Fall on the East End: Fairs, Festivals, Food & Fun Fill the Season

Fall is here, and with it comes a bounty of seasonal flavors and celebrations. Make the most of the crisp days ahead with festivals, feasts and plenty of festive fun!

Hallockville Museum Farm located on the North Fork is thrilled to share their 44th Hallockville Country Fair on Saturday, Sept. 27 and Sunday, Sept. 28 from 10 a.m. to 4 p.m. This year’s fair will celebrate the museum farm’s 50th anniversary, offering half-price admission on Sunday morning from 10 a.m. to 12 p.m., a concert by the No Doubt World Famous Monday Night Band at 1 p.m., an artistic hand-blown glass pumpkin patch, historic cooking demonstrations, a horse-mounted drill team, a dog that paints and the popular mix of family-friendly farm activities, historical tours and folk arts and skills demonstrations. Contemporary music and food trucks will also be a part of the festivities, as well as historic cook Diane Schwindt cooking over an open fire, a traditional bread-baking demonstration and a beekeeping demonstration. An amazing bake sale will be open throughout the day on both days and the announcement of winners of their annual contest which declares the tastiest jam, the perfect potato and the most spectacular squash–including pumpkins!

The Second Annual Heart of Springs “SpringsFest 2025” will take place on Saturday, Oct. 4 from 4 to 7 p.m.! The community music festival will be taking place on the grounds of the Parsons Blacksmith Shop in the heart of Springs. The event offers classic fall fair atmosphere for families who are welcome to bring blankets and chairs to sit and enjoy music by local band REEB “Real East End Brass,” crafts from local businesses, yard games, a blacksmith demonstration, sea shanties from David Cataletto, an entertaining history lesson from “town crier” Hugh King, food from food trucks serving dinners, light snacks, soft drinks and desserts, as well as beer for purchase from Springs Brewery! The event is free, however donations are strongly encouraged and welcome where any proceeds from individual and sponsorship donations will cover cost for the event but ultimately go towards Heart of Springs’ goal to raise funds to help with maintaining and restoring historical buildings in the area. A rain date for the event will be Sunday, Oct. 5 from 2 to 5 p.m.

Setting up your plans for Halloween? Calissa will be hosting their Annual Costumes & Cocktails Halloween Party on Friday, October 31! Celebrate in style anytime from 5 p.m. till late with the bar open late, a festive atmosphere in the lounge featuring a live DJ and dancing all night long. Plus, guests who arrive in costume will be treated to a complimentary glass of bubbles! Seasonal specials and hot cocktails will be served throughout the night. Nothing is scarier than missing out on the Hamptons’ hottest Halloween party, make your reservations ahead of time to ensure you don’t miss out!

The Pridwin Hotel & Cottages pop up with Grand Banks, Manhattan’s celebrated oyster bar, offers an exclusive seasonal culinary collaboration running through peak oyster season. The waterfront resort’s dining program will feature some of Grand Banks’ signature offerings including Sailor Baby oysters, caviar hash browns, seafood towers, lobster rolls and nautically inspired cocktails. For more information, menus and reservations, visit the Pridwin website!

Bring the aloha on game day at Whales Tale in Hampton Bays! Make the newly opened restaurant and bar your football spot with $25 Kona Big Wave pitchers, $25 buckets of Michelob Ultra and $40 buckets of Nütrl vodka seltzers. Plus, ask the team how you can be entered to win a Kona paddle board! The restaurant also offers specials throughout the week including Taco Tuesday specials available all day and Taps and Apps are 50% off on Thursdays. Cheers!

Did you know?

Love to fish but hate the hassle of cooking what you caught? Street Food on the Green in Montauk will cook it for you! Bring in your catch and let the chefs do the rest. Join them for happy hour to make the night even more memorable, which is now extended to include Sundays during all NFL games as well! Beer is only $7, wine is $8 and well drinks are $10 with kitchen and sushi specials available as well.

Bits & Bites:

The Children’s Museum of the East End will host “All Things Apple” on Saturday, Oct. 4 from 10 a.m. to 10:45 a.m. where kids (ages 2 to 5) and parents will peel, chop, mix and munch on a sweet seasonal favorite. Enjoy freshly picked apples and sweet cinnamon smells while baking a warm treat! The cost is $15 for members and $35 for non-members. Visit their website to register.

Almond in Bridgehampton is bringing back their famous “Artists & Writers” dinner series on Monday, October 6 at 7 p.m. featuring artist Perry Burns! A three-course family style meal will be served with a glass of wine or draft beer, all for $59 including gratuity. Catch the end of their participation in Negroni Week as well through September 28.

Rowdy Hall is celebrating Oktoberfest through Oct. 5 with all-day bar specials, Oktoberfest beer pints and tasting flights and a rotating two-course fixed price menu at $42.

Food Quote: “The heat of autumn is different from the heat of summer. One ripens apples, the other turns them to cider.” — George Washington Carver