By Lauren Willett
August 20
Sunset Reception With Hamptons Polo House
Celebrate the new partnership between The Baker House 1650 and Hamptons Polo House at this invitation-only golden-hour gathering featuring cocktails, conversation and sustainable lifestyle vendors curated by PAZ Lifestyle. The Baker House 1650, 181 Main St., East Hampton; bakerhouse1650.com
August 22
Box Art Auction
Bid on one-of-a-kind works by East End artists at this annual benefit supporting East End Hospice. The evening features both a silent and a live auction, along with wine and hors d’oeuvres, with proceeds helping provide compassionate care throughout the community. Tickets from $100. St. Luke’s Episcopal Church Hoie Hall, 18 James Lane, East Hampton; eeh.org
Southampton Arts Center SummerFest
An evening of dining and live music on the grounds of the Southampton Arts Center supports its year-round arts programming. The annual gala will honor philanthropists John Paulson and Alina de Almeida with the 2026 Champions of the Arts Award. Tickets from $1,250. Southampton Arts Center, 25 Jobs Lane, Southampton; southamptonartscenter.org
G.E. Smith’s Portraits Featuring Patty Smyth & John McEnroe
Legendary guitarist G.E. Smith welcomes Grammy-nominated rocker Patty Smyth and special guest John McEnroe for songs and behind-the-scenes stories from their remarkable careers. Tickets from $196. The Hilarie and Mitchell Morgan Theater, Guild Hall, 158 Main St., East Hampton; guildhall.org
August 23
Gipsy Kings & Tonino Baliardo at The Room at The Clubhouse
Experience an intimate evening of live flamenco with the Gipsy Kings featuring Tonino Baliardo. Tickets from $241. The Room Hamptons, 174 Daniels Hole Road, East Hampton; clubhousehamptons.com
August 23–30
Hampton Classic Horse Show
One of the Hamptons’ signature summer traditions returns with a world-class show-jumping competition featuring Olympic medalists, national champion hunters and amateur riders from around the globe. Nearly 1,500 horses converge to participate in approximately 200 competitions. Daily admission $25 per carload for parking. Snake Hollow Road, Bridgehampton; hamptonclassic.com
August 29-30
East Hampton Art Affair
Browse original works by juried artists from across the country at this outdoor fine art fair in the heart of East Hampton. Set in Herrick Park, the free event showcases painting, sculpture, photography, jewelry, ceramics and more. Herrick Park, 67 Newtown Lane, East Hampton; artfestival.com
September 5
Hamptons Jazz Fest: The Meg Okura Quintet
Salute the close of the Hamptons Jazz Fest with the Meg Okura Quintet featuring saxophonist Sam Newsome. The Grammy-nominated violinist and composer brings her blend of jazz, classical and global influences to the stage for an unforgettable evening. General tickets $35, Member tickets $30, and Student/Youth tickets $20. 48 Madison St., Sag Harbor; thechurchsagharbor.org
September 19
The Bridge Car Show
This invitation-only exhibition celebrates the legacy of the original Bridgehampton Race Circuit with more than 300 exceptional postwar sports and competition cars. The Bridge, Bridgehampton; thebridgehamptons.com
September 20
The Bridge at Topping Rose House
Enjoy brunch by Jean-Georges alongside a display of rare classic automobiles celebrating Bridgehampton’s road-racing heritage. Live jazz and cocktails complete the experience, with proceeds benefiting Heart of the Hamptons. Tickets $275. Topping Rose House, 1 Bridgehampton-Sag Harbor Tpke., Bridgehampton; thebridgehamptons.com
September 27
Robby Hoffman at Guild Hall
A night of bold, unfiltered comedy with the Emmy-nominated comedian. Fresh off her acclaimed Netflix special Wake Up and her breakout role on HBO’s Hacks, Robby Hoffman brings her wildly original perspective to the stage. The Hilarie and Mitchell Morgan Theater, Guild Hall, 158 Main St., East Hampton; guildhall.org