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Points of Interest between Cheshire, Connecticut to New Milford, Connecticut

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picture of Cheshire, Connecticut

Five Unexpected Places to Stop on a Drive from Cheshire, CT, to New Milford, CT

Driving from Cheshire, Connecticut, to New Milford, Connecticut, offers a scenic and exciting journey that spans approximately 45 miles and takes around 1 hour. Along this route, you'll encounter charming towns, picturesque landscapes, and hidden gems that will make your journey worth it. Here are five unexpected places to stop on a drive from Cheshire, CT, to New Milford, CT.

1. The Switch Factory, Southbury CT

The Switch Factory is a historic tobacco factory turned contemporary shopping complex. It offers a unique shopping and dining experience, showcasing eclectic, locally owned businesses, breathtaking art installations, and fantastic music. This charming factory complex boasts artisanal bakeries, cafes, gift shops, art galleries, and numerous antique stores to explore. Don't forget to try the delicious sourdough bread from Flour Garden Bakery while enjoying the live music, and art shows on the second Friday of each month.

2. The Little Red Schoolhouse, Woodbury CT

Located in the historic district of Woodbury, The Little Red Schoolhouse is an iconic museum that takes visitors on a journey back in time. Built-in 1801, it was once the home of the town's first public school and has since been restored and turned into a museum. Here, you can see what the early days of education were like, complete with a variety of exhibits, artifacts, and interactive displays. After your visit, head over to Good News Cafe, a cozy restaurant located down the road from the museum. You'll love their cranberry walnut bread and savory turkey sandwich.

3. Lake Waramaug State Park, Kent CT

At Lake Waramaug State Park, you can indulge in nature's captivating beauty, serene calm, and recreational activities. This park features a beautiful lake that spans over 656 acres, surrounded by lush green forests and towering hills. There are numerous hiking and biking trails in the park, a beach area for swimming, and boating for those who love to fish. The park has a concession stand that serves a variety of refreshments, including homemade lemonade, popcorn, and hot dogs.

4. Goshen Fairgrounds, Goshen CT

Goshen Fairgrounds is where the annual Goshen Fair is held every Labor Day Weekend. This event has been attracting people from all over Connecticut for over a century. The Goshen Fairgrounds hosts various agricultural events and exhibits, showcasing farm animals, produce, woodworking, and photography. You'll also find unique craft vendors, live music, and thrilling carnival rides for the perfect family weekend getaway. Don't leave the fairgrounds without trying The Little Red Barn's apple cider donuts or classic fried dough.

5. Bull's Bridge, Kent CT

Bull's Bridge is a captivating historic landmark that dates back to 1842 and is listed on the National Register of Historic Places. It is a unique and picturesque stone arch bridge that spans over the Housatonic River, and it provides a breathtaking view that will leave you speechless. The bridge is situated within a park that has a hiking trail where you can meander through the forest alongside the river and take in the beautiful scenic views of the surrounding countryside. Over the bridge, you'll find the popular Bull's Bridge Inn, where you can quench your thirst with a refreshing pint and enjoy their infamous steak tips.

By now, you've visited five unique locations that are crucial to the historical and cultural heritage of Connecticut. The food, scenery, and entertainment options have been top-notch, with experiences that could keep anyone entertained for hours. Don't hesitate to embark on this pitstop-based journey the next time you're out exploring Connecticut.

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