Visit Essex, Connecticut: A Quaint New England Gem

All Aboard the Essex Steam Train

My first stop when visiting Essex was the historic Essex Train Depot. The Valley Railroad Company has operated the Essex Steam Train in the Connecticut River Valley since 1971. 

Arriving at the train station, I found plenty of free parking.

The station itself is a sight to behold, with its period-appropriate decor and friendly staff dressed in traditional conductor uniforms.

I made my way to the modern train depot to buy my tickets at the wooden window counter.

The Essex Steam Train departs three times daily, and I was lucky enough to snag a ticket just as it was about to leave.

The depot has this vintage vibe, like something out of a black-and-white movie.

TRIP TIP: Use the restroom before leaving the station, as a restroom is unavailable on the train.

The train is just as charming as the depot. With jet black gleaming cars with vintage details and cozy seating, the steam train is a sight to see.

I found myself in the coach car, greeted by an older gentleman dressed in full train engineer gear.

He didn’t just look the part; he acted it, too, narrating the journey with facts and stories about the Connecticut River Valley.

The train left the Essex train station and made its way along the Connecticut River Valley, passing through the charming towns of Chester and Deep River. 

While the trees weren’t quite in full fall color yet, they were hinting at the transformation to come. Along the way, I spotted swan-filled marshes, the impressive Gillette Castle, and the iconic Goodspeed Opera House.

One of the highlights was our stop at the Deep River Landing. This is where some passengers disembarked to board the Becky Thatcher riverboat for a scenic ride on the Connecticut River.

I decided to not take the riverboat ride this visit. But, luckily for me, I had a different treat.

I snagged a ride in the caboose on the way back.

The caboose only operates once a month, so it was a unique experience.

The caboose view is definitely worth it if you can get it.

Explore the Charming Town of Essex

After enjoying the Essex Steam Train, I headed to Main Street, the heart of Essex.

If I could bottle up charm and sprinkle it on a town, it would look just like this.

The streets are lined with historic homes, many with flowers spilling out of window boxes. The waterfront glistened in the afternoon sun, and every corner felt like it belonged on the cover of a travel magazine.

Essex, Connecticut, is often touted as one of the most beautiful small towns in America, and it’s easy to see why.

The village area is perfect for a leisurely walk while you admire the historic architecture, with some dating back to the 18th century.

It’s no wonder it has been used as the setting for several movies.

Lunch at The Gris

For lunch, I made my way to The Griswold Inn, or as locals lovingly call it, “The Gris.”

Established in 1776, it’s one of the oldest continuously operating inns in the United States.

Stepping into The Gris feels like stepping back in time.

The cozy taproom features a huge roaring fireplace. The walls are adorned with vintage maritime paintings.

And, overall, it’s just warm and inviting atmosphere.

The Griswold Inn offers a variety of dining options, from casual pub fare in the Tap Room to elegant dining in the Hunt Room.

You will be delighted by the menu selections and the friendly staff.

The menu is a mix of classic New England dishes, including clam chowder, lobster rolls, and prime rib.

Because it was mid-afternoon, I chose the butternut squash soup and split a giant chicken salad with my sister. Without asking, the waitress had the kitchen staff split the salad into two plates for us to share.

I love receiving this type of thoughtful service.

A Hallmark Channel Connection

The Griswold Inn’s timeless charm has not gone unnoticed by the entertainment world.

It has been featured in several Hallmark Channel movies, including Christmas at Pemberly Manor, perfectly capturing the inn’s quaint, romantic ambiance.

The Inn’s cozy atmosphere, historical significance, and picturesque setting make it a perfect backdrop for the heartwarming tales that Hallmark fans adore.

Exploring Essex

With full bellies, we set out to explore more of Essex.

The Connecticut River Museum is an easy walk from The Gris. Inside, you’ll get a fascinating look at the river’s history and the role it plays in shaping the area.

Plus, the waterfront views from the museum are stunning.

The walk and museum visit is a beautiful way to end your day in lovely Essex.

We spent the rest of the afternoon wandering through the town’s little shops.

Each shop had its own personality, filled with unique finds like handmade crafts, antiques, and local goodies.

Essex is the kind of place where you could buy something as simple as a mug, and it would instantly remind you of your visit.

Why Visiting Essex Stole My Heart

What struck me most about Essex was how peaceful and welcoming it felt.

It’s the kind of town that invites you to slow down and enjoy the moment. There’s a charm here that’s hard to put into words. You’ll feel it when you walk down its tree-lined streets or take in the historic colonial architecture.

It’s no wonder Essex has captured the hearts of travelers and earned a spot in 1000 Places to See Before You Die.

Final Thoughts About Visiting Essex, Connecticut

Whether you’re hopping on the Essex Steam Train, dining at The Griswold Inn, or simply strolling along the waterfront, Essex has a way of making you feel like you’ve stepped into another era. It’s a town that’s small in size but huge in charm.

If you’re planning a road trip to experience fall activities in Connecticut, don’t skip Essex. Better yet, make it a destination.

Trust me, you’ll leave with a camera roll full of gorgeous photos and a heart full of memories. And maybe, like me, you’ll be itching to come back before you’ve even left.