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Destinations & Day Trips

Adults Only: Sunset Cigar and Whiskey Cruise

Essex Steam Train Whiskey & Cigar Cruise
Written by Timothy Stobierski

Okay, we all know that smoking and drinking are bad for you, but sometimes you’ve gotta unwind. The Essex Steam Train has got you covered.

Yes, we all know that smoking and drinking are bad for you. But while we wouldn’t recommend you make either a habit, sometimes you just want to unwind with a nice cigar and glass of whiskey. (No judgment from us: We’ve been known to indulge ourselves from time to time.)

If the above paragraph has piqued your curiosity and made your mouth start to water in anticipation of that whiskey, you may be just who the Valley Railroad Company had in mind when they decided to create the Sunset Cigar and Whiskey Cruise.

Did You Just Say “Cigar and Whiskey Cruise”?

As odd as that may sound, yes, that’s exactly what we just said. On May 25, passengers will board the Essex Steam Train for the half hour journey to the Becky Thatcher Riverboat. Once there, guests will join other cigar and whiskey enthusiasts for a 90-minute cruise featuring, you guessed it, cigars and whiskey.

But the cruise is more than just an excuse to drink whiskey and smoke cigars. Designed to be an experience like no other, guests will taste three whiskeys specifically chosen for how well they pair with cigars. The featured whiskeys are Knob Creek, Wild Turkey Forgiven, and Crown Royal, in case you’re curious, and other spirits will also be available for purchasing if you’d like a bit more (including Tullamore Dew, Jameson, Jack Daniels, and Jim Beam).

The cigars provided are hand-rolled and Connecticut-wrapped by Up in Smoke, a premium cigar store and lounge in Cromwell. Up in Smoke will also be demonstrating the art of cigar-rolling throughout the cruise so that guests walk away with a deeper understanding of what it takes to roll the perfect cigar.

In addition to enjoying the smoke and libations, there will also be a range of foods to nibble on throughout the event, from a table of Tuscan meats, cheeses, and dips to both hot and cold appetizers including potato pancakes with dill crème fraiche and smoked salmon on toast. If you’re especially hungry, there is a pasta bar serving pasta (duh) with meatballs and classic red and white sauces.

cigar and whiskey cruise

Photo by Christopher Smith.

Who is Becky Thatcher Anyway?

You may be wondering who this Becky Thatcher is and why they named a riverboat after her. It turns out, there’s a good reason that the name sounds so familiar: She was the love interest of Tom Sawyer in Mark Twain’s best-selling books.

According to Paul Costello, who works onsite with the train and riverboat, the Mark Twain connection to the riverboat actually spurred the idea of a cigar cruise to begin with. Since Mark twain was a known lover of cigars, and the Becky Thatcher was named after a Mark Twain character and resembled a Mississippi riverboat, the connection just “made sense.” In honor of Twain, who liked to smoke Churchill cigars, the cigars being provided are Churchills wrapped in Connecticut tobacco leaves.

The Only Steam Train and Riverboat Connection in the Country

The Valley Railroad Company, operating the Essex Steam Train & Riverboat, has been serving the lower Connecticut River Valley since 1971. They operate with a mission to keep alive the rich mechanical, industrial, and transportation heritage of our state through the ongoing operation of vintage steam and diesel locomotives, passenger coaches, and the facilities and infrastructure to support these.

What’s more, this is the only steam train/riverboat connection in the country. Any trip is bound to be memorable and one of a kind. If you’re a fan of trains and would like to relive a bit of their glamorous history, be sure to also check out the Essex Clipper Dinner Train, with its four course meal offering. But check it out soon, because seats sell out fast.

If You Want to Go

If you’re interested in going, the cruise costs $75 with advance ticket purchase or $85 at the door (if tickets are still available). The train leaves the Essex Station at 6:30pm on Thursday May 25, and the Riverboat Cruise will take place from 7 to 8:30pm. You’ll arrive back at the Essex station at 9pm. In case you need it, the Essex Station is located at 1 Railroad Ave in Essex.

The ticket price includes the train ride and cruise, a hand-rolled, Connecticut-wrapped cigar, half-ounce tastings of the featured whiskeys, various foods, a gift bag, and a souvenir glass. The event is limited to those 21 years and older.

About the author

Timothy Stobierski

Tim Stobierski is a Connecticut native and a freelance writer and editor who has worked with a number of publishers including Taunton, Abrams, and Yale University Press. He has written for Grow Magazine, The Huffington Post, The Hartford Courant, and many other publications. His first book of poetry, Chronicles of a Bee Whisperer was published in 2012 by River Otter Press. He is the founding editor of, a website focused on helping college students avoid and pay off their student loan debt.

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