Romance And History Meet At Essex Steam Train And Riverboat

Men's Dating

Essex Steam Train & Riverboat — Creating Romantic Experiences Where Couples Can Learn About Connecticut’s Cultural Heritage and Each Other

Kara Pound

Written by: Kara Pound

Kara Pound

Kara Pound is an award-winning journalist based in St. Augustine, Florida. She holds a bachelor's degree in journalism from Flagler College. Her work has been published in INKED, Natural Awakenings, Design Aglow, Memphis Flyer, Jacksonville Magazine, E/Environmental Magazine, and dozens more. Check out some of Kara's work at

Edited by: Lillian Castro

Lillian Castro

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The Short Version: Travel by train into the heart of the unspoiled Connecticut River Valley on a unique two-and-a-half hour journey that begins at the historic 1892 Essex Station. Aboard the elegant Essex Clipper, you and your date will enjoy a four-course meal while gazing at soothing scenery and creating one-of-a-kind memories. This is just one of the many extraordinary offerings of Essex Steam Train & Riverboat

Long before air travel and automobiles, trains were the predominant means of transportation in America. From double-stack cargo containers to opulent sleeper cars carrying the country’s richest families on the First Transcontinental Railroad, trains have a long and colorful history. For the folks at Essex Steam Train & Riverboat, the bygone days of rail travel make for a unique present-day excursion perfect for romantic dates and one-of-a-kind wedding celebrations.

“Everyone here takes a ton of pride in providing the best experience for our customers that we possibly can,” said Maureen Quintin, Director of Communications for Essex Steam Train & Riverboat. “We love coming up with new ideas, new events, and trying to appeal to different demographics.”

The Valley Railroad Company has been in existence in one form or another since 1868. Founded by James C. Walkeley, President of Charter Oak Life Insurance, the rail line was built through the beautiful Connecticut River Valley with its first ceremonial train run in July of 1871. Exactly a century later, the railway was granted service to Essex Steam Train & Riverboat and has been steaming ever since.

Today, the company offers an eclectic array of exceptional experiences from its popular Swallow Sunset Cruises aboard the Becky Thatcher Riverboat to fall foliage expeditions along the countryside on vintage train coaches.

“We want people to know — and find out through visiting — that we’re a destination offering different adventures along the Connecticut River,” Maureen said. “It’s not somewhere that you just want to visit once, but come back time and time again.”

Unique Settings Perfect for First Dates and Making Memories

A first date is nerve-racking. You’ve met a person you’re interested in getting to know better, found the perfect outfit, and gone over all the conversation topics that might make a good impression. Now it’s time to choose a location for your first encounter. Sure, an upscale steakhouse is nice. But it can be intimidating sitting across from someone you barely know. Why not suggest an experience that lends itself to making memories to last a lifetime?

“It’s like a step back in time,” Maureen said of a rendezvous on one of the many trips that Essex Steam Train & Riverboat has to offer. “I think it is more of an adventurous date than simply going out for a bite to eat.”

Check out the Gillette Castle Connection, a seasonal day-trip that takes you on a 30-minute train ride through the serene Connecticut River Valley to the Hadlyme Flagstop where you will detrain for a short walk to the Chester-Hadlyme Ferry. Once aboard, you’ll be transported to the base of Gillette Castle State Park for a unique hiking experience to Gillette Castle, home of the late William Gillette, famous for his stage portrayal of Sherlock Holmes.

If you’re more of a low-key couple, there are also popular lunch excursions where you and a date will enjoy a three-course lunch aboard restored 1920’s Pullman dining cars as part of a nearly four-hour train ride and riverboat sightseeing trip that embarks at Deep River Landing.

“We also offer a dinner train, which is really romantic,” said Maureen. “It’s a breathtaking journey through the valley and a great way to get to know someone.”

Seasonal Excursions for the Ultimate New England Experience

With each seasonal change, the team at Essex Steam Train & Riverboat puts their heads together to come up with new and exciting tours to keep couples coming back time and again.

