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Connecticut's Halloween Train Rides

Published: August 25, 2025

By: Adam Burns

As the leaves turn fiery hues of red, orange, and yellow, and the crisp autumn air sets in, there's no better time to indulge in spooky festivities. In Connecticut, one of the most exciting ways to celebrate Halloween is aboard a themed train ride.

These excursions offer a unique blend of haunting entertainment and scenic exploration, perfect for families, friends, and Halloween enthusiasts of all ages. There are currently two different events offered during the holiday by the Essex Steam Train. Let's take a closer look at these excursions.

Essex Steam Train & Riverboat

The Essex Steam Train & Riverboat offers a unique and nostalgic experience in the Connecticut River Valley, combining the charm of vintage train travel with scenic river exploration. Operated by the Valley Railroad Company, this attraction showcases the area's natural beauty and rich history.

Visitors begin their journey at the historic 1892 Essex Station in Essex, Connecticut. The experience features a meticulously restored steam locomotive that chugs through the picturesque countryside, offering passengers panoramic views of lush forests, quaint villages, and the serene Connecticut River. The train journey generally lasts around an hour, allowing passengers to step back in time and relish the sounds and sights characteristic of classic steam travel.

The excursion isn't limited to rail travel. At Deep River Station, passengers have the opportunity to board the Becky Thatcher, a Mississippi-style riverboat. This vessel cruises the Connecticut River, providing a serene vantage point of the diverse river ecosystem, including opportunities to spot local wildlife such as ospreys and bald eagles.

The Essex Steam Train experience is not just about sightseeing; it's a journey into the past. Both the train and the riverboat offer educational narration, sharing insights into the history, ecology, and importance of the region. Special seasonal events, such as the Fall Foliage Cruises or the North Pole Express during the holiday season, enhance the offerings, adding variety and attracting repeat visitors.

This attraction is particularly well-suited for families, history buffs, and nature enthusiasts. By combining rail and river travel, the Essex Steam Train creates a memorable adventure that captures the beauty and history of the Connecticut River Valley, making it a cherished destination in New England.

The Salem Express! Revenge of the Sanderson Sisters

Held only on September 6, 2025 "The Salem Express" train ride with a Halloween theme.  Get ready to be spellbound by Winifred, Sarah, and Mary Sanderson, portrayed by the talented Summer Orlando, Miranda Miranda, and Bonnie Petite. They'll weave enchanting tales of witches and folklore straight from Salem and captivate you with a performance that marks the true beginning of the Halloween season!

Before you hop on the train, join this mystical coven for a meet and greet, complete with vibrant photo ops. Don't miss out on seeing Summer Orlando, renowned as New England's top Winifred Sanderson live singing impersonator, as featured in Disney's "Hocus Pocus 2!"

Channel your inner movie character or show off your best Halloween attire! Remember, this magical event is popping up for just one day, so secure your tickets now! This is a parody performance with professional impersonators and is not affiliated with or endorsed by the Walt Disney Company.

Tracks Of Terror

The "Tracks of Terror" is a bit spookier experience for the holiday season.  Please visit the railroad's website for more information!

A Hauntingly Good Time Awaits

Whether you’re seeking gentle ghosts or terrifying thrills, Connecticut’s Halloween-themed train rides offer something for everyone. From family-oriented pumpkin patches to adults-only spooky soirées, these railroad events provide an ideal way to celebrate the season while enjoying the state's beautiful autumn scenery.

As you plan your haunted adventures, consider one of these unique train excursions for a Halloween experience to remember. With costumes, stories, and a little imagination, you're sure to make memories that last long after the last pumpkin has been carved. So grab your ticket, don your favorite costume, and all aboard for a hauntingly unforgettable ride through the heart of Connecticut.