This captivating 24”x36” oil on canvas, titled “Late Afternoon Twilight,” is a deeply personal and evocative work by beloved Vineyard artist Allen Whiting. Known for his impressionistic landscapes and intimate connection to the Island, Whiting created this piece especially for the HPCMV 2025 Summer Soirée, offering collectors a rare opportunity to acquire a one-of-a-kind original. Based on a 9”x12” plein air study painted outdoors during the warmer months, Late Afternoon Twilight was developed in Whiting’s studio over the winter. It depicts sheep grazing peacefully on Whiting Farm in West Tisbury, bathed in the golden light of his favorite season, autumn. As Whiting enters his 80th year and sixth decade of landscape painting, this piece reflects both his mastery of light and place and his enduring connection to the land.

Donor: Allen Whiting

Grab three friends and join writer, fisherman, and storyteller Nelson Sigelman for a memorable low-tide adventure on the shores of Lagoon Pond or Lake Tashmoo. Together, you'll rake up a half-bushel of hard-shell clams from Vineyard waters under Nelson’s expert guidance. To get in the spirit, you’ll receive a personalized copy of Nelson’s book, Martha's Vineyard Fish Tales: How to Catch Fish, Rake Clams, and Jig Squid, with Entertaining Tales About the Sometimes Crazy Pursuit of Fish. Then pick up your very own clam rake with a $25 gift card to Dick’s Bait & Tackle in Oak Bluffs. After the fun, you’ll have earned your feast: a full clambake for ten, delivered to your door by Fella’s Catering—complete with chowder, lobsters, steamers, mussels, and more.

Donors: Nelson Sigelman, Dick’s Bait & Tackle, and Fella’s Catering

Escape to the U.S. Virgin Islands with a three-night stay at Lovango Resort & Beach Club, a private island retreat from Mark and Gwenn Snider, owners of the Winnetu and the Nantucket Hotel. Stay in a luxurious ocean-view glamping tent with a king bed, full bath, and daily continental breakfast. Enjoy beach club membership, round-trip ferry service to St. John and St. Thomas, and relax in style with a 100% cotton beach blanket and premium sunscreen from The Green Room. A handmade mini tote by M-C Lamarre from Basketcase MV adds the perfect finishing touch to your tropical getaway. To make your trip even more carefree, a $500 Visa gift card—generously provided by the HPCMV Board of Directors—is included to help cover travel expenses or vacation indulgences.

Donors: Mark & Gwenn Snider/Lovango Resort & Beach Club, The Green Room, Basketcase MV, and HPCMV Board of Directors

Calling all Sox fans—this one’s for you! Kick off your baseball adventure with two round-trip tickets on Cape Air, flying from Martha’s Vineyard to Boston. Your day at Fenway Park begins with a behind-the-scenes tour of the historic ballpark before settling into infield box seats to cheer on the Red Sox, courtesy of Moxie and David Ginsberg/Red Sox. After the game, head across the river to The Charles Hotel in vibrant Harvard Square, where you’ll enjoy a one-night stay in a deluxe room, generously provided by Richard Friedman. Can’t get enough baseball? When the season winds down, use your two tickets to Red Sox Spring Training at JetBlue Park in Fort Myers, Florida. While you’re in sunny SWFL, enjoy either a relaxing round of golf at The Colony Golf & Country Club or a half day of fishing with Steve & Liza May on Estero Bay, Pine Island Sound, and/or the Gulf of Mexico.

