I've been a licensed driver here in Connecticut for 37 years, I was a traffic reporter on tv and radio for 10 years. I know these roads, and I love driving. We live in one of the most cramped parts of the country, a lot of our roads are horrible, but some are fun.

The Wolf logo
Get our free mobile app

I was driving through the Town Plot neighborhood in Waterbury, and just for fun, I took a ride down Chipman Street headed towards Oronoke Road. There's a little dip by the Old Colony Drive intersection that feels like you're on the Mad Mouse at Quassy for a second. My dad used to take us for a ride in his Caddy and make us all scream when it felt like we caught a little air there.

I started thinking about roads and streets around Connecticut that are fun to drive down. I thought of a couple that challenge your driving skills, one to catch a peaceful moment of Zen, and a couple that will satisfy your wanderlust, and why I think they're so fun.

The Roads That I Have The Most Fun Driving Around Connecticut

Some roads are just fun to drive down, right? It may be super steep, winding and challenging, or desolate and quiet if you need to chill out. Here are some of my favorite roads to drive down around Connecticut that I think are fun, and why they bring me joy.

Vintage Travelogue Reveals Connecticut in the 1960's

Have you wondered what our home used to look 60 years ago? I found a great vintage Travelogue called Connecticut Calling on YouTube from the early 1960's, take a look at some of the highlights that I found.

A Retail Therapy Road trip Around Connecticut

One of my favorite things to do on my days off is to discover and shop at new retail stores. Here are a few of my favorite streets around Connecticut to drive along and get a good dose of retail therapy

More From The Wolf