1. THE FIGAWI RACE KICKS OFF THE SEASON WITH THRILLING COMPETITION AND ISLAND FESTIVITIES

MAY 26-29

The iconic Figawi sailing race is a weekend of intense competition and teamwork on the water. Sailors from all over the East Coast gather to race from Hyannis to Nantucket, marking the unofficial start of the summer season. Enjoy the thrill of the race and join the festivities as the island welcomes the sailors ashore. For more information, visit figawi.com.

2. EXPLORE THE MAGIC OF THE NANTUCKET BOOK FESTIVAL

JUNE 15-18

A call to all book lovers and literary enthusiasts! There is no better way to celebrate literature than by attending the Nantucket Book Festival, which fosters dialogue between authors and readers. The festival features author talks, panel discussions and book signings, allowing you to meet your favorite writers and discover new ones. For more information, visit nantucketbookfestival.org.

3. FAIRWINDS’ BLOOMING BIDS AIMS FOR A GREENER FUTURE

JUNE 22 12-7 PM

Bartlett’s Farm Garden Center

Support Nantucket’s Fairwinds Counseling Center by participating in its annual Blooming Bids event. This unique fundraiser features a silent auction with great items to bid on, like art, experiences and gift certificates. Don’t miss this delightful evening that will benefit a vital community resource. For more information and to purchase tickets, visit cbo.io/bidapp/index.php?slug=fairwinds.

4. THE 28TH ANNUAL NANTUCKET FILM FESTIVAL

JUNE 21-26

Lights, camera, action! The Nantucket Film Festival showcases the best in independent cinema while fostering an appreciation for the art of screenwriting. The event includes film screenings, panel discussions and workshops with industry insiders. Don’t miss the chance to discover your next favorite movie. For more information and to purchase a pass, visit nantucketfilmfestival.org.

5. ANDY FRASCO AND THE U.N. BRING THE HEAT TO THE CHICKEN BOX

JUNE 18 — 9 PM

The Chicken Box

Get ready to dance the night away with Andy Frasco and his high-energy band, The U.N. This dynamic live performance at The Chicken Box promises a night of unforgettable music and entertainment. Frasco’s electrifying stage presence and soulful tunes will have you grooving all night long. For more information and to purchase tickets, visit thechickenbox.com/andy-frasco-the-u-n/.

6. HILARIOUS ADVENTURE WITH BOEING BOEING

JUNE 7-24

Bennett Hall

Experience the magic of live theater with a production of the classic play Boeing Boeing. This hilarious play takes you on a whirlwind adventure full of mistaken identities, romance and non-stop laughter. For more information and to purchase tickets, visit nantucketculturaldistrict.org/event/boeing-boeing/.

7. CELEBRATE NANTUCKET’S MARITIME LEGACY AT SANKATY HEAD LIGHTHOUSE—OPENING DAY

JUNE 17 10 AM-3 PM

Sankaty Head Light

Embark on a journey through Nantucket’s maritime history by attending opening day of one of the island’s iconic lighthouses. This annual event provides a rare opportunity to explore the lighthouse and learn about its unique role in guiding ships throughout the years. For more information, visit sconsettrust.org/event/summer-lighthouse-open-day/.

8. NANTUCKET PRESERVATION MONTH CELEBRATES THE ISLAND’S RICH ARCHITECTURAL HERITAGE

JUNE

Nantucket Preservation Month offers an array of events, tours and workshops throughout June that showcase the island’s unique architecture and historic preservation efforts. From exploring centuries-old homes to learning about the skilled artisans who have preserved these structures, this month-long celebration provides an engaging experience for history fanatics and architecture enthusiasts. For more information, visit www.nantucketpreservation.org/may-is-preservation-month-950/.

9. SAM SYLVIA GOLF TOURNAMENT SUPPORTS NANTUCKET'S YOUTH

JUNE 4-5

Sankaty Head Golf Club

The Sam Sylvia Golf Tournament is a thrilling two-day competition. Hosted at the picturesque Nantucket Golf Club, the tournament raises much-needed funds for the Nantucket Boys and Girls Club, a nonprofit organization dedicated to providing programs and services for the island’s youth. For more information and to donate, visit nantucketboysandgirlsclub.org.

10. DREAMCATCHER EVENT SUPPORTS PASCON’S COMPASSIONATE CARE AND SERVICES

JUNE 11

White Elephant Ballroom

The Dreamcatcher event is an evening of fine dining, live entertainment and philanthropy set in a stunning Nantucket venue. The event highlights PASCON’s unwavering commitment to offering compassionate care and support to those in need, with proceeds benefiting its programs and services. For more information and to purchase tickets, visit pascon.org/events/dreamcatcher-dinner-and-auction/.