Hamptons in the offseason: Summer hot spots without the crowds

Hugh King grew up in East Hampton in the 1950s. The lifelong resident, who is both East Hampton town and village historian and director of the Home Sweet Home Museum, watched the area transform as the place to be from Memorial Day to Labor Day. Every summer, the area’s villages and hamlets draw some of New York’s trendiest to eat, swim and sun. Even driving in the area in season can be impossible, he said.

"It’s difficult to get around. You can’t really get a restaurant reservation. Most of the full-time residents just stay home, but once the season’s over, everything changes," he said.

Take advantage of the lighter crowds and lingering warm weather with a day trip to the area. Come for the award-winning beaches and stay for the farms, vineyards, events and restaurants.

Sun and sand in the offseason

East End beaches consistently make national best beaches lists. Southampton’s Coopers Beach and Main Beach in East Hampton have ranked among Dr. Beach's Top 10 Beaches' list annually. During the summer, a day parking pass is $55 at Coopers Beach and $50 at Main Beach — and that’s if you can get a spot. But visiting offseason means you get access without the crowds and park for free. Keep in mind that there are no lifeguards on duty.

If you're looking to catch a wave, Hamptons Surf Co. offers private and semiprivate lessons year-round starting at $130 per person, including surfboards and wetsuits.

Go to a fall fair or festival

If you like a little structure to your visit, festivals provide excitement when things are quieter.

The Sag Harbor American Music Festival (Sept. 24-27) has three main stages where you can hear jazz, blues, salsa, country and rock artists. Music spills out to the rest of the town, too.

Catch performances at St. David AME Zion Church, Sag Pizza, Amy’s Music Store, Provisions Market & Cafe and at parks. The best part: Nearly everything is free. There are 40 performances that won’t cost you a dime. There’s one ticketed headliner, Grammy-nominated guitarist Raul Midón, who plays Sept. 25 at Bay Street Theater ($62.11).

In October, you can hit the Hamptons International Film Festival (Oct. 2-12). The HIFF is 11 days’ worth of screenings, panels, parties and events, according to the organizers. While a Founders Pass all-in ticket costs $2,500, there’s an Out East package ($180) that gets you 10 tickets to general film screenings.

Make your way to "The End," for free, family-friendly annual Montauk Fall Festival (Oct. 10-11). Open from 11 a.m. to 5 p.m., there’s a farmers market, kids activities, band performances and a silent auction, along with a clam-chowder-eating contest Oct. 10.

Head to a farm or winery

Farms and vineyards also highlight the trades in the Hamptons.

Hank's Pumpkintown in Water Mill offers corn mazes, games, slides, wagon rides and apple-picking. Wear good shoes and go early before everyone else makes a day of it.

Amber Waves, a nonprofit teaching farm, is less crowded and open daily at 8 a.m. for self-guided tours, including of the flower fields and to visit the farm's chickens. Its kitchen and espresso bar are open and there are often programs running.

Visitors over 21 may prefer a wine day. There are three wineries to check out in the Hamptons: Channing Daughters Winery, Duck Walk Hamptons  and Wölffer Estate Vineyard. Wölffer Estate has sunset music Saturdays in September and October.

Check out live music or grab a bite

After dark, don’t sleep on The Stephen Talkhouse intimate venue in Amagansett. Singer John Mayer played the annual SiriusXM concert in August. The venue schedules music and events on occasional Thursdays and every Friday and Saturday this fall.

After a busy day, you’ll need sustenance, and Hamptons restaurants are legendary. Although some of the hottest spots close in the fall, there are options for breakfast, lunch and dinner not to miss. Lunch Lobster Roll is one option.  The restaurant, with locations in Amagansett and Southampton, switches over to its fall/winter hours, staying open 11:45 a.m. until 8 p.m. Thursday through Sunday.

"The crowds disperse and pretty much any restaurant is enjoyable and everyone is really happy to see you," said Cassie Esposito, a real estate salesperson at Compass in East Hampton. 

In addition, you’ll want to try Nick & Toni’s and East Hampton Grill, which are almost impossible to get into over the summer. Both take reservations online. Sag Harbor’s Le Bilboquet, another tough reservation, also stays open weekends until the end of October. In Bridgehampton, Jean-Georges at Topping Rose House is a coveted summer farm-to-table restaurant worth trying after Labor Day. The restaurant serves breakfast, lunch and dinner and welcomes families as well as serious foodies.

Stay overnight 

While you can drive out east for a day trip, you can spend a night too. For an overnight, options include Topping Rose House, which — aside from Jean-Georges — also houses a 22-room luxury hotel, spa and fitness center. Another upscale option, the luxury Roundtree Amagansett (from $833), includes continental breakfast, afternoon tea, evening snacks, access to bicycles and pet amenities.

Another family- and pet-friendly option is the Southampton Inn (from $322), which has lawn games, outdoor televisions, a pool bar and heated pool, and tennis and pickleball courts. The budget-friendly Atlantic Hotel in Southampton (from $119) is still luxe enough so you can pretend you’re a local.