The Ultimate Connecticut Adventure: Road Tripping from Cheshire to Roxbury!

Imagine embarking on an exciting road trip across the picturesque landscapes of Connecticut, from the lively town of Cheshire to the charming village of Roxbury. With multiple routes to choose from, you'll have the freedom to explore the state's hidden treasures and create wonderful memories along the way. So buckle up, grab your map, and let's hit the road!

Route #1: The Scenic Serenade

If you're in the mood for a leisurely drive that will take your breath away, Route #1 is the ideal choice. Spanning approximately 28 miles, this scenic journey promises enchanting vistas and peaceful countryside exploration. Allow yourself around 45 minutes to 1 hour for this delightful adventure.

After leaving Cheshire, head west on I-84 towards Waterbury, where you'll soon be greeted by the rolling hills and lush valleys of the Litchfield County. As you bask in the beauty of your surroundings, consider making a quick pit stop at the Black Rock State Park in Watertown. With its picturesque trails and serene lake, it's the perfect spot for a refreshing hike or a peaceful picnic.

Route #2: The Historic Heritage Trail

For history buffs and culture enthusiasts, Route #2 promises a journey filled with captivating tales and significant landmarks. Covering around 30 miles, allow yourself approximately 50 minutes to 1 hour and 15 minutes to fully indulge in this historical escapade.

Start your adventure by taking I-691 West from Cheshire, passing through the charming town of Meriden. Just a short detour from your route lies the remarkable Hubbard Park, where you can revel in the beauty of its grand Castle Craig structure and immerse yourself in nature's splendor.

Continuing your journey westward on Route 322, you'll pass through Middlefield before reaching Durham, where you can witness the stunning architecture of the historic Durham Congregational Church. Take your time to explore the town's quaint streets or grab a bite to eat at one of the charming local restaurants.

Route #3: The Quaint Connecticut Quicksilver

For those seeking a shorter and more direct route, Route #3 will have you arriving in Roxbury in no time! This 17-mile adventure should take you around 30 minutes to 45 minutes.

Begin your journey south on CT-10 from Cheshire, cruising along the peaceful Connecticut countryside until you reach the charming town of Southbury. Make a stop at the Southbury Green Shopping Center, where you can satisfy your cravings at one of the delightful eateries or peruse the eclectic mix of shops.

From Southbury, head west on Route 67, relishing in the lovely rural scenery as you travel through the small towns of Bridgewater and Brookfield, before finally reaching your destination in picturesque Roxbury. Once there, take a stroll through the town center, admiring the historical buildings that have stood the test of time.

However you choose to reach Roxbury, you can expect to be captivated by the unique charm and tranquility this village offers. So, rev up your engines, put on your favorite playlist, and let the road guide you to a memorable Connecticut adventure like no other!