There are TWO specialty raffles for the 2026 Wish Upon A Star gala!

1. Heroes retreat ($100/ticket)

This three-bedroom coastal retreat is designed for relaxation and fun. The heart of the home—the bright, airy main level—features a vaulted ceiling, big windows, and a comfy sectional (with a Tempur-Pedic sleeper!) for movie nights and lazy afternoons. The fully stocked kitchen has everything you need - stainless-steel pots and pans, wooden cooking utensils and cutting boards, and kid-friendly dishes (divided trays and silverware). Don’t forget to grab a snack for the pool on the BPA free outdoor dining items (bowls, cups, and plates)! So whether you're whipping up breakfast at the bar, gathering around the dining table, or enjoying a meal on the deck, it’s all easy and effortless.

A 3-to-7-day getaway in the off season (you pick the length of stay that works best for you, anytime between May 2nd and 16th) at the all-American Heroes Retreat 2!
This three bedroom, 2.1 bathroom beach house sleeps 10 and is nestled in the quaint North End area of this seaside beach town. Fully furnished, pool, hot tub, outdoor cabana area and just a 5 minute walk to the beach
Estimated Fair Market Value: $3,000
Learn more about the property here: https://www.siebert-realty.com/sandbridge/heroes-retreat-2/

2. OBX

Make unforgettable memories with the family at On Island Time—a vacation home designed with comfort, convenience, and togetherness in mind. Perfectly located just a short walk from the beach, shopping, and local restaurants, this home puts everything the entire family needs within easy reach. You'll love being just two blocks from a lifeguarded beach access and close to the brand-new Meekins Field park, which features a playground, swings, splash pad, tennis courts, and a soccer field—fun for all ages!

PLEASE NOTE: If you would like to pay for a ticket by check, please send a check, made out to Connect With A Wish, and send it c/o Wish Upon A Star Gala to 2492 N. Landing Rd., Ste. 102, Virginia Beach, VA 23456. The memo line of the check should read "CWW 2026 Gala Raffle"

Other terms: Tickets go on sale Saturday, February 7th. Both drawings will take place the evening of March 28, 2026, during the 2026 Wish Upon A Star Gala. You DO NOT need to be present at the gala to win, and someone from Connect With A Wish will contact you within 72 hours of the drawing if you are not present. For any questions, please contact Nicholas Waid, Office Manager, at 757-337-2657 or by email at officemanager@cwwvb.org.

Wish Upon A Star 2026 Raffles

By Connect With A Wish, Inc.

Wish Upon A Star 2026 Raffles

CWW 2026 SPECIALTY RAFFLES

Team Members