Top Hamptons Events Oct. 22-26, 2026: Live Music, Art, Theater, Fall Festivals and More

From Southampton to Montauk, the East End’s weekend calendar offers live performances, art, film, fall celebrations and some distinctly Hamptons traditions.

The final full weekend of October brings a Rock & Roll Hall of Famer to Riverhead, a celebration of sculpture in Sag Harbor, theater in Southampton and independent film in Montauk. There are also fall festivals, family activities and a few Halloween traditions. Here are Spark Hamptons’ picks for Oct. 22-26.

EDITOR’S TOP 5 PICKS

1. Sag Harbor Ragamuffin Parade & Carnival — Sag Harbor, Oct. 25

2. Booker T. Jones at The Suffolk — Riverhead, Oct. 25

3. Disco Ball Benefiting Our Fabulous Variety Show — East Hampton, Oct. 24

4. Art in the Garden: J. Oscar Molina at Julie Keyes Art — Sag Harbor, Oct. 24

5. Wölffer Cider Fest — Sagaponack, Oct. 24

MUSIC & ENTERTAINMENT

Booker T. Jones at The Suffolk
Sunday, Oct. 25, 7 p.m. | $45-$89
The Suffolk, 118 E. Main St., Riverhead

Rock & Roll Hall of Fame inductee Booker T. Jones brings his legendary soul sound to Riverhead. The leader of Booker T. & the M.G.’s and a driving force behind Stax Records performs classics including “Green Onions” and “Time Is Tight,” along with music and stories from a career that includes collaborations with Otis Redding, Wilson Pickett and Bob Dylan.

Nancy Atlas at Stephen Talkhouse
Thursday, Oct. 22, 8 p.m. | $40
Stephen Talkhouse, 161 Main St., Amagansett

East End favorite Nancy Atlas returns to the Talkhouse with her blend of rock, blues and roots music. A longtime fixture of the Hamptons music scene, Atlas brings her powerhouse vocals and energetic stage presence to one of the area’s best-known live music venues.

Youth Open Mic Night at Hampton Coffee Company
Friday, Oct. 23, 6 p.m. | Free
Hampton Coffee Company, Hampton Bays

Young performers in grades 5-12 are invited to take the microphone for an evening of music, poetry, comedy and other creative performances. A chance for local students to share their talents in a welcoming community setting.

ART & CULTURE

Art in the Garden: J. Oscar Molina at Julie Keyes Art
Saturday, Oct. 24, 2 p.m.
Julie Keyes Art, 45 Main St., Sag Harbor

Currently representing El Salvador at the Venice Biennale, sculptor J. Oscar Molina is the featured artist at a reception in the newly reimagined garden at Julie Keyes Art. His evocative Children of the World sculptures explore migration, displacement, resilience and the search for belonging. Molina’s work is also featured in El Salvador’s inaugural national pavilion at this year’s Biennale.

Artists’ Table at The Watermill Center
Saturday, Oct. 24, noon | Reservations required; admission through venue
The Watermill Center, 39 Water Mill Towd Road, Water Mill

The Watermill Center’s Artists’ Table series brings together art, conversation and a locally sourced meal. Curator Marcelo Gabriel Yáñez and photographer Matthew Leifheit discuss The Disappearance of Landscape: Oakleyville, followed by lunch prepared by chef David Chaffin.

Stories & Songs: Betsy Sussler With Real East End Brass
Friday, Oct. 23, 6 p.m.
The Church, 48 Madison St., Sag Harbor

Betsy Sussler, founding editor of BOMB magazine, discusses her debut novel, Station of the Birds, in conversation with The Church’s April Gornik. The evening also features live music by Real East End Brass, bringing together literature, conversation and performance. BookHampton participates in the program.

Curator-Led Tour: Abstract Expressionism — The East End, 1940 to Today
Friday, Oct. 23, 3 p.m. | $30 adults; discounts and free admission for eligible visitors
Parrish Art Museum, 279 Montauk Highway, Water Mill

Associate curator Kaitlin Halloran leads a tour exploring the East End’s role in Abstract Expressionism, from Jackson Pollock and Lee Krasner’s arrival in Springs in 1945 to contemporary artists. The exhibition traces the region’s influence on one of America’s defining art movements. Advance registration recommended.

In-Process: J. Bouey Dance Projects — The Living Ancestors
Saturday, Oct. 24, 7 p.m. | Tickets through venue
Guild Hall, 158 Main St., East Hampton

Contemporary dance company J. Bouey Dance Projects shares excerpts from The Living Ancestors, a multimedia dance-theater work in development described as a disco-funk space opera. The presentation offers audiences a look at the creative process, followed by a conversation with the artists.

FILM & THEATER

Offshore Art & Film Festival
Thursday-Saturday, Oct. 22-24 | Tickets vary by program
Montauk Yacht Club and Montauk Playhouse Community Center, Montauk

The fifth annual Offshore Art & Film Festival brings independent filmmakers, artists and live music to Montauk for three days of screenings and conversations. Friday’s program at the Montauk Yacht Club features short films and a filmmaker Q&A. Saturday’s Surf & Skate Night at the Montauk Playhouse celebrates surf, skate and coastal culture.

The Great Gatsby: A Live Radio Play
Friday, Oct. 23, 7 p.m.; Saturday, Oct. 24, 2 and 7 p.m.; Sunday, Oct. 25, 2 p.m. | $25; $20 for members
Southampton Arts Center, 25 Jobs Lane, Southampton

Center Stage presents F. Scott Fitzgerald’s The Great Gatsby as a live radio play, with an ensemble bringing more than two dozen characters to life. The production revisits the glamour, ambition and tragedy of the Jazz Age through the format of a theatrical radio broadcast.

