Essex Travel Guide: Things to Do, Best Time to Visit & Itinerary

Nestled on the banks of the Connecticut River, Essex is often cited as the “Perfect Small American Town,” a title it wears with effortless grace. Walking down Main Street feels like stepping into a living painting, where white picket fences frame Federal-style mansions and American flags wave gently in the river breeze. This is a place where history isn’t just preserved in museums; it is lived in the taverns, on the docks, and along the winding country roads.

The town’s maritime soul is palpable, rooted in a deep connection to the water that dates back to the Revolutionary War. Whether you are watching the morning mist rise off the river from the foot of Main Street or hearing the distant whistle of a steam train echoing through the valley, Essex offers a tranquility that feels worlds away from modern life. It is the quintessential New England escape, blending sophistication with small-town warmth.

A Legacy of Ships and Steam

Essex is defined by its relationship with the Connecticut River. In 1814, it was the site of a dramatic British raid during the War of 1812, an event known as the “Burning of the Ships,” where 27 American vessels were destroyed in the harbor. Today, the town commemorates this history with an annual parade, but the river is now a source of recreation rather than conflict. The deep-water anchorage makes it a premier destination for yachtsmen, while the preserved steam lines inland offer a window into the golden age of rail travel.

Beyond the history, the town exudes a cultural richness surprising for its size. From the nightly live music at the historic Griswold Inn to the art galleries dotting the village, there is a vibrant creative pulse here. It serves as a gateway to the wider Connecticut River Valley, a region designated by the Nature Conservancy as one of the “Last Great Places” in the Western Hemisphere due to its unspoiled beauty.

The Icons You’ll Want to See

Essex Steam Train & Riverboat - This is the town’s premier attraction, offering a 2.5-hour journey that combines a vintage train ride with a riverboat cruise. It sits about 0.5 miles from the town center. Tickets usually start around $40 per adult.

Connecticut River Museum - Located directly on the waterfront at the foot of Main Street, this museum offers deep insight into the valley’s ecosystem and history. It is the departure point for the Onrust sailing charter. Admission is approximately $12.

The Griswold Inn - Known locally as “The Gris,” this inn on Main Street has been serving travelers since 1776. It is a living museum in itself, housing an extensive collection of maritime art. Exploring the lobby and Tap Room is free, though buying a pint is recommended.

Pratt House - Located on West Avenue, just a 0.3-mile walk from the center, this 1732 home offers tours that showcase three centuries of Essex history. Admission is generally by donation or a small fee around $5 during open hours.

Planning Your Visit

Getting to Essex is best done by car, as it is located off Route 9, about two hours from New York City and two hours from Boston. While the Amtrak train stops in nearby Old Saybrook (about 10 minutes away), you will need a taxi or rideshare to reach Essex village. Once in the village, the downtown area is extremely walkable, with most shops, restaurants, and the waterfront located within a half-mile stretch of Main Street.

Pack layers regardless of the season, as the river breeze can cool things down in the evenings, even in summer. If you plan on dining at the more popular spots like The Griswold Inn or Carlson’s Landing, reservations are absolutely essential, especially on weekends and during the summer season. For a quieter experience, consider visiting mid-week when the pace slows down and the locals reclaim the town.

Essex shines brightest in the summer when the harbor is full of life, but the secret favorite season among locals is autumn. The foliage along the Connecticut River is world-class, and the crisp air makes walking the historic district a delight. Whenever you choose to visit, you will find a town that honors its past while warmly welcoming the present.