Indie Energy, New England Charm, A Fun Main Street, And Waterfront Views Blend In This Connecticut City

New England is home to some of the oldest settlements in the United States, and the state of Connecticut holds many of these colonial relics. During the 17th century, two early communities were Connecticut's historic capital city, Hartford, and the beloved beach town of Old Saybrook. At the halfway point between these two places became a village now known as Middletown. It's name originated from its proximity to these towns, and today, it's conveniently accessible by car or bus from Bradley International Airport in Hartford or the Northeast Regional Amtrak train line in Old Saybrook. 

Since its early days, Middletown has grown into a small city and become a hip university town with a flourishing arts scene, all while maintaining its New England roots and charm. Wesleyan University was founded in 1831 and quickly became a hub for arts, academics, and athletics. The university's influence, combined with the scenic waterfront location and commercial Main Street, have created a place where indie artisan culture thrives in a quintessential New England environment.

On the first Friday of every month, Middletown's Main Street transforms into a showcase — aptly named First Fridays — for the indie influence of the city. Events ranging from live music to local vendor pop-ups take over and offer a diverse agenda for wide-ranging crowds. The music scene also expands to independent venues in the city such as the Buttonwood Tree Performing Arts Center, which hosts local bands, theater productions, and other performing arts shows, adding to the broader list of Connecticut concert venues.

Middletown's centuries-old history, and former site as a shipbuilding hub, made it a popular home for military and business officials. Colonel Clarence Wadsworth and General Joseph King Fenno Mansfield are two such individuals who maintained large mansions in the town that are now museum attractions — the Wadsworth Mansion and General Mansfield House, respectively — capturing the old New England architecture and feel. The town's concentration of museums also includes the KidCity Children's Museum and the Greater Middletown Military Museum, offering fun and educational outlets for visitors of all ages. The juxtaposition of historic ambiance and modern energy is evident throughout the city and creates a variety of attractions ranging from shopping, music, and museums in urban areas to the tranquility of the riverfront. 

In addition to First Fridays, Main Street in Middletown is home to a myriad of dining and shopping gems. During the summer, it hosts a weekly farmers market supporting community farms and offering fresh local produce. The thoroughfare is still a bustling destination even when pop-ups or markets are not active, with a diverse restaurant scene including Asian fusion destinations like Mikado Sushi Bar and Typhoon, Italian and Mexican spots like Cantina Cafe and Coyote Blue, and traditional American joints such as Eli Cannons Tap Room and Haven Hot Chicken. Even when businesses are empty, the area has something to show: The Downtown Business District Storefront Project is a local initiative that converts vacant storefronts into temporary art installations, further showcasing the commercial and artistic draw of the city. 

The Connecticut River is known for idyllic New England towns, and Middletown is a prime example of these destinations. The riverfront lies just north of Main Street and contains pristine views, pedestrian walks, and the waterfront Harbor Park. The city has been working on the "Return to the Riverbend" plan since 2021 and has improved transportation and land use along the riverside to make the area more accessible and enjoyable for all.