Hamptons Pride Film Series: Twinless
Sunday, Oct. 25, 4 p.m. | Tickets through theater
Bay Street Theater, 1 Long Wharf, Sag Harbor

The Hamptons Pride Film Series presents Twinless, the Sundance Audience Award-winning drama written and directed by James Sweeney. Dylan O’Brien stars as a young man grieving his twin brother who forms an unexpected friendship at a support group. Sweeney and Aisling Franciosi also star.

FALL FESTIVALS & FAMILY FUN

Autumn Festival at Bridge Gardens
Saturday, Oct. 24, noon | Free; donations appreciated
Bridge Gardens, 36 Mitchell Lane, Bridgehampton

The Peconic Land Trust hosts an afternoon of seasonal activities, including pumpkin painting, a scavenger hunt, crafts and refreshments. Costumes are encouraged, and families can enjoy the fall setting of Bridge Gardens. Reservations requested; rain or shine.

Wölffer Cider Fest
Saturday, Oct. 24, 2 p.m. | Pay as you go
The Wine Stand at Wölffer Estate, 3312 Montauk Highway, Sagaponack

Wölffer celebrates the fall harvest with its No. 139 ciders, live music, outdoor games, a bouncy house and food from the LUNCH Lobster Roll truck. All ages are welcome. Food and beverages are purchased separately. Reservations are available, and walk-ins are welcome.

Guild Hall Family Day
Saturday, Oct. 24, 1 p.m. | Free
Guild Hall, 158 Main St., East Hampton

Guild Hall welcomes families for an afternoon of creative activities, including an oil pastel workshop led by Kayla Matters and self-guided projects inspired by the exhibitions.

HALLOWEEN HIGHLIGHTS

Sag Harbor Ragamuffin Parade & Carnival
Sunday, Oct. 25, 12:45 p.m. parade lineup; 1:30 p.m. carnival | Free parade
Nassau Street and Main Street, Sag Harbor; carnival at Sag Harbor Whaling & Historical Museum, 200 Main St.

One of Sag Harbor’s favorite Halloween traditions brings costumed children, adults and pets through the village. Participants line up on Nassau Street at 12:45 p.m. and parade along Main Street to the Whaling Museum. A carnival hosted by Bridgehampton School’s Drama Club follows, with games, activities and music on the museum lawn.

Witches Paddle on Three Mile Harbor
Saturday, Oct. 24, 3:30 p.m. | $20-$35
Paddle Diva, 10 Boatyard Road, East Hampton

Witches trade broomsticks for paddleboards at the second annual Witches Paddle, organized by the Surfrider Foundation’s Eastern Long Island Chapter with Paddle Diva and community partners. Participants dress in witch-inspired costumes and take to Three Mile Harbor while raising money to protect clean water and the East End’s coastlines.

Little Lucy’s Annual Halloween Pet Parade
Saturday, Oct. 24, 1 p.m. | $20 per dog, cash
Agawam Park, 51 Pond Lane, Southampton

Southampton’s canine costume parade returns with dressed-up dogs, live music, vendors, judges, raffles and costume awards. Adoptable dogs will also be on hand. Proceeds benefit the Suffolk SPCA and Southampton Animal Shelter. Registration begins at 1 p.m. For information, call 631-287-2352.

* For additional costume parties, haunted attractions and family celebrations, see Spark Hamptons’ separate Halloween guide for the Hamptons,  and the North Fork Halloween Guide.

BENEFITS & COMMUNITY EVENTS

Disco Ball Benefiting Our Fabulous Variety Show
Saturday, Oct. 24, 6:30 p.m. | Tickets from $107 adults; $55 students; VIP packages available
Frankie’s Fabulous Italiano, 44 Three Mile Harbor Road, East Hampton

Get out the disco attire for an evening of dancing, music, food, drinks, raffles and auctions supporting Our Fabulous Variety Show’s mission to make performing arts accessible to the community. This year’s honorees include Scott Benaglio, Devon Leaver, tap dancer and choreographer Leonardo Sandoval and WLIW radio host Gianna Volpe. A VIP cocktail reception precedes the main event.

LVIS 33rd Annual Landmarks Luncheon
Saturday, Oct. 24, 11:30 a.m. | $150
Maidstone Club, 50 Old Beach Lane, East Hampton

Architectural conservator and former New York City Landmarks Preservation Commissioner Michael Devonshire presents “The Good Fight: Why We Preserve Our Heritage,” exploring the cultural, environmental and economic benefits of historic preservation. His lecture will be followed by lunch at the oceanfront Maidstone Club. Proceeds support local preservation projects through the Ladies’ Village Improvement Society.

Angela LaGreca

Editor, Co-Founder/Publisher

Angela LaGreca, Editor-in-chief and co-Founder/Publisher of Spark Hamptons, is a four-time Emmy Award-winning journalist, producer, writer and comedian/host. Her TV credits include NBC’s “Today,” ABC’s “The View,” and, most recently, the primetime cable news program “Cuomo” on NewsNation. On the East End, she was the Creative Director at LTV, VP Features/Events/Photo Editor at Dan’s Papers, and has performed at Guild Hall, Bay Street Theater and the WHBPAC. Her publishing career began at Modern Photography, where she was managing editor. LaGreca lives in Manhattan and East Hampton and can be reached at angelatvmedia@gmail.com and angela@sparkhamptons.com .