Five Unexpected Places to Stop on a Drive from Cheshire, Connecticut to Fairview, Pennsylvania

Have you ever embarked on a road trip that took you through unexpected but amazing places? Cheshire, Connecticut, to Fairview, Pennsylvania, is not one of the most popular routes for travelers, but it offers a unique experience like no other. The trip, which takes about six hours, is an opportunity to explore some beautiful towns and attractions. Here are five unexpected places to stop and spend some time during your trip.

The Halfway Point: Middletown, NY

Middletown, NY, is the perfect halfway point between Cheshire, Connecticut, and Fairview, Pennsylvania. This compact city offers plenty of options for a relaxing break from the road. It features a great mix of outlets, local shops, and unique boutiques. Middletown is also home to many world-class restaurants. A must-try is Tony Boffa's Restaurant, a family-owned establishment with fantastic Italian food and an unbeatable charming atmosphere. If you are traveling with kids, head to the Enchanted Forest Water Safari, a family-run water park that has been an area icon for over 60 years.

1. Milford, PA: Art and Nature Mix

Milford, PA, is an ideal place to break your journey. This small town combines art and nature, offering something for everyone's taste. Milford is renowned for its thriving arts scene, with several galleries and shops showcasing local paintings, sculptures, and crafts. It is also home to the Grey Towers National Historic Site, a stunning estate surrounded by acres of stately forests and scenic waterfalls. Treat yourself to a cozy lunch or dinner at the Hotel Fauchere's Delmonico restaurant, a local favorite for classic American food with a touch of French sophistication.

2. Jim Thorpe, PA: A Town with a Story to Tell

Jim Thorpe is a former mining town that has preserved its unique charm and attractions. It boasts several historic sites, including The Old Jail Museum, where prisoners lived in abject conditions until 1995. The Asa Packer Mansion showcases the life and times of one of America's most successful businessmen in the mid-19th century. Jim Thorpe is also a gateway to some of the area's most picturesque hiking and biking trails, with the Lehigh Gorge State Park providing miles of scenic beauty. Stop by Moya, an Irish pub, and restaurant that offers traditional Irish food in a casual and fun atmosphere.

3. Allentown, PA: A City of Art and Culture

Allentown, PA, is a city that strives to showcase its art and cultural heritage. It is home to the Allentown Art Museum, a functional art space featuring local and international art, including Ralston Crawford's ‘construction’ in 1950. The museum hosts several events throughout the year, making it an excellent place to visit more than once. Another must-visit is the Allentown Symphony Hall, a magnificent concert hall that seats up to twelve hundred people. Immerse yourself in a world of live music and excellent acoustics. Indulge in a yummy meal at The Dime, a chic and sophisticated venue known for its upscale American cuisine.

4. Harrisburg, PA: A City of History and Beauty

Harrisburg, the capital of Pennsylvania, is one of the most underrated cities in America. The city's most iconic landmark is the Pennsylvania State Capitol Building, which boasts stunning architecture and design. Harrisburg also features several historic sites, including the National Civil War Museum and Fort Hunter Mansion & Park. It is a paradise for nature lovers, with miles of scenic biking and hiking trails at Wildwood Park. Sink your teeth into some of the best seafood in the city at Devon Seafood + Steak, a classic and refined venue.

5. Hershey, PA: The Sweetest Place on Earth

Hershey, PA, is a top tourist destination that attracts millions of visitors every year. Its charming and whimsical atmosphere gives visitors everything from amusement parks, top-rated restaurants, and chocolate factory tours. At Hershey's Chocolate World, you can learn about the history of Hershey's chocolates and even create your confectionery masterpiece. Hershey's also has top-rated eateries, including The Circular at The Hotel Hershey, which ranks as a local favorite for brunch and fine dining.

When considering the many routes you could take, a road trip from Cheshire, Connecticut, to Fairview, Pennsylvania, might not be the first that comes to mind. However, the above roadside destinations in the Northeast make it one of the most memorable journeys you can experience. So, pack your bags, fill up your car, put on your favorite tunes, and get exploring. The road trip from Cheshire, Connecticut, to Fairview, Pennsylvania, will leave you with unforgettable memories and experiences.