painting, a vendor market, food trucks and property tours across the Historical Society grounds. Free, and they encourage period dress if you are the kind of household that owns period dress.

Parking is across the street at 222 East Main with crossing guards walking people over. East Main is Route 25, busy on a Saturday afternoon regardless, and the crossing is the part to think about with small kids. Central enough that it pairs well with the Pickle Festival earlier in the day.

Also on this weekend

Eddie Griffin is at Flagstar at Westbury Music Fair Saturday at 8 p.m., $48 to $144. Patchogue Theatre has a Hispanic Heritage Celebration Saturday at 6 and Carl Palmer's ELP Legacy show Sunday at 7. The Paramount in Huntington has 1964 The Tribute Sunday at 7:30, which means New York Avenue at letout. Battle of the Decades puts three tribute bands on the Madison Theatre stage at Molloy in Rockville Centre Saturday at 7:30.

The Week Ahead

If you fly or commute into Manhattan, read this part. The UN General Assembly high-level debate opens Tuesday, September 22 and runs through Monday, September 28. The city has designated Monday the 21st through Friday the 25th as Gridlock Alert days. NYPD closes First Avenue from 42nd to 48th, restricts the cross streets between First and Second, and runs rolling FDR Drive closures for motorcades with almost no warning. East Side closures start Sunday and hold through Saturday the 26th.

Practically: every Midtown alternate gets absorbed, the Queens-Midtown Tunnel approach stacks up at hours that make no sense, and a car heading to JFK from Manhattan on Tuesday morning is not on the schedule your map app is quoting. We run this week every year and we build the buffer in before it becomes a problem. If you have meetings or flights next week, see our UN General Assembly car service page and get on the calendar now.

One more for next weekend: the Islanders host the Rangers Friday the 25th and the Devils Saturday the 26th at UBS Arena, both at 7:30. Those Belmont lots are prepaid and they empty at one speed.

We have been running these roads for 20 years, from Route 114 into Sag Harbor to the Port Jeff hill to the farm fields in Manorville, and we plan the drop and the pickup around how each of those places actually fills and empties. See our Long Island car service details, or request a quote and we will take it from there. The car will be there.

Best Things To Do on Long Island This Weekend — September 19–20, 2026