This page highlights some of the events our club & members will attended throughout 2026.

Cadillac Night is Back at Bear Mountain!

Mark your calendars, Cadillac fans! The season is set, and the trophies are waiting.

• Dates: May 20, June 17, July 15, Aug 12, Sept 9
• Feature: Special Cadillac trophies sponsored by CPR (Cadillac Parts & Restoration).

Pro-Tips for a Smooth Cruise:

1. Stay Informed: Join the Bear Mountain Cruise Facebook Group for the latest on rain dates and event news.
2. Follow the Crew: With construction ongoing at the Inn, please be patient and follow staff directions for entry and parking.

Let’s fill the mountain with chrome! See you there. 

SAVE THE DATE: Icy Treats & Classic Seats!

Nothing says summer like a cruise to the Red Rooster! The NY-CT Two Rivers Region is heading to Brewster for a Summer Night Ice Cream Run.

• When: Thursday, July 16th, 2026
• Time: 6:00 PM – 8:30 PM
• Where: Red Rooster Drive-In, Brewster, NY

Dust off the chrome, drop the top, and join us for a great night of cars and conversation. Let’s fill the lot with Cadillacs!

Save the date for the NY-CT Two Rivers Region Summer Picnic on August 22nd. We’re gathering in Darien, CT, from 4 PM to 7 PM for an exclusive afternoon of "Good Cars, Good Friends, and Good Times."A reminder to members: This is a private event for CLC members and their guests. To maintain the privacy of our host, please refer to your upcoming club newsletter for the specific address and RSVP instructions.SPECIAL RESERVED CADILLAC PARKING let’s make the parking lot a show of its own!