1. Pile in for Powwow The 80th annual Shinnecock Powwow, one of the largest Native American gatherings on the East End, comes to Southampton for Labor Day weekend. Featuring traditional dancing, singing, art and authentic indigenous food, the event runs from 3 to 11 p.m. Sept. 4; 10 a.m. to 11 p.m. Sept. 5 and 6; and 10 a.m. to 6 p.m. Sept. 7. Tickets are $20 per person per day and the powwow grounds are located at 100 Montauk Highway in Southampton.
2. Celebrate creativity in WHB Set for the Great Lawn (35 Main St.) in downtown Westhampton Beach, the annual outdoor Festival of the Arts is on Sept. 5 and 6 and features original work by artisans from across the country. Admission is free and the fest runs from 10 a.m. to 6 p.m. the first day and 11 a.m. to 6 p.m. the second.
3. See a classic street fair The San Gennaro Feast of the Hamptons comes to Good Ground Road in Hampton Bays Sept. 12 and 13, bringing the masses the best in Italian food and festive street fair fun. There’ll also be a fireworks display and free live concert featuring music from Foreign Journey. Visit sangennarofeastofthehamptons.com for more.
4. Whale Ho! The annual HarborFest comes to Sag Harbor Sept. 19 and 20, providing locals and visitors alike with end-of-summer fun that celebrates and honors the former whaling village’s rich nautical history from 9 to 6 p.m. both days. The action typically includes myriad local food vendors, an arts and crafts fair, whaleboat races, corn-shucking contests, fun and games for the kids, live music and much more. Visit sagharborchamber.com for the full lineup.
5. Shellin’ out in Montauk The Montauk Seafood Festival is on Sept. 12 and 13 and takes place on the village green in the center of town. Visitors will enjoy brews from Montauk Brewing Co., signature seafood dishes from about a dozen local vendors, plus live music and family-friendly activities, all of which help support the Montauk Friends of Erin and the East Hampton Kiwanis Club.
6. Rock out in Sag Harbor The annual Sag Harbor American Music Festival is from Sept. 24 through 27 and features free outdoor shows, three main stages and one ticketed headliner. The village is the venue, so expect dozens of live concerts popping up at some of your favorite Harbor haunts all weekend long.
7. Abstract, expressed at The Parrish A new exhibition, “Abstract Expressionism: The East End, 1940 to Today” begins at the Parrish Art Museum (279 Montauk Highway, Water Mill) Sept. 27 and continues through Valentine’s Day 2027. Set to explore the artistic innovation and cultural exchange found by artists living and working on the East End, the exhibition showcases pieces from the Abstract Expressionism movement and features works by Mary Abbot, James Brooks, Elaine de Kooning, Lee Krasner and Esteban Vicente.
8. Hamptons International Film Fest The 34th annual Hamptons International Film Festival takes place from Oct. 2-12 and features screenings, panel discussions and special events that celebrate the bold new voices of cinema across several venues throughout the Hamptons. Visit hamptonsfilmfest.org for details.
9. Haunted Walking Tour Step into the shadows of Sag Harbor on Oct. 17 with a haunted walking tour let by Annette Hinkle, board member at the Sag Harbor Whaling Museum. The tour will include stops in front of various homes and businesses, where a tapestry of firsthand ghost stories will be told. Starts at 5:30 p.m. at the Whaling Museum (200 Main St.).
10. Spooky disco In honor of Halloween, Guild Hall in East Hampton (158 Main St.) will host a silent disco on Oct. 30 from 7 to 10 p.m. featuring three DJs playing the best tunes from a slew of musical genres. Glowing headphones will be provided, costumes are encouraged, cocktails will be available and good vibes are required. Tickets are $25 per person; snag yours at guildhall.org.
