Auction Logo

Saturday, November 22, 6pm

Doubletree Hotel |

11 Beaver Street  | Milford, MA

A showcase of the area 's favorite restaurants wine beer liquor tasting and music

Yacht rock music
with Loaded dice

A group of six people smiling at a table, seated at an event. They are surrounded by decorations and food.

Auction, dinner & Dance
the night away

Join us for a night of dinner, dancing, auction and a whole lotta fun!

Auctions Aweigh! This year’s event sets sail for an unforgettable evening filled with music, laughter, and good vibes on the high seas.

Picture this: Local band “Loaded Dice” rocking the deck, a feast fit for the captain’s table, and an auction loaded with treasures just waiting to be discovered—perfect for holiday gifting or treating yourself. Add in games, raffles, and a fully stocked cash bar, and you’ve got the makings of a night to remember. Don’t miss your chance to climb aboard this one-of-a-kind voyage, all while supporting the Tri-County Regional Chamber. Tickets are going fast, so grab yours before this ship sails without you!


** Dress attire is cruise themed. Go all out or keep it casual—just have fun with it! **

Ways to Participate

Live Music by Loaded Dice – Your Yacht Rock Soundtrack for the Night

No night on the high seas is complete without the perfect music—and Loaded Dice is ready to deliver the ultimate yacht rock experience!

The first half of the evening sets the mood with smooth, laid-back classics - perfect for mingling, enjoying dinner, and browsing the auction tables. Once the auction wraps, the energy kicks up and the dance floor comes alive! Get ready to sing and groove to upbeat yacht rock favorites.

Loaded Dice will keep the good vibes flowing all night long, delivering the ultimate smooth-meets-funky soundtrack for

Anchors Aweigh: A Night on the High Seas.


"Cruise for 2 or CASH for you" Raffle!

A banner that says dinner for 2 anywhere in the world

Win the Ultimate Getaway – A Cruise for Two or $5,000 Cash!


Ready to set sail on the vacation of your dreams? Here’s your chance! For just $30 a ticket, you could win a luxury cruise for two to the destination of your choice (up to $5,000 value) – or take the cash instead and plan your own adventure!


Only 500 tickets will be sold, making your odds better than most raffles out there. The winning ticket will be drawn at our "Auctions Aweigh" Fundraiser on Saturday, November 22nd – but you don’t need to be present to win.


Don’t miss your shot at the getaway of a lifetime. Tickets are limited – grab yours today before they’re gone! Raffle tickets are on sale beginning August 1st, and winner will be drawn at the Auction Aweigh; A Night on the High Seas on Saturday, November 22rd. Cash or checks can be accepted for payment, and you can pick up your tickets at:


  • Tri-County Regional Chamber Office, 258 Main Street, Suite 306 | Milford, MA 01757
  • Bright Insurance Agency, 6 Congress Street, Milford, MA 01757


Click here for rules and regulations.

Congratulations to Cindy Katz, the lucky winner of our "Dinner for 2 Anywhere in the World" raffle at last year's event! Cindy was present at the auction and couldn't contain her excitement when her name was announced. Her winning ticket was #5—what a moment to remember!

Cindy Katz
Cindy & Jeff Katz