Connecticut Wine Tasting Train Rides

Published: February 2, 2026

Set in the historic river town of Essex, Connecticut, the Essex Steam Train is one of New England’s best “time machine” experiences—part living railroad museum, part scenic excursion, and (when you want it to be) a surprisingly elegant night out. Operated by the Valley Railroad Company, the attraction runs over the former Connecticut Valley Railroad line and has been welcoming passengers to the lower Connecticut River Valley since the early 1970s.

What makes the operation especially appealing is its variety. You can keep things simple with a narrated sightseeing trip, pair the rails with a boat cruise, or lean into the golden-age vibe with a linen-tablecloth meal in classic dining cars. And if you’re looking for a signature “special occasion” experience, their Wine & Chocolate Dinner Train stands out as a decadent, social, and distinctly memorable take on dinner on the rails.

A Brief History

Many scenic railways are built on lines that vanished long ago. What’s unique here is that the underlying railroad story reaches back into the 19th century. The company’s own history notes that the Valley Railroad has existed “in one form or the other since 1868,” reflecting the changing fortunes of American railroading from the steam era onward.

Fast-forward to the preservation era: the heritage operation most visitors know today began in 1971, when excursion service started between Deep River and Essex. Over time, additional portions of the line were reopened, and the railroad developed into a full-featured visitor destination with multiple train experiences and seasonal events.

That sense of continuity is part of the appeal. You’re not riding a “theme park train”—you’re traveling on a historic corridor through towns and landscapes that still feel quintessentially New England.

Trains & Riverboats

For first-time visitors, the most iconic outing is the Train & Boat experience. The journey begins at the historic station (often highlighted as an 1890s-era depot) and heads out on a narrated round-trip through Deep River and Chester, rolling past marshes, woods, and river vistas. A signature highlight is Selden Neck State Park—a largely undeveloped island park that’s only accessible by boat, giving the whole trip a pleasantly “you can’t do this by car” feel.

Depending on the schedule, you may choose a train-only excursion or combine the train with a riverboat cruise—an easy way to turn a couple of hours into a half-day outing. The scenery does a lot of the work: the lower Connecticut River Valley is the kind of landscape that feels custom-built for slow travel, especially in peak foliage or warm-weather months.

Dinner on the rails: The Essex Clipper

If the daytime rides feel like a moving postcard, the evening dining service feels like stepping into a different era of travel altogether. The railroad’s flagship dining experience is the Essex Clipper Dinner Train, operating in restored, 1920s-style Pullman dining cars and pulled by a vintage diesel locomotive. The ride typically lasts about 2 to 2½ hours, with full table service and a multi-course meal designed to make the journey itself the main event.

The tone is intentionally unhurried—more “anniversary dinner” than “quick bite before a show.” The railroad describes it as a chance to relax and reconnect while the rhythm of the rails does what it has always done best: turns ordinary distance into an experience.

Menus vary through the year, and the railroad posts seasonal selections for its dinner trains. For example, their winter dinner train menu listings include options such as prime rib, chicken cacciatore, seared salmon, and butternut squash ravioli (with the usual dinner-train staples like appetizer, salad, dessert, coffee, and water).

That rotating menu approach is a big plus—it gives repeat visitors a reason to come back, and it lets the kitchen lean into seasonal comfort food when Connecticut nights turn crisp.

Wine & Chocolate Dinner Train

Now for the headliner: the Wine & Chocolate Dinner Train is essentially the Essex Clipper experience turned up a notch—part fine dinner, part guided tasting, part dessert-forward celebration.

Here’s the core idea: you board the vintage dining train for a specially created three-course dinner, then settle in for a curated pairing experience led by a guest wine steward. As the evening unfolds, a guest chocolatier joins the program to introduce chocolate pairings designed to complement the wines—turning the meal into a guided, conversation-friendly tasting event rather than “just” dinner service. What makes it different from a standard dinner train?

1) It’s hosted, not just served

The presence of a wine steward and chocolatier changes the energy in the cars. Instead of courses arriving quietly, you get context—what you’re tasting, why it works, and what to notice.

2) It’s built around pairing

Chocolate can be tricky with wine when you’re doing it on your own. A curated pairing makes it easier to appreciate the contrasts—fruit versus cocoa, sweetness versus tannin, creamy textures versus bright acidity—without needing to be an expert.

3) It’s ideal for couples and groups

This is one of those rare date-night experiences that also works for double-dates, birthdays, and friend groups, because the guided tasting gives everyone something to talk about.The featured chocolatier

The railroad’s description specifically mentions pairing guidance from Fascia’s Chocolates, a well-known Connecticut chocolatier that appears in multiple Essex-themed pairing events. Duration and pricing (what to expect)

The Wine & Chocolate Dinner Train is generally promoted as a roughly 2½-hour experience. Pricing can vary by season and offering; one current listing shows $159.99.

Because these are special-event departures (and not nightly service), availability can be limited—so it’s the kind of outing you plan a bit more like a concert reservation than a typical dinner reservation.

Final Thoughts

Plenty of scenic railroads offer special meals. Fewer deliver a complete package: historic corridor, restored dining cars, a true sense of occasion, and a themed program that’s more than a novelty. With the Essex Clipper as its foundation—and the Wine & Chocolate Dinner Train as a standout variation—the Essex operation has built an experience that feels both classic and current: old-school rail travel aesthetics paired with the modern appeal of guided tastings and local chocolate. To learn more about this experience please click here to visit the railroad's website.