“In the summer, we offer so many things for couples to do,” Maureen said. “We have sunset Cigar & Whiskey Cruises in June and July, a Wine and Chocolate pairing cruise in August, and Beer & Brats cruises in September and October. We also do sunset cruises throughout the summer with live music onboard for a nice, romantic date night.”

The popular Chocolate & Wine Cruise features a train ride from Essex Station to the Becky Thatcher Riverboat for a one-and-a-half-hour cruise where passengers will enjoy delectable chocolates and fine wine pairings.

If fine cigars and brown spirits are more your thing, check out the Sunset, Cigars & Whiskey Cruise as premium whiskeys are paired with hand-rolled, Connecticut-wrapped cigars provided by Up in Smoke along with food provided throughout the evening, during a two-hour cruise on the Connecticut River.

Other notable activities include Rhythm by the Rails, a live concert series throughout the summer on the lawn of Essex Station, as well as the Brats & Beer Cruise, joining grilled brats with an array of local brews, and East Haddam Concert Express for a trip to Eagle Landing State Park in Haddam, Connecticut, for an evening of live music.

All Aboard: Plan Your Visit to Blow Off Some Steam

It’s no secret that Connecticut and other areas of New England bustle with tourists throughout different times of the year. Essex Steam Train & Riverboat adventures are a bit off the beaten path and make visiting the Connecticut River Valley a stress-free endeavor for you and your significant other.

Headquartered in Essex, a small town in South Central Connecticut, the attraction is easy to get to via car or through the Old Saybrook Train Station, which is served by both Amtrak and Shoreline East railroads.

There are plenty of places to stay, too. Check out the Griswold Inn, one of the oldest continuously operated inns in the country established in 1776 that combines historic accommodations with modern amenities. There’s also Copper Beech Inn, a renowned award-winning inn located along the Long Island Sound shoreline and close to charming shops and restaurants.

After a full day of vintage train rides and peaceful riverboat rides, stop at a local watering hole for a bite to eat at one of the many eclectic eateries. The Blue Hound Cookery & Tap Room in Ivoryton, Connecticut, features coastal fare with a New Orleans flair. Penny Lane Pub in nearby Old Saybrook is a down-home gastropub with English-style bar fare and plenty of outdoor seating.

Essex — An Ideal Destination to Celebrate Life’s Special Moments

With a laundry list of offerings and unparalleled locales Essex Steam Train & Riverboat boasts, it’s no surprise that brides and grooms all over the world are choosing it as the location for their “I Dos.”

“The biggest draw is our unique environment,” said Maureen. “Our industrial, steampunk kind of atmosphere lends itself to a variety of great spots for unique wedding photos. We have full catering service here on-site and an event coordinator who can help you plan the entire thing from beginning to end.”

From an outdoor ceremony on the lawn at Essex Station to cocktail hour aboard the Becky Thatcher Riverboat to a small-scale reception on a vintage train, there are endless opportunities to celebrate life’s special moments, including anniversaries, milestone birthdays and weddings. The site’s two indoor venue spaces include the Oliver Jensen Gallery, which is a smaller space, and River Valley Junction, which can fit up to 200 guests for a buffet dinner.

“We’re really enthusiastic about using local vendors and happy to give recommendations to anyone — especially couples coming from out of state,” Maureen said. “We’ve had quite a few brides come from out of state and plan this from afar.”

Pam Amodio, Director of Sales and Special Events, Essex Steam Train & Lady Katharine Cruises, has 35 years’ experience and is the mastermind behind the company’s concierge-style event planning.

“She is really skilled at knowing how to tailor each event to the right audience,” Maureen said of her co-worker. “She knows just what to offer the different brides who come in and works so closely and intimately with them to make sure that their event is perfect. From decorating the space to seating charts and menus, she just makes sure that each person who comes here has an extremely unique experience.”

With nearly 50 years’ in the train and riverboat business, Essex Steam Train & Riverboat looks toward a bright future creating one-of-a-kind memories for couples whether on their first date or setting a date for their nuptials. With the recent acquisition of Lady Katharine Riverboat, a luxury yacht experience out of Middletown, the team is always looking to add new events and excursions to their roster.

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