Winners Circle Sweepstakes Banner

All 1st place team members during the 2024 season will receive one entry 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 12th 2024 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.

2023 Grand Prize Winners:

Frank V. | Howell Park Golf Course (NJ)         Nick B. | Riverwalk Golf Club (CA)

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 #1 Golf Travel PodcastThe Golf Trip Authority, to help your group show up to the golf trip prepared
  • The all new Golf Trip Concierge service, a personalized trip planner to help you plan your golf trip. Let TripCaddie do all the work when you Request a Quote!
  • The Golf Trip Manager, a private website to help you organize and share all of your golf trip information with your buddies
  • A SPECIAL OFFER (Save $100): Through the 2024 season, TripCaddie is offering Twilight Golf members $100 OFF when booking a golf trip using the Golf Trip Concierge – just tell them you are with Twilight Golf when you call!
  • Also, members can plan their next golf trip with the Golf Trip Manager by TripCaddie for $1! Just use the promo code “TWILIGHT1” at the payment checkout when upgrading your trip. Terms and Conditions apply, visit for details.