By Lauren Willett
ASPEN
June 4
Rodney Crowell at Wheeler Opera House
An evening of soulful music with a live performance by troubadour Rodney Crowell at the Wheeler Opera House. Tickets from $28. Wheeler Opera House, 320 E. Hyman Ave., Aspen; wheeleroperahouse.com
June 6
Megan O’Grady: How It Feels to Be Alive
A discussion between Daniel Merritt and author Megan O’Grady on her new book, How It Feels to Be Alive: Encounters With Art and Our Selves, in which she talks about how creativity helps us find clarity in an uncertain world. Explore Books, 221 E. Main St., Aspen; explorebooks.org
June 19–21
Aspen Food & Wine Classic
The season’s most anticipated culinary gathering returns—it’s where top chefs, winemakers and tastemakers come together for a weekend of positive vibes, good people and great flavors. Passes from $2,950. classic.foodandwine.com
June 20
Tommy Emmanuel at Wheeler Opera House
Australian guitar virtuoso Tommy Emmanuel brings his dynamic sound to the Wheeler Opera House. Tickets from $40. Wheeler Opera House, 320 E. Hyman Ave., Aspen; wheeleroperahouse.com
July 13
19th Annual Quality of Life Cancer Fund Event
A heartfelt gathering in Roaring Fork Valley honoring community strength and supporting meaningful initiatives in cancer wellness. Berger Residence, 314 W. Gillespie St., Aspen; aspenchamber.org
June 25
TACAW Gala 2026
An artful celebration of creativity and community, this gala brings together culture, conversation and support for the arts amid Aspen’s vibrant summer backdrop. Tickets $500 per person. tacaw.org
July 27–31
Air Aspen
Explore the role of art in addressing the complexities of life through collaborations, conversations and site-specific creations and performances. airaspen.org
July 28–August 1
Intersect Aspen Art and Design Fair
An intimate evening for visitors to experience modern and contemporary art and design presented by top galleries from around the world. Aspen Ice Garden, 233 W. Hyman Ave., Aspen; http://www.intersectaspen.com
September 22–27
Aspen Film Fest
An annual cinematic celebration of films curated to explore the human condition through diverse lenses. 110 E. Hallam St., Suite 115, Aspen; aspenfilm.org
Hamptons
May 3–July 19
Claire Watson: Re-Paired
A meditation on presence and the human form, Re-Paired invites viewers into Claire Watson’s visual dialogue through sculptures of deconstructed leather garments. Tickets $12 for adults, $10 for seniors, and free for kids and students; 158 Main St., East Hampton; guildhall.org
May 23
The Story of America: 1776-2026, Exhibition Opening Reception
This exhibition, which runs until July 18, brings 250 years of American presidential campaign history to life with objects from the Museum of Democracy’s Wright Family Collection. 25 Jobs Lane, Southampton; southamptonartscenter.org
May 30
35th Annual Decorators-Designers-Dealers Sale and Auction Benefit Gala
This fabulous annual sale features designer furniture, rare antiques, decorative accessories and much more, in support of the Southampton Fresh Air Home, serving youth with physical disabilities. sfah.org
June 5
Hamptons Polo Club: Independence Cup 8 Goal Begins
A social event ushering in the polo season that’s best enjoyed with a glass in hand and eyes on the field. 206 Millstone Road, Water Mill; hamptonspoloclub.com
June 6
All Against Abuse Gala
Join The Retreat for an elegant evening of cocktails, hors d’oeuvres, and inspiring stories of hope and healing. Proceeds support lifesaving services for survivors of domestic abuse, sexual assault and human trafficking. Tickets from $750. 25 Jobs Lane, Southampton; secure.qgiv.com
June 8
Art Social: Watercolor—Seashell, Feather, & More
A guided watercolor painting session in the Guild Hall garden; all levels of art experience are welcome. Tickets $57. 158 Main St., East Hampton; guildhall.org
Forget-Me-Not Gala
At CaringKind’s 30th anniversary gala, hosted by David Hyde Pierce, support and celebrate the organization’s Connect2Living initiative, designed to help people living with Alzheimer’s disease or dementia and their families live well. Tickets from $1,250. Cipriani 42nd St., 110 E. 42nd St., Manhattan; ckgala.org
June 12 and 13
CRUCE DE CAMINOS / CROSSROADS: A NIGHT OF SHORT PLAYS
An evening of multilingual short plays led by 2026 Guild Hall Community Artists-in-Residence Margarita Espada and Minerva Perez. Tickets $18. 158 Main St., East Hampton; guildhall.org
June 20
En Plein Air With Howard Rose
An open-air painting class led by Howard Rose that invites artists of all levels to develop their skills on-site at the Southampton Arts Center. Tickets $20. 25 Jobs Lane, East Hampton; southamptonartscenter.org
Hamptons Pride Party
A celebration of love at LongHouse Reserve for Hamptons Pride’s annual Pride Party fundraiser. Tickets from $189. 133 Hands Creek Road, East Hampton; hamptonspride.org
June 27
Palm Tree Music Festival Hamptons
The coastal music festival brings together world-class DJs for a sun-drenched, high-energy event you won’t want to miss. Tickets from $349. The Shinnecock Nation, Southampton; posh.vip
Unlimited Earth Care
In celebration of Unlimited Earth Care headquarters’ 20 years in Bridgehampton, interior designer Bea Pernia will unveil a curated selection of pieces from her latest sensorial Bubble collection. 2249 Scuttle Hole Road, Bridgehampton; unlimitedearthcare.com
Whimsy Latin Jazz Dance Party
Kick off the summer season and support the Southampton Arts Center’s mission to build community through the arts. Tickets from $200. 25 Jobs Lane, Southampton; southamptonartscenter.org
Beautopia Summer Benefit
An annual art auction held in the spectacular gardens of LongHouse Reserve, where handcrafted cocktails are sipped and live music plays as the sun sets. Tickets from $200. 133 Hands Creek Road, East Hampton; secure.qgiv.com
June 28
Parrish Art Museum Opening Reception
Get an early look at new exhibitions and experiences that Parrish Art Museum brings to the community this year. 279 Montauk Hwy., Water Mill; parrishart.org