New England Travel: Best Road Trip Activities from Cheshire to East Hampton

Are you looking for an exciting and scenic road trip in Connecticut? Look no further than the route from Cheshire to East Hampton! This 42-mile journey will take you through charming villages, beautiful nature reserves, and historic landmarks. The halfway point of the trip in Meriden also adds to the fun. Check out the top five things to do on this road trip.

1. Hike in Hubbard Park

Hubbard Park is a 180-acre park in Meriden named after Walter Hubbard, a wealthy businessman who donated the land to the city in the early 1900s. The park’s main attraction is Castle Craig, a tower that offers a panoramic view of the surrounding countryside. But there’s much more to do here than just climb the tower. Visitors can explore the park’s hiking trails, picnic areas, and playgrounds.

Interesting fact: Castle Craig was built in 1900 and stands at 32 feet tall.

2. Visit the Shubert Theater

The historic Shubert Theater in New Haven has been a cultural icon in Connecticut since it opened in 1914. The theater has hosted many famous performers over the years, including Groucho Marx, Frank Sinatra, and Ella Fitzgerald. Today, the Shubert Theater is a not-for-profit organization that provides world-class entertainment and educational programs to the community.

Interesting fact: The Shubert Theater is one of the oldest operating theaters in the United States.

3. Explore Gillette Castle State Park

Gillette Castle State Park in East Haddam is home to a strange and fascinating building that looks like a medieval castle. The castle was built by William Gillette, a famous actor and playwright who wanted a place to escape the public eye. Visitors can tour the castle, which is filled with unusual gadgets and hidden passages, and stroll through the park’s beautiful gardens and trails.

Interesting fact: William Gillette was best known for his portrayal of Sherlock Holmes on stage.

4. Taste Wine at Arrigoni Winery

Arrigoni Winery in Portland is a family-owned vineyard that has been producing award-winning wines for over 20 years. Visitors can sip their way through the tasting room and enjoy views of the vineyard and countryside. The winery also hosts special events throughout the year, such as live music and art shows.

Interesting fact: Arrigoni Winery’s signature wine is a red blend called “Old Shagbark.”

5. Relax at Lake Hayward

Lake Hayward in East Haddam is a peaceful retreat that’s perfect for swimming, fishing, and boating. The lake is surrounded by wooded hills and has a sandy beach and picnic area. Visitors can rent kayaks and paddleboards or take a leisurely stroll around the lake’s perimeter.

Interesting fact: Lake Hayward was created in the late 1800s to provide water for a nearby paper mill.

This road trip from Cheshire to East Hampton can easily be done in a day, or you can take your time and spread it out over a weekend. The journey offers a unique mix of history, culture, and natural beauty that you won’t want to miss. So pack your bags, fill up the gas tank, and hit the road!