Embrace the Autumnal Splendor of Long Island's Wine Country

As the leaves begin to turn and the air grows crisp, Long Island's wine country comes alive with a vibrant array of fall festivities. From pumpkin painting to cider sipping, this weekend promises a celebration of all things autumn that's not to be missed.

Discover the Delights of the Season in Long Island's Picturesque Vineyards

Celebrate the Changing of the Seasons at The Pridwin Hotel and Cottages

For the first time in its 100-year history, The Pridwin Hotel and Cottages on Shelter Island is hosting a fall festival on October 12 and 13. This weekend-long celebration of autumn will offer a plethora of classic fall activities, including pumpkin painting, sack races, and live music. Guests can also enjoy a bouncy castle, hayrides, pumpkin bowling, and even a bobbing for apples contest. The festivities will be complemented by delectable buffets featuring dishes like char-grilled clams and oysters, chicken roulade, and roasted winter squash. As the sun sets, guests can gather around a cozy bonfire for s'mores and hot cider, followed by a spooky movie screening in the outdoor Grove Theater.

Indulge in Autumn-Inspired Dining at Arthur & Sons

Arthur & Sons is now offering a $39.95 prix fixe menu that showcases the flavors of the season. Diners can start their meal with a choice of Caesar salad, house salad, meatballs, fried calamari, or fried mozzarella. For the main course, options include classic Italian dishes like chicken parmesan, spicy rigatoni, and spaghetti and meatballs. And no meal is complete without dessert, with a mini cannoli plate or gelato al cioccolato cup to end the evening on a sweet note. But the indulgence doesn't stop there – guests can also enjoy happy hour at the bar, with half-priced appetizers, $10 house wines, and $12 well cocktails.

Discover Daily Specials at La Fondita

For those craving a taste of the Southwest, La Fondita has unveiled a lineup of mouthwatering daily specials. On Mondays, fajita lovers can indulge in a plato de fajitas with their choice of chicken, shrimp, or carne asada. Thursdays bring tacos al pastor, featuring marinated pork cooked with pineapple. And the weekend is packed with even more delectable offerings, including chile relleno on Fridays, parilla mixta on Saturdays, and tacos de birria de res, birria de res, and quesabirria on Fridays, Saturdays, and Sundays.

Celebrate the Changing of the Seasons at the 43rd Annual Montauk Fall Fest

The 43rd Annual Montauk Fall Fest is taking place this weekend, offering a full day of local music, activities for all ages, and a chance to sample the best chowder on the East End. From 11 a.m. to 5 p.m., visitors can enjoy live band performances, a chowder contest on Saturday, a chance auction, a silent auction, a food tent, beer and wine, a farmers market, and a cash catch drawing on Sunday. Chowder enthusiasts can purchase their contest mugs at the Montauk Chamber of Commerce and Visitors Center starting at 9 a.m. on Saturday, with the contest kicking off at 10 a.m.

Savor the Flavors of Autumn at Breeze Hill Farm and Lulu Kitchen & Bar

For those looking to indulge in the bounty of the season, Breeze Hill Farm is hosting an Apple Gala on October 24th, featuring an orchard tasting, a menu by Kitchen Party, and a wine pairing by Macari. Meanwhile, Lulu Kitchen & Bar in Sag Harbor is offering a variety of autumn-inspired specials, including happy hour at the bar from 5-6:30 p.m., 25% off all bottles from their award-winning wine list on Wednesdays, and a brunch happy hour with $12 cocktails on Sundays.

Indulge in Asian-Inspired Flavors at Highway Restaurant & Bar

For those craving a taste of the East, Highway Restaurant & Bar is bringing back its popular Asian Night on October 17th, featuring a menu of delectable offerings such as shrimp buns, tuna sashimi, yellow fish curry, chicken udon, and Thai ribs. Guests can indulge in these mouthwatering dishes from 5-9 p.m.

Celebrate Oktoberfest at The Wine Room in Hampton Bays

The Wine Room in Hampton Bays is getting into the Oktoberfest spirit on October 12th, with tastings and special appetizers hosted by Mike Dolan, the division manager of B. United International Importers. The festivities will kick off at 3 p.m., and reservations are recommended by calling 631-251-8272.