Retro Games, Country Nights & Vineyard Flights: The Long Island Weekender for August 8–11; Top Long Island Events
LONG ISLAND, NY – From Friday, August 8, through Monday, August 11, Long Island comes alive with diverse entertainment: concerts at Jones Beach, vintage gaming nostalgia, outdoor family fun, artisanal markets, and scenic escapes in the Hamptons and East End wineries. Whether you’re craving live music, community fairs, or sunset wine views, this lineup has it all.
Long Islanders and visitors alike can dive into immersive exhibits, kick back at free concerts in community parks, or hop aboard a sunset cruise in Babylon. For families, it’s a golden opportunity to entertain the kids with hands-on workshops and dino-sized adventures. And for couples or day-trippers, the East End is calling with beaches, boutiques, and beautiful vineyard escapes. This edition of The Weekender is your go-to resource to craft the perfect summer escape, right here at home.
Gaming & Geek Culture
- Long Island Retro Gaming Expo at Cradle of Aviation Museum, in. Garden City. Fri Aug 8 (3 pm–9 pm), Sat Aug 9 (10 am–9 pm), Sun Aug 10 (10 am–5 pm). Celebrate 40 years of the NES and classic gaming culture. Expect arcade setups, vendor booths, panels, and interactive demos over the weekend.
Music & Concerts
- Town of Hempstead Free Concert Series
Fri Aug 8 at 7:30 pm, Merrick Road Park, Merrick – a relaxed, free community concert to kick off the weekend. - Little Big Town – Summer Tour at Jones Beach Theater Sat Aug 9 – renowned country-pop hits under the night sky.
- The Doobie Brothers + Coral Reefer Band at Jones Beach Theater Sun Aug 10 – classic rock legends performing as part of their ‘Walk The Road Tour‘
Family & Outdoor Fun
- Exhibit: Dinosaurs: Fossils Exposed at Long Island Children’s Museum Daily Aug 8–11 at 10 am – explore giant fossils and interactive displays.
- Movie Nights at Eisenhower Park – Fri & Sat evenings – free outdoor movie screenings that get rolling after sunset.
- Bay Cruise on the Great South Bay at Captain Gillen, Babylon Fri Aug 8 at 8 pm – scenic, family-friendly evening cruise (no fishing).
- Build‑a‑Boat Workshop at Whaling Museum, Cold Spring Harbor Sat Aug 9, 11 am–1 pm – families design and sail miniature boats and solve scavenger hunts.
- Family Movie Matinee at Island Trees Public Library, Levittown Sun Aug 10, 2:30 pm–4:30 pm – indoor cozy film fun for kids.
Arts, Markets & Local Life
- Arts in the Plaza Market at Kennedy Plaza, Long Beach Sat Aug 9, 9 am–2 pm (weekly through Oct.) — crafts, live music, local artists, free admission.
Wine Country & Hamptons Escapes
- East End Vineyard Getaway August weekend day-trip option – visit renowned vineyards like Wölffer Estate or Macari in Sagaponack / North Fork. Wine tastings, live music, serene vineyard grounds, and seasonal food trucks.
- Hamptons Day Excursion Saturday or Sunday option – explore towns such as Sag Harbor, East Hampton or Montauk. Highlights: Parrish Art Museum, Montauk Point Lighthouse, boutique shopping, and seaside dining in uncrowded stretches.
Sample Itinerary: A Perfect Long Island Weekend
Friday, August 8
🕕 5:30 PM – Arrive in Garden City for opening night at the Long Island Retro Gaming Expo. Play vintage arcade games and browse collectibles.
🕗 8:00 PM – Head to Merrick Road Park in Merrick for a free outdoor concert. Bring a blanket and enjoy live music under the stars.
Saturday, August 9
🕘 9:00 AM – Start at Arts in the Plaza in Long Beach. Browse handmade crafts and enjoy acoustic performances.
🕚 11:30 AM – Stop by the Whaling Museum in Cold Spring Harbor for the Build-a-Boat Workshop – great for kids and curious adults alike.
🕓 4:00 PM – Make your way to Jones Beach for tailgating before the Little Big Town concert.
🕗 7:30 PM – Showtime at Northwell Health at Jones Beach Theater.
Sunday, August 10
🕘 10:00 AM – Visit the final day of the Retro Gaming Expo or explore the Dinosaurs: Fossils Exposed exhibit at the Long Island Children’s Museum.
🕐 1:00 PM – Grab lunch in Garden City or head east for a wine tasting at Wölffer Estate Vineyard in Sagaponack.
🕖 7:00 PM – End the night back at Jones Beach with The Doobie Brothers and Coral Reefer Band.
Monday, August 11
🕘 9:30 AM – Take it slow with coffee and a stroll in Sag Harbor Village.
🕚 11:00 AM – Visit the Parrish Art Museum in Water Mill for a final touch of culture.
🕐 1:00 PM – Lunch on the water in Montauk or Greenport before heading home.
