Winners Circle Sweepstakes Banner

All 1st place team members will receive a unique ID number to be entered into the Winner’s Circle Sweepstakes, presented by TripCaddie.

Two (2) individual Grand Prize winners will be selected to win a Golf Trip of a Lifetime. A 3 day, 2 night trip for each winner + 1 guest will include lodging and greens fees for three (3) 18-hole rounds at a destination of choice including Pinehurst Resort, Streamsong Resort, Kohler Resort, TPC Sawgrass & more.

Live drawing will take place on Tuesday, November 14th 2023 at 9:00 PM Eastern Time (Livestream).

Dozens of additional sweepstakes winners will win prizes including Callaway Golf golf equipment and gift cards. A unique identifier will be delivered to each 1st place team member at the conclusion of the season. Additional details included in this year’s Player’s Information Packet.

About TripCaddie

When planning your next buddy golf trip, make TripCaddie your first destination! Visit to get started!

TripCaddie makes offers tools and services that make planning a golf trip a SNAP!

TripCaddie features:

  • The all new Golf Trip Concierge service, a personalized trip planner to help you plan your golf trip!  Let TripCaddie do all the work
  • The Golf Trip Manager, a private website to help you organize and share all of your golf trip information with your buddies
  • The #1 Golf Travel PodcastThe Golf Trip Authority, to help your group show up to the golf trip prepared

A SPECIAL OFFER (Save $100): Through the 2023 season, TripCaddie is offering our TGA members $100 OFF your trip when booking a golf trip using the Golf Trip Concierge – Just tell them you are with Twilight Golf Association when you call!*  Also, members get a FREE UPGRADE to the Pro version of the Golf Trip Manager by using the promo code “TWILIGHT” at the payment checkout.  Terms and Conditions apply, visit for details.