The One Connecticut Town Everyone Should Visit At Least Once

Connecticut is a state shaped by water, hillsides, and small towns that have been both witness and participant in important American history. While many places across the state offer a piece of that story, one town brings it all together with unique preservation and style. Set along the Connecticut River, this historic town combines maritime heritage, detailed architecture from past eras, and cultural opportunities within a compact, walkable setting. Rather than presenting history as something to observe from a distance, Essex welcomes travelers to experience it through everyday life and allows them to participate in longstanding traditions. Keep reading to discover how this town has earned its place as a town that everyone should visit at least once.

Essex

In the many cities and townships that create the cozy kingdom of Connecticut, Essex stands alone. Cradling the banks of the Connecticut River, this historic town is rich with wonders both big and small. It’s impossible to bypass the small details, such as the classic colonial architecture that turns a stroll down the street into a portal through time. Essex is composed of three villages: Essex Village, Centerbrook, and Ivoryton.

In each village, the homes, Inns, and even steam trains give visitors that rare nostalgic feeling that cannot be found anywhere else. The Essex Steam Train and Riverboat keeps the local maritime and industrial heritage alive with vintage locomotives and coaches that give guests a luxurious way to connect with the past while appreciating the waterway that is so integral to the town's thriving culture and ecosystem. Passengers who select a dining option get a four-course meal within a restored 1920s car, while taking a riverboat voyage offers a gorgeous view of the river as well as the green rolling land that surrounds it.

Back on land, see a show where locals have gathered for performances for over a century, at the Ivoryton Playhouse. While this theater has hosted many celebrities and won many awards, it is most loved for its bold productions. After seeing a show, learn about the history of the state's titular river at The Connecticut River Museum. The non-profit museum tells the story not only of the important waterway, but also of the generations of people who steward and sustain life from the river. Exhibits explore topics ranging from Indigenous stewardship and early colonial history to the river’s role as a vital natural resource, to a vertical mural inspired by folk art.

Where to Stay in Essex

While staying in Essex, choosing accommodations that reflect the town’s historic character enhances the overall experience. Travelers drawn to classic New England charm will feel especially at home at The Griswold Inn, one of the oldest continuously operating inns in the country. With its dark wood interiors, traditional furnishings, and welcoming common spaces, the inn has served as a gathering place for sailors, artists, and visitors for more than two centuries. Staying here offers a rare opportunity to experience Essex much as travelers once did, while still enjoying modern comforts.

For a quieter, more intimate stay, The Copper Beech Inn provides a refined bed-and-breakfast experience set within the Connecticut River Valley. Known for its award-winning restaurant and serene surroundings, the inn offers peaceful accommodations focused on relaxation and wellness. Guests are treated to scenic views, attentive service, and a sense of retreat that pairs well with Essex’s slower pace and natural beauty.

Exploring Nearby

Follow the Connecticut River for 5 miles to find Chester, a whimsical town where community art and scenic natural landscapes merge seamlessly. Full of hidden streams, waterfalls, and art galleries, this small town makes enjoying the abundance of the wild easy and comfortable. Just a fifteen-minute drive away, find one of Connecticut’s oldest towns, Old Saybrook. Settled in 1635, this waterfront gem is full of beaches and lush coastal forests to traverse alongside luxury experiences at spas and resorts. Finally, see the town whose charm has made its way to audiences around the world through the popular film “Mystic Pizza”. Mystic is a seaport village where travelers by land and sea have enjoyed the local eateries and thriving culture for hundreds of years. Many annual events take place throughout the year, where the community celebrates music, art, cuisine, and much more.

More Than a Photograph

What makes Essex such a special town is more than the coastline, architecture, and hills that appear in photographs. It is a place shaped by movement. Movement of water, of people, and of time itself. Along the Connecticut River, traditions continue not as reenactments, but as part of daily life. Whether exploring its villages on foot or learning its stories through cultural institutions, visitors find a town that feels both intimate and enduring. Essex offers a rare chance to slow down and experience Connecticut’s history as something still unfolding.