Connecticut's Valentine's Train Rides

Published: February 1, 2026

The Essex Steam Train & Riverboat offers one of New England’s most immersive railroad experiences: vintage coaches rolling through river-country scenery, a working heritage railroad with deep local roots, and—when you want to turn a ride into a true occasion—full-service dining aboard the Essex Clipper Dinner Train. Operated by the Valley Railroad Company, the attraction has been welcoming visitors to the lower Connecticut River Valley for decades, preserving the feel of classic rail travel while packaging it into a fun, approachable outing for first-timers and railfans alike

Valley Railroad 2-8-0 #97 leads a northbound excursion up the Connecticut River Valley. Howard Pincus photo.

About The Railroad

Essex has the sort of small-town charm that seems tailor-made for a train trip: clapboard buildings, marinas and river traffic nearby, and that unmistakable shoreline atmosphere. The station area sits close to the water, but the moment your train departs you’re quickly wrapped in the quieter landscapes that define this region—woodlands, wetlands, and open views that change dramatically with the seasons.

What makes the Essex Steam Train stand out is how much it feels like an experience rather than a simple point-A-to-point-B ride. The railroad is known for pairing rail excursions with other activities and seasonal programming, giving families and couples reasons to return throughout the year. The result is a destination that works equally well as a day trip, a celebratory night out, or a “we need something different to do this weekend” escape.

The Essex Clipper Dinner Train

If the standard excursion is about scenery and nostalgia, the Essex Clipper Dinner Train is about ambiance—an old-school, special-occasion kind of night where the table is set, the rhythm of the rails provides the soundtrack, and the meal arrives course by course while the countryside slips by your window.

According to the railroad, the Essex Clipper features a four-course meal served in restored 1920s Pullman dining cars, typically on a 2 to 2½-hour journey, with service designed to evoke the heyday of streamlined timetables and white-tablecloth rail dining. It’s pulled by a vintage diesel locomotive, which gives the train a classic “mainline dinner run” vibe—steady, smooth, and perfect for lingering over dessert.

The tone is intentionally unhurried. This isn’t a quick bite before the ride; the ride is the evening. You settle in, watch the world roll past, and let the staff take care of the details—exactly what you want if your goal is to reconnect, celebrate, or simply trade screens for scenery.

Why These Trains Are So Popular

A good dinner train needs more than a menu. It needs a route that’s visually rewarding in fading afternoon light, cars that feel authentic, and a pace that lets the experience breathe. The Essex area delivers on all three. The lower Connecticut River Valley is scenic without being overwhelming; it’s a place where you can actually talk, laugh, and enjoy the ride. And because the Essex Clipper uses classic dining cars, there’s a built-in sense of occasion the moment you step aboard—like you’ve slipped into a different era, even if only for a couple of hours.

For visitors, that “step back in time” feeling is part of the appeal of the larger Essex Steam Train & Riverboat experience. For rail enthusiasts, it’s also a chance to enjoy heritage equipment doing what it was built to do: carrying passengers in comfort, not sitting silent behind ropes.

Valentine’s Day Spotlight: The Essex Clipper Dinner Train Romance Run

When February arrives, the Essex Clipper becomes a centerpiece event: Valentine’s Day Dinner Trains designed specifically for couples (and anyone who loves a romantic evening out). The railroad frames it as a 2½-hour dining excursion with “the romance of rails and vintage train cars” setting the scene, beginning with appetizers and continuing with a plated entrée selection. 2026 Valentine’s schedule and departure times

For the upcoming Valentine’s season, Essex Steam Train lists multiple opportunities to ride:

February 12, 13, 14 @ 6:00 pm
February 14 & 15 @ 12:00 pm (midday departures)

That mix is a big plus. If you want a classic “date night” feel, the evening departures are ideal. If you prefer a daylight ride—especially for winter scenery and photos—the midday options offer a more relaxed, bright-window version of the same dining experience.What’s on the Valentine’s menu

Essex Steam Train’s Valentine’s offering is designed around choice, with entrée options that feel appropriately celebratory. For the Valentine’s Day Dinner Train (Feb. 12–15, 2026), the published entrée selections include:

Steak au Poivre (NY strip with brandy demi-glace)
Chicken Rollatini
Potato and Crab Crusted Salmon
Butternut Squash Ravioli

From a practical standpoint, that range makes it easier for couples to treat this like a true “special dinner out,” even if you have different tastes (or dietary preferences) at the table. It also keeps the mood elevated—this is more “Valentine’s celebration” than “quick bite before the show.”

Pricing and how it’s presented

Essex Steam Train’s event listing for a Valentine’s dinner departure shows a per-person ticket price (for at least one of the Valentine’s date listings) of $149.99.
Because dinner trains can sell quickly—especially around Valentine’s weekend—the best strategy is to pick your preferred departure time first (evening vs. midday), then book as early as you can. To learn more about their Valentine's Day dinner trains please click here to visit their website.