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Connecticut's Whiskey Train Rides

Published: July 9, 2025

By: Adam Burns

Connecticut, a state known for its picturesque landscapes and rich history, offers a unique blend of experiences for both locals and tourists alike. Among the delightful experiences this New England state has to offer are whiskey/bourbon tastings by train, at two different locations!

These rides are a perfect amalgamation of scenic beauty, historical charm, and fine spirits, offering passengers an unforgettable journey. In this article, we'll take a closer look at these special train rides, explore the magic behind them, and offer tips for anyone looking to embark on this memorable journey.

The Charm of the Rails: A Historical Perspective

The story of train travel in Connecticut can be traced back to the early 19th century when the Hartford & New Haven - first chartered in 1833 - opened its initial 36 miles between its namesake cities in 1839.  This system would later become the New York, New Haven & Hartford that served all of southern New England and was an important transportation artery for generations.

The golden age of railroads left a lasting impression with tracks crisscrossing the verdant landscapes. While passenger rail service was once the most popular mode of long-distance travel, it has been reimagined today to provide unique experiences tailored to niche interests—such as whiskey tasting.

The Whiskey Train Experience

These unique excursions for those 21 years or older offers a captivating experience, blending fine spirits with a relaxing train ride. 

What to Expect

Comfortable Passenger Cars: The restored rail cars are designed to offer a cozy and nostalgic experience, complete with plush seating and usually climate controlled.

Culinary Pairings: In addition to whiskey, guests are treated to perfectly paired light bites or more substantial menu options, crafted to enhance the tasting experience.

Live Entertainment: Many of these rides feature live music or storytelling, adding an extra layer of enjoyment to the journey.

Notable Locations

There are currently two locations in Connecticut offering special excursions that includes either whiskey or bourbon tasting, the Essex Steam Train and Naugatuck Railroad.

Essex Steam Train & Riverboat

Known for its beautiful steam engines and charming routes, the Essex Steam Train offers occasional themed rides, including whiskey tasting excursions. Passengers enjoy scenic views along the Connecticut River, making this one of the more picturesque experiences.

In 2024 the railroad hosted their "Cigar & Whiskey Cruise", which included a train ride from the Essex Station to the Deep River Landing where guests boarded the Becky Thatcher riverboat to enjoy fine spirits, cigars, appetizers, and live music.   As part of the experience guests could take home an official Essex Steam Train & Riverboat rocks glass.

Naugatuck Railroad

This line, operated by the Railroad Museum of New England, occasionally offers specialty train rides. While traditionally known for their foliage and holiday trains, whiskey events are periodically scheduled, attracting whiskey aficionados.

On select dates the railroad hosts the "BBQ & Bourbon Special" which includes a roughly 3 hour excursion with the meal provided by Mission BBQ of Southington and bourbon/whiskey from the Bad Dog Brewing Company.  The railroad states there are four whiskey/bourbon tastings offered.

A whiskey by train is more than just a journey; it's an experience that invokes a sense of nostalgia, adventure, and indulgence. Combining the allure of train travel with the sophisticated pleasure of whiskey tasting, these rides offer a unique way to explore the state's stunning landscapes and savor its spirits.

Whether you're a whiskey connoisseur or simply looking for an exceptional escapade, hopping aboard a whiskey train is an experience sure to leave a lasting impression.

Embark on this one-of-a-kind journey, and let each sip of whiskey and every click of the train tracks transport you to a place where time slows down, and the simple joys of life and travel are celebrated.