Donors: Cape Air, Moxie & David Ginsberg/Red Sox, Richard Friedman/The Charles Hotel, and Liza & Steve May

Step aboard the Magic Carpet, a stunning 56-foot Sparkman & Stephens classic wooden sailboat, for an unforgettable two-hour sunset sail for up to 14 people through the sparkling waters of Vineyard Sound. This elegant maritime experience is helmed by Captains Lee Taylor and Todd Bassett of Island Classic Charters, whose expert seamanship and love of the ocean promise a truly memorable journey. Sit back, relax, and take in the beauty of the Island coastline as the sun dips below the horizon—an evening of classic sailing, breathtaking views, and timeless Vineyard magic. The auction package includes a gift basket of goodies from Soigne to enjoy during your sail. You’ll also receive a handmade nautical rope basket by M-C Lamarre of Basketcase MV—perfect for toting your favorite beverages—along with a $50 gift certificate to Al’s Package Store to fill it up.

Donors: Island Classic Charters/Magic Carpet, Lee Taylor, Todd Bassett, Soigne, Basketcase MV, Al’s Package Store

Enjoy a luxurious 2-night stay at Pier House Resort and Spa in vibrant Key West, featuring stunning ocean views, spa amenities, and multiple dining options. Relax on the beach, indulge in spa treatments, or savor sunset cocktails—plus, receive a $100 gift certificate to Rags for something special to pack and a $100 gift card to Caleen’s Day Spa toward a mani-pedi or spa treatment of your choice to prepare for your trip! While in Key West, enjoy a night out with two tickets to a production at the acclaimed Waterfront Playhouse, the island’s premier professional theater. To make your getaway even more seamless, this package also includes a $200 Visa gift card, donated by the HPCMV Board of Directors to help with travel or vacation extras.

Donors: Pier House Resort and Spa, Waterfront Playhouse, Rags, Caleen’s Day Spa, and HPCMV Board of Directors

Treat yourself and three lucky guests to an unforgettable night with four premium tickets to see the legendary James Taylor live at the iconic MGM Music Hall at Fenway in Boston on Tuesday, August 26th, 2025. Experience timeless melodies and soulful storytelling in an intimate setting, all while enjoying the ease of round-trip car service from Cape Cod to Boston. After the concert, unwind with a comfortable overnight stay at a stylish Boston hotel—you'll receive two $500 gift cards to Hotel Commonwealth. This is your chance to indulge in a seamless, star-studded evening filled with great music, effortless travel, and cozy accommodations—the perfect escape for music lovers and adventure seekers alike.

Donors: Anonymous

Restrictions: Concert tickets are non-exchangeable. Car Service is valid only on August 26 & 27, 2025.

Step into Vineyard elegance with a private cocktail party for you and 17 guests at the iconic Vose Boathouse, generously offered by The Vose Family Trust, a 122-year-old waterfront gem with sweeping views of Edgartown Harbor, the town skyline, and the lighthouse beyond. This one-of-a-kind setting offers the perfect backdrop for a memorable celebration—be it a birthday, anniversary, or summer gathering with friends. Your evening will be graciously hosted by a member of the Vose family and features scrumptious hors d’oeuvres by Theresa Manning of Quitsa Cuisine—a delicious complement to this intimate, harborfront experience. To elevate the experience, you’ll also receive six bottles of wine for your event, courtesy of Jim’s Package Store.

Donors: The Vose Family Trust, Quitsa Cuisine, Jim’s Package Store

Restrictions:Boathouse is available on a mutually agreed upon date to be used by October 15, 2026, party with set-up and clean-up from 4:30 p.m. to 7:30 p.m. (negotiable). Mutually agreed upon date for Quitsa Cuisine.

Treat yourself and a few close friends to an intimate two-hour live music experience right in the comfort of your home, featuring the phenomenal Delanie Pickering and Jeremy Berlin. Let the incredible talents and masterful musicianship of this dynamic duo create an evening to remember. Don't miss this unique opportunity to bring two of the Vineyard’s best straight to your living room! This evening is perfectly paired with delectable lite bites from S&S Kitchenette and a curated assortment of Yommi MV Bars, the Island’s favorite feel-good treat. A stylish soirée where irresistible flavors meet unforgettable rhythms.

Donors: Delanie Pickering, Jeremy Berlin, S&S Kitchenette, and Yommi MV