This is the first real summer weekend on Long Island, and the East End is wide awake. Strawberry season just opened on the Manorville farms, the dogs are flying off the dock in Greenport, the North Fork tasting rooms are full, and the Jones Beach concert season is kicking off in Wantagh. The weather has turned, the Hamptons social season is in full swing, and the calendar is finally giving you reasons to get out of the house.

One housekeeping note up front for the racing fans: it's Belmont Stakes day, but the race is not on Long Island this year. With Belmont Park still under construction, the 2026 Belmont Stakes runs at Saratoga (post time 7:04 PM). So don't point the car toward Elmont expecting a race. Here's what's actually worth planning around close to home this weekend, with the parking and traffic reality for each.

Strawberry Festival — Lenny Bruno Farms, Manorville

Saturday, June 6 + Sunday, June 7 | 10:00 AM – 5:00 PM | 740 Wading River Road, Manorville

Lenny Bruno Farms runs its 5th annual Strawberry Festival across this weekend and next, and it's the family anchor of the weekend. Admission is $10 (kids 2 and under free), and it gets you live music, a foam bubble party, playgrounds, jumbo garden games, farm animal meet-and-greets, face painting, and a row of artisan vendors and food trucks. The real draw is the pick-your-own strawberries out in the fields, which the farm only opens for these two June weekends.

Manorville sits at the eastern end of Suffolk, right where the LIE runs out and the roads narrow toward the forks. From central Nassau you're looking at 45 minutes to an hour, and a sunny festival Saturday fills the farm lot fast, with the overflow spilling onto Wading River Road. For a family making the drive out with young kids, a car service drops you right at the gate and picks you up when the kids are sticky, sun-worn, and carrying a flat of strawberries. Nobody's circling for parking.

10th Annual North Fork Dog Dock Diving Weekend — Greenport

Saturday, June 6 + Sunday, June 7 | All day | The Polo Grounds, Greenport

This one is exactly as fun as it sounds. The North Fork Dog Dock Diving Weekend hits its 10th year at the Greenport Polo Grounds, and it's a full DockDogs competition: dogs sprinting down a dock and launching into the water for Big Air, racing the clock in Speed Retrieve, and going sky-high in Extreme Vertical. There's something happening every few minutes, plus kid-friendly fun, local vendors, food, and a beer garden. A portion of the proceeds supports the Greenport Skate Park, and this year's milestone event is a designated Wild Card, so competitors earn double points.

Greenport sits at the tip of the North Fork, a good haul from anywhere west of Riverhead. Route 25 through Cutchogue, Peconic, and Southold is the only real way in, and it gets busy on a summer Saturday as wine-trail and ferry traffic stacks up. Downtown Greenport parking is tight in season even without an event. If you're making a North Fork day of it, this pairs naturally with a couple of tasting rooms, which is exactly the kind of day where a driver earns their keep.

North Fork Wine Country — Fully in Season

Saturday, June 6 + Sunday, June 7 | Across the North Fork wine trail, Mattituck to Southold

The North Fork is humming now. Sannino Vineyards hosts the Perfect Strangers guitar-and-flute trio on Sunday at 1:00, Rose Hill Vineyards runs a "plant a mini herb garden" workshop Sunday at 11:00, and the Greenport Farmers Market is on Saturday from 9:00 to 1:00 with wine, produce, seafood, and baked goods. Friday night kicks the weekend off with First Fridays on Love Lane in downtown Mattituck. The whole Main Road from Mattituck to Southold is one tasting room after another, a few minutes apart.

The North Fork is the clearest transportation case we run all summer. A real day on the wine trail means three or four tasting rooms, and somebody in the group always ends up being the designated driver instead of enjoying it. The Main Road is dark and narrow at night, the drive back west is long, and a DWI out here is a risk people talk themselves out of worrying about until it's too late. We run wine-country days constantly: one car for the group, a route planned around the wineries you actually want, and everyone gets to drink. Our Sprinter van service handles groups of six to fourteen for exactly this.

Jones Beach Theater — Concert Season Opens

This weekend + all summer | Northwell at Jones Beach Theater, Wantagh

The Jones Beach concert season is officially underway. The 2026 summer lineup is loaded — Dave Matthews Band, Chris Stapleton, Rod Stewart, Tim McGraw, Santana, The Beach Boys, and more across the season — and the early-June shows are the start of three months of nights on the water in Wantagh. Even on a weekend without your specific headliner, the venue and the beach around it are the South Shore's summer center of gravity.

Jones Beach parking is the part nobody enjoys. Field 4 fills, the Wantagh Causeway backs up before and after every show, and getting out of the lot when the crowd leaves all at once is its own special test of patience. For a date night or a group heading to a concert, a drop right at the gate and a pickup that skips the post-show parking-lot crawl is the whole point. You walk out, the car's there, and you're home while everyone else is still inching toward the causeway.

The Hamptons — Social Season in Full Swing

All weekend | Southampton, East Hampton, Sag Harbor, Montauk

The Hamptons season opened Memorial Day weekend, and it's now the everyday reality straight through Labor Day. The restaurants, beach clubs, and village downtowns are running full summer programming, the polo and charity calendar is filling up, and the East End is in its rhythm. There's no single must-do anchor this particular weekend, but the whole region is alive — and the Sunrise Highway has settled into its summer pattern.

That pattern is predictable and worth planning around: eastbound crawls Friday afternoon and Saturday morning, and the Sunday evening westbound return between 4:00 and 8:00 is the same jam in reverse. A couple heading out for a weekend in Sag Harbor or Montauk gets the round trip handled instead of fighting the Sunrise both ways. Groups renting an East End house book a single drop and pickup, plus the JFK or LGA run when the weekend wraps. The traffic only gets heavier from here.

Getting Around Long Island This Weekend

The Nassau parkways and the western LIE stay manageable this weekend — the action is east. The pressure builds the further out you go: Sunrise Highway eastbound toward Manorville and the forks Saturday morning, Route 25 through the North Fork toward Greenport, and the Wantagh Causeway around any Jones Beach show. The Sunday evening westbound return from the East End is the predictable slow stretch.

For the Strawberry Festival in Manorville and dog dock diving in Greenport, give yourself extra time eastbound and expect a parking hunt at both. For a North Fork wine day, the smart move is not driving at all. For Jones Beach, the headache is the lot, not the drive.

We cover all of it — airport transfers, corporate travel, and weekend trips out on Long Island. Whether it's a North Fork wine-trail day, a family run out to the strawberry fields with a pickup when the kids are done, a Jones Beach concert night that skips the causeway crawl, or a Sunday ride home from the Hamptons that beats the Sunrise traffic, the process is the same. Request a quote here and we'll handle the rest.

Best Things To Do on Long Island This Weekend — June 6–7, 2026