If you're looking for things to do on Long Island this weekend, October 17–18, this is one of the biggest weekends of the fall. The Oyster Festival takes over Oyster Bay, Greenport finally gets the Maritime Festival the September nor'easter pushed back, and the PBR bull riders are at UBS Arena for three nights. Add a Sunday afternoon of Mozart in Brookville and you have a full weekend without going anywhere near the Midtown Tunnel.

A word on the weather first. Friday night's cold front brought rain and wind, and Saturday morning still has showers in the forecast, with northwest gusts around 25 to 35 mph and highs only in the low 50s. Sunday is the better day: sunny, lighter wind, highs in the mid to upper 50s. If you have a choice about which day to spend outdoors, pick Sunday.

The 43rd Annual Oyster Festival, Oyster Bay

Saturday and Sunday, October 17–18, 11 a.m. to 6 p.m. | Theodore Roosevelt Memorial Park, Oyster Bay | Free admission

This is the big one. The Oyster Festival is the largest waterfront festival on the East Coast and draws somewhere between 150,000 and 200,000 people over two days. This year more than a dozen Long Island oyster farmers are taking part, so the oysters on the half shell are actually local. There are shucking and eating contests, seafood courts, food trucks, a craft beer garden, more than 15 bands, an arts and crafts pavilion, and Newton Shows rides for the kids. On Sunday there's a sensory-friendly family hour from 10 to 11 a.m., before the crowds show up.

Here's the problem. Oyster Bay is a small hamlet at the end of a two-lane road, and it was never built for 150,000 visitors. Parking near the park is very limited. The town runs free shuttles from the Syosset LIRR station and James H. Vernon School, and the LIRR adds trains on the Oyster Bay Branch, but the shuttle lines get long by early afternoon and the return trip at 6 p.m. is everybody leaving at once. Route 106 and Berry Hill Road back up all the way to the Jericho Turnpike.

A drop-off as close to the festival as police will allow, and a pickup at a spot we agree on ahead of time, saves you the shuttle line and the hunt for your car in a Syosset lot. If your group plans to spend the afternoon at the beer garden, it also settles the question of who drives home. We've worked Nassau County for 20 years and we know which back roads into Oyster Bay stay open on festival weekend.

Greenport Maritime Festival, Greenport

Saturday and Sunday, October 17–18 | Mitchell Park, 115 Front Street, and throughout Greenport Village | Free

The 36th Maritime Festival was supposed to happen in September. The nor'easter pushed it to this weekend, and the North Fork has been waiting for it. Saturday starts with the maritime parade down Front Street at 11 a.m., followed by community rowing, a fishing derby, a pie-eating contest and a hot sauce competition. Sunday is the one to plan around: the fish-filleting contest, the Cardboard Boat Regatta at 12:30 p.m. and the Work Boat Race at 1 p.m. The Mudflats play a free show at the Railroad Museum of Long Island at 2 p.m. Sunday.

Greenport is about an hour and a half from Melville on a good day, and October on the North Fork isn't a good day. You're sharing Route 25 and Route 48 with pumpkin-picking traffic and the last of the harvest weekend wine crowd. Parking in the village fills up by late morning, and a lot of people plan a stop at a vineyard in Cutchogue or Peconic on the way home. That's the part where you want someone else driving. We cover Suffolk County from Huntington all the way out to Orient Point, and a North Fork day trip with a driver waiting is one of our most popular October bookings.

PBR Maverick Days, UBS Arena, Elmont

Saturday, October 17, 6:45 p.m. and Sunday, October 18, 1:45 p.m. | UBS Arena, 2400 Hempstead Turnpike, Elmont | tickets from about $35

The New York Mavericks, the PBR's local team, host their Maverick Days homestand at UBS Arena all weekend. It's professional bull riding, team format: the best riders in the world against bulls that weigh close to a ton, with the pyrotechnics and music that come with it. It's a big night out, and the Sunday matinee works well for families.

UBS Arena is easy to reach from the Cross Island Parkway in theory. In practice, the Belmont lots are a long walk from the doors, PBR parking is sold separately for each date, and after the event everyone empties onto the Cross Island and Hempstead Turnpike at the same time. With Saturday's wind and temperatures headed for the 40s by the time it lets out, a drop-off at the door and a pickup at a set spot is a lot better than walking a cold lot in the dark.

Brian Kilmeade, Flagstar at Westbury Music Fair, Westbury

Saturday, October 17, 8 p.m. | 960 Brush Hollow Road, Westbury | $41 to $118

The Fox & Friends co-host, who grew up in Massapequa, comes home to Westbury for an evening of stories, history and his take on the news. Westbury Music Fair is in the round, so even the back rows feel close, and with a Long Island native on stage the room is mostly locals.

A lot of people make a night of it with dinner in Westbury or Garden City first. Brush Hollow Road sits between the Northern State and the Meadowbrook, and the venue lot slows down after the show while everyone tries to merge onto the parkways at once. If dinner involves a bottle of wine, let us handle the driving.

The Knights with Emanuel Ax, Tilles Center, Brookville

Sunday, October 18, 3 p.m. | Tilles Center Concert Hall, LIU Post, 720 Northern Boulevard, Brookville

Emanuel Ax is one of the great pianists alive today, and he joins The Knights, the Brooklyn orchestra led by brothers Eric and Colin Jacobsen, for two Mozart piano concertos: No. 17 in G major and No. 25 in C major. The program opens with an overture by the Chevalier de Saint-Georges. A world-class soloist this close to home doesn't happen often.

Tilles is on the LIU Post campus off Northern Boulevard, Route 25A, which is a slow road on a Sunday afternoon in October with everyone heading out to the North Shore farm stands. The campus lots work, but they're a walk from the concert hall. For an older couple, or anyone dressed up for the afternoon, a drop at the front of the building makes the day easier. It's also an easy pairing with a late lunch in Roslyn or Glen Head afterward.

Also on this weekend

The 40th annual Rock Hall Country Fair runs both days, 11 a.m. to 5 p.m., at the Rock Hall Museum on Broadway in Lawrence. Admission is free. Hempstead Lake State Park holds a free Fall Fishing Festival on Saturday from 10 to 3. Out east, Riverhead Raceway does Halloween Havoc on Saturday, with a school bus demolition derby and trick-or-treating in the pits. At night, Steve Trevino does stand-up at Patchogue Theatre on Saturday at 8, and JohnnySwim plays the same stage Sunday at 7. Schmitt's Farm Haunt in Melville is open for anyone who wants a scare.

Getting Around Long Island This Weekend

Most of this weekend comes down to two things: one huge crowd on the North Shore and one long drive out to the North Fork. Neither one goes well if you're circling for parking or arguing about who's driving home.

Here's how we handle it. We set the drop-off and pickup points before you leave, so nobody is texting "where are you" from the middle of a crowd. Your chauffeur keeps an eye on traffic on Route 106, the LIE and Route 25 and adjusts the route. And if your afternoon in Greenport runs long, the car waits.

If you're flying out Sunday or Monday, the same applies. After a stormy Friday night, airlines are still catching up on delays, and we track every flight we're booked against. See our JFK car service page for how that works, or our Long Island car service page for everything else we do.

You shouldn't have to think about parking in Oyster Bay this weekend. Request a quote and the car will be there.

Best Things To Do on Long Island This Weekend — October 17–18, 2026