Looking for things to do on Long Island this weekend, October 10–11? It's Columbus Day weekend, Monday is off for most Long Island schools, and that changes the whole picture. The Islanders are home tonight against Tampa Bay, the Hamptons International Film Festival is in its final weekend, and the East End farms are as busy as they get all year. Saturday should be the nicer day, mostly cloudy with a high near 69. Sunday looks wetter, with showers moving in after about 2 p.m., so plan your outdoor stops for the morning.

A three-day weekend in October also means the roads east of Route 111 will be crowded from Saturday morning on. Here's what's worth the trip and how to get there without losing half your day to traffic and parking.

Islanders vs. Tampa Bay Lightning — UBS Arena, Elmont

Saturday, October 10, 7:30 p.m. | UBS Arena, Belmont Park, Elmont

It's the third home game of the season, a week after the home opener against the Devils. Tampa Bay is always a good draw at UBS. A Saturday night game on a holiday weekend means a full building and a lot of families who don't have to get up early Monday.

You know what Saturday games at Belmont are like. The Cross Island backs up at the Hempstead Turnpike exit by 6:45, and the lots closest to the arena fill first. After the final horn, 17,000 people all try to leave the same few exits at once. From Huntington or Commack, getting home can take longer than the third period. We drop you at the door and pick you up at a set spot after the game, so you skip the lot entirely. We run Nassau County every day and know how this building empties out. There's another home game Tuesday night against Vancouver if Saturday doesn't work.

Hamptons International Film Festival, Closing Weekend — East Hampton, Sag Harbor and Southampton

Through Monday, October 12 | Guild Hall, Sag Harbor Cinema, Southampton Playhouse and other venues

The 34th HIFF wraps up Monday, so this is the last weekend to catch it. The closing days usually bring the award-winner encore screenings and some of the hardest tickets of the festival. Check hamptonsfilmfest.org for the final schedule before you head out, since some screenings sell out ahead of time.

The festival is spread across three villages, and getting between them is the hard part. On a holiday weekend, Route 27 through Bridgehampton is slow by midday Saturday. Parking on Main Street in Sag Harbor or Newtown Lane in East Hampton is close to impossible in the afternoon. And if you're driving home to Nassau or western Suffolk after a late screening and a drink, that's two hours on Sunrise Highway in the dark. Our Hamptons car service lets you book a driver by the hour for the day. You go from theater to theater and never have to find a parking spot.

The Great Pumpkin Palooza at Lenny Bruno Farms — Manorville

Saturday and Sunday, 10 a.m. to 5 p.m. | Lenny Bruno Farms, 740 Wading River Road, Manorville

This is one of the biggest family fall days on the East End. There's pumpkin picking, a corn maze, hayrides, bounce houses, lawn games, live music and eating contests. Saturday is the better bet with rain likely Sunday afternoon.

Manorville sits right where the LIE ends and traffic for the East End starts to build. On Columbus Day weekend, everyone going out for pumpkins and apples takes the same exits. Exit 70 and Wading River Road back up by late morning, and so do Sound Avenue and Route 25 farther east. If you've got a car full of kids and pumpkins, it helps to have someone else doing the driving. If the adults want to stop at a North Fork tasting room on the way home, the farm stands and wineries are only 15 minutes up the road. With a driver, nobody in your group has to stay sober to get everyone home. Our hourly service is built for that kind of day.

Honoring the Vanderbilt Racing Legacy Car Show — Centerport

Sunday, October 11, 11 a.m. | Suffolk County Vanderbilt Museum, 180 Little Neck Road, Centerport | $10–$15

The Vanderbilt Museum is hosting a classic car show on its grounds, with Jaguars, Porsches, Mustangs and more parked on the lawn above Northport Bay. It's a nod to William K. Vanderbilt II, who started the Vanderbilt Cup races on Long Island in 1904. Those races ran right through Nassau and Suffolk, and the Long Island Motor Parkway was built for them.

The estate is a beautiful place to spend a fall morning, and it's worth getting there early before Sunday's rain. The museum sits at the top of a winding road off 25A, and parking on car show days is tight. Centerport is close if you're coming from Huntington or Dix Hills. It's a real drive from the South Shore or Nassau, though, and a car service lets you walk the show and take your time without worrying about the lot.

Five for Fighting — Landmark on Main Street, Port Washington

Saturday, October 10, 8 p.m. | Landmark on Main Street, 232 Main Street, Port Washington | about $57

John Ondrasik and Five for Fighting play a small North Shore theater on Saturday night. "Superman" and "100 Years" are the kind of songs that sound better in a room this size than they ever did on the radio.

Port Washington's Main Street is a great night out, with dinner along the water before the show. The catch is parking. The Main Street lots fill fast on Saturday nights, and the town lot by the LIRR station is a walk. If you're coming from Suffolk, it's a long trip west on the Northern State and back late at night. Book a car for dinner and the show and you won't have to deal with any of that.

Sunday Rainy-Day Backup: Long Island in the '70s at the Long Island Museum — Stony Brook

Long Island Museum, 1200 Route 25A, Stony Brook | The Long Island Music & Entertainment Hall of Fame is up the street at 97 Main Street

If the rain shows up on schedule Sunday afternoon, Stony Brook is a good indoor option. The Long Island Museum's "Long Island in the '70s" exhibit is a fun look back for anyone who grew up here. Down Main Street, the Long Island Music & Entertainment Hall of Fame has rock band Blue Light Effect playing a free-with-admission set at 3 p.m. Add a late lunch in Stony Brook Village and you've got a full rainy afternoon.

Stony Brook Village gets busy on holiday weekends, and the drive back west on 25A or Nesconset Highway in the rain isn't anyone's idea of fun. A driver takes care of it.

Also on This Weekend

Carolyn Wonderland plays blues at the YMCA Boulton Center in Bay Shore Saturday at 8. "Spookley the Square Pumpkin: The Musical" opens at the CM Performing Arts Center in Oakdale Saturday at 10 a.m., with a sensory-friendly show Sunday. The 7th annual Commack Day Festival is Sunday from 11 to 4 at the Suffolk Y JCC on Hauppauge Road. Connetquot River State Park Preserve has free haunted house storytelling walks Saturday night (ages 10 and up). In Bridgehampton, SoFo is celebrating the Long Pond Greenbelt on Saturday morning with bird walks and animal encounters for kids. LuminoCity Dino Safari is at the Walt Whitman Shops in Huntington Station through October 18.

Coming Up Next Weekend

October 16–18 is the big one. The Oyster Bay Oyster Festival expects close to 200,000 people at Theodore Roosevelt Memorial Park, and the Greenport Maritime Festival, which the September nor'easter pushed back, now lands on the same weekend. Parking near both will be very limited. If you know you're going, it's worth booking now.

Getting Around Long Island This Columbus Day Weekend

Three-day weekends in October are some of the busiest of the year out here. You've got a sold-out arena in Elmont, a film festival across three villages and every farm stand from Manorville to Orient full of people. A lot of your weekend can end up being spent in traffic or looking for parking.

We've been driving these roads for 20 years. We know when the Cross Island backs up before a game, how long the LIE really takes past Exit 70 on a holiday Saturday, and how to get out of Sag Harbor after a screening. You shouldn't have to think about this. See our Long Island car service page, or request a quote and we'll handle the rest. The car will be there.

Best Things To Do on Long Island This Weekend — October 10–11, 2026