Cars and Coffee Darien, Goodwives Shopping Center

Cars and Coffee Darien gathers once a month, April to November, at Goodwives Shopping Center, 25 Old Kings Highway North in Darien, Connecticut. The organizer’s Facebook page describes the rule as “the 2nd Sunday of every month from April to November at the site of the last Cannonball.” The organizer’s website posts the full season schedule, with a theme for each month.

The next date breaks the Sunday pattern. The 2026 season ends with the Cannonball Run Reunion on Saturday 14 November, from 6:30am to 10:30am, per the organizer’s event page. The website’s season note says the gatherings run until 8 November, but the schedule and the event page both give 14 November, and the event page is the more specific.

When to arrive

For the reunion, the organizer gives 6:30am to 10:30am and says early arrivals are welcome. The program lists a DJ, a live memorabilia auction and a question-and-answer session with original Cannonball participants.

The regular monthly dates run on a tighter clock. For October 2026 the organizer listed 7am to 10:30am, with gates opening at 6:30am. Show cars had to be on the field by 7:30am to be eligible for an award, judging began at 8am, and awards were given at 10am.

What it costs

The reunion’s event page says show cars pay $25 in advance or $30 on the day, and spectators pay $5. Children under 12 and active-duty military get in free. The same page’s price summary reads $20 to $30, and it also sells advance VIP parking at $25, so check the ticket options before you buy. The organizer says all profits from the reunion go to the Brock Yates Foundation for Alzheimer’s research.

The regular monthly dates are ticketed too. The October 2026 event page listed a cost of $10 to $20. The website says registering your car gets your coffee free.

The lot

The meet uses Goodwives Shopping Center, which the organizer also calls Old Mill Center, at 25 Old Kings Highway North. It is a working shopping center, so park where you are directed and keep store entrances clear.

The coffee

Coffee and breakfast come from Aux Delices, per the organizer. Everyone who attends gets a lanyard and badge good for 20% off breakfast goodies there.

How it started

The organizer’s website explains the choice of lot. In the 1970s and 1980s Goodwives held a restaurant called the Lock, Stock and Barrel, owned by Darien resident George Lysle, who managed racing careers at IMG. The restaurant became a hangout for local motorsports enthusiasts, and in 1979 it was the starting point for what the organizer calls the last “official” Cannonball. That is why the season ends with a reunion. The 2026 event is the fourth.

Before you go

The organizer is blunt: “Do not plan on coming if your plan is to show off how fast your car is or how loud your exhaust is. Police will be on site, and anyone engaging in risky behavior will be permanently banned from attending future events as an exhibitor.”

Weather decides dates here. The September 2026 date was cancelled for rain and the October date was cancelled as well. The website offers text alerts for cancellations and time changes, which is the quickest way to know on the morning.

Any year, make and model of car or motorcycle is welcome, and the organizer encourages bringing children and pets.

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