The Best Things to Do on a Road Trip from Cheshire, Massachusetts and Cornwall, Connecticut

Cheshire, Massachusetts and Cornwall, Connecticut are two neighboring towns that offer a lot of great sights and experiences to road trippers. The area is rich in natural beauty, quaint towns, historic landmarks, and diverse cuisine. Whether it’s a day trip or a weekend getaway, there are plenty of things to do and see in these towns and the surrounding areas. One of the highlights of the trip is the halfway point in Great Barrington, Massachusetts, a charming town that offers great food, culture, and shopping options. Here are the top five things to do on a road trip from Cheshire, Massachusetts and Cornwall, Connecticut.

Visit Tanglewood

Tanglewood is a music venue located in Lenox, Massachusetts, about 30 minutes from Cheshire. It is the summer home of the Boston Symphony Orchestra and hosts a variety of concerts and events from classical to pop music. Visitors can either enjoy the music from the Koussevitzky Music Shed or the lawn area, which has a capacity of up to 17,000 people. With stunning views of the Berkshire Hills, Tanglewood is a must-visit destination for music lovers. Interesting fact: Tanglewood has been the summer home of the Boston Symphony Orchestra since 1937, and has welcomed numerous famous performers and conductors over the years, including Yo-Yo Ma, James Taylor, and Leonard Bernstein.

Explore Mohawk Trail

Mohawk Trail is a scenic drive that runs for 69 miles through the Berkshire Mountains of Western Massachusetts. Starting from Williamstown, visitors can enjoy beautiful views of forests, rivers, and waterfalls, as well as historic sites and charming towns along the way. The trip includes a number of scenic overlooks and hiking trails, including the famed Chapel of the Holy Cross. Interesting fact: Mohawk Trail has a rich history that dates back to the Native American period, and it was once used as a trade route between the Connecticut River Valley and the Hudson River Valley.

Visit Lime Rock Park

Lime Rock Park is a historic racetrack located in Lakeville, Connecticut, about 20 minutes from Cornwall. It was originally built in 1956 and has held numerous professional and amateur races over the years. Visitors can watch races from the stands or the infield, and there are often events and festivals held at the park as well. Interesting fact: Lime Rock Park is one of the few remaining road courses in the country that has maintained its original configuration over the years.

Learn about Mark Twain

Mark Twain House and Museum is located in Hartford, Connecticut, about an hour from both Cheshire and Cornwall. It was the home of Samuel Clemens, aka Mark Twain, from 1874 to 1891, and is now a museum dedicated to his life and works. Visitors can take a guided tour of the house and learn about Twain’s life, writing, and legacy. Interesting fact: Mark Twain House and Museum is also home to the largest collection of Mark Twain artifacts in the world, including original manuscripts, letters, and photographs.

Hike Bear Mountain

Bear Mountain is the highest peak in Connecticut, at an elevation of 2,316 feet. Located in Salisbury, Connecticut, about 30 minutes from Cornwall, it offers stunning views of the surrounding landscape, including the Catskills and the Taconics. The hike is challenging but rewarding, and there are several trails to choose from, ranging from 3 to 6 miles in length. Interesting fact: Bear Mountain is part of the Appalachian Trail, a 2,200-mile hiking trail that runs from Georgia to Maine.

In conclusion, a road trip from Cheshire, Massachusetts and Cornwall, Connecticut offers a wonderful blend of natural beauty, history, culture, and entertainment. The trip can be completed in one day, but to fully enjoy all that the area has to offer, visitors may want to consider staying overnight. Regardless of the length of the trip, there are plenty of things to see and do, and the journey itself is just as rewarding as the destinations.