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A Vermont Christmas Train Ride On The Holiday Express!

Published: October 30, 2025

By: Adam Burns

All aboard the Okemo Valley Holiday Express, a beloved, family-friendly tradition that turns a classic Vermont Rail System excursion into a rolling celebration of the season. Set against the snow-dusted hills and historic towns of south-central Vermont, this festive train ride blends small-town charm, rail heritage, and holiday magic—an irresistible mix for families, railfans, and anyone who loves winter in New England.

What the Okemo Valley Holiday Express is

The Okemo Valley Holiday Express is a special seasonal excursion operated on the Vermont Rail System’s Green Mountain Railroad. Trains are decked out with cheerful decorations, holiday music fills the cars, and costumed characters help bring the spirit of the season to life. Expect Santa sightings, time for photos, and a cozy atmosphere where kids and grown-ups alike can sip hot cocoa, sing along to favorite tunes, and watch winter scenery glide by the windows.

While specific elements vary year to year, the vibe is consistent: it’s an immersive, nostalgia-rich outing designed to create lasting memories. Think twinkling lights, laughter in the aisles, and the gentle rhythm of steel wheels on rails as Vermont’s quintessential countryside rolls past.

Where and when it runs
Historically, the Holiday Express travels on the Green Mountain Railroad line through the Okemo Valley region. Most years, departures are scheduled on select dates between late November and December, often on weekends with multiple departures per day. Boarding has commonly taken place at a heritage station in the Okemo Valley (many riders will recognize the classic Chester Depot, a favorite for Green Mountain Railroad excursions), though exact boarding locations can change. Because details can vary by season, check the Vermont Rail System/Green Mountain Railroad and Okemo Valley regional event pages for the current year’s schedule, station address, and departure times.

The route itself delivers the kind of scenery people picture when they think “Vermont in winter”: forested hillsides, quiet villages, winding rivers, and historic track that once carried generations through the Green Mountains. The ride is typically about an hour, give or take, making it short enough for young kids yet substantial enough to feel like a true outing.

Who it’s perfect for
- Families with young children who want a low-stress, high-delight holiday activity
- Skiers and riders visiting Okemo Mountain Resort, looking to add off-slope fun to their weekend
- Rail enthusiasts keen on vintage equipment and historic lines
- Couples on a cozy winter getaway seeking something festive and photogenic
- Locals and second-home owners eager for a community tradition that supports the regional economy

What to expect onboard
- Festive atmosphere: Cars are decorated for the season, with holiday music and friendly staff creating a warm welcome from the moment you board.
- Santa and friends: Santa typically makes an appearance, meeting children, posing for photos, and spreading cheer car to car. Some years include additional characters or a light storytelling element.
- Snacks and sips: Hot cocoa and cookies are common touches. Offerings can change, so peek at current-season details before you go.
- Comfortable, heated cars: Green Mountain Railroad’s vintage coaches offer big windows and classic rail ambiance. Seating is usually assigned or general by car; either way, arrive early for the smoothest boarding.
- Photo opportunities: Between Santa, the historic equipment, and wintry scenery, there are ample reasons to keep your camera handy.
- Duration: Plan for roughly an hour round-trip, though timing varies slightly with schedule and operating conditions.

Tickets, timing, and tips
- Book early: Holiday trains are popular and often sell out. Buy tickets in advance through the Vermont Rail System/Green Mountain Railroad website or the Okemo Valley regional event listings linked from local tourism or chamber pages.
- Arrive ahead: Plan to be at the station 30–45 minutes before departure for parking, check-in, and stress-free boarding.
- Dress for the season: Cars are heated, but the platform and boarding process are outdoors. Hats, gloves, and winter boots make it more comfortable—especially for kids who want to explore a bit before boarding.
- Parking and directions: Station parking is usually free or included, but lots can fill close to departure. Follow signage and staff directions on arrival.
- Accessibility: Older stations and vintage cars can pose access challenges. If you or someone in your party uses a wheelchair or mobility device, contact the railroad ahead of time to confirm accommodations and boarding assistance for your chosen date and departure.
- Policies: Weather is part of the Vermont experience, and the railroad monitors conditions closely. Review the current season’s terms for refunds, exchanges, and weather-related contingencies.

Community roots and rail heritage
Part of the charm of the Holiday Express is its connection to Vermont’s rail story. The Green Mountain Railroad dates to the 1960s and is part of the family of short lines under the Vermont Rail System banner. These railroads keep essential freight moving year-round while preserving access to scenic, historic trackage that makes seasonal excursions possible.

The Okemo Valley itself is a winter destination anchored by Okemo Mountain Resort and dotted with classic Vermont towns like Ludlow and Chester. By hopping aboard the Holiday Express, riders do more than enjoy a memorable outing; they also help support a local network of small businesses—inns, restaurants, shops, and guides—that thrive when visitors linger for a weekend instead of a day.

Make a day (or weekend) of it
One of the best ways to experience the Holiday Express is to pair it with other seasonal favorites:

- Ski and ride: Spend a day at Okemo, then trade ski boots for snow boots and catch an evening train, or vice versa for families with early birds.
- Local shopping: Browse village shops for Vermont-made gifts—maple treats, artisan crafts, cozy knitwear—before or after your ride.
- Comfort food: Warm up at a local diner or farm-to-table restaurant. Winter menus often feature stews, roasts, and seasonal desserts.
- Lodging: Book a nearby inn, lodge, or vacation rental. A crackling fireplace after a holiday train ride is the stuff postcards are made of.
- Lights and cheer: Keep an eye out for town tree lightings, craft fairs, and community concerts that tend to cluster around the train’s operating dates.

Photography and memory-making tips
- Golden hour glow: If schedules allow, late-afternoon rides can deliver beautiful light. Night runs trade scenery for sparkle, with interior lights and festive décor popping in photos.
- Dress the part: Coordinating scarves, sweaters, or pajamas (a popular family tradition on holiday trains) make photos feel cohesive and fun.
- Capture candid moments: Some of the best shots are reactions—kids spotting Santa down the aisle, friends clinking cocoa, snowflakes catching on a coat sleeve at the platform.
- Ask staff: Train crews and hosts are accustomed to helping with quick snapshots. A polite ask usually gets you a friendly photographer.

Giving back
Many holiday train programs around New England incorporate charitable elements—food and toy drives, or partnerships with local nonprofits. The specifics for the Okemo Valley Holiday Express can vary. If supporting a cause is important to you, check the current year’s information for official donation opportunities or bring along a nonperishable item in case collections are happening at the station.

How to get the latest details
Dates, departure points, and onboard features can change from year to year. For the most accurate, up-to-date information, consult:
- Vermont Rail System / Green Mountain Railroad official website and event pages
- Okemo Valley regional tourism and chamber of commerce listings
- The event’s social media announcements during the season

If you can, sign up for email alerts so you’re first to know when tickets go on sale.

Why it’s worth your list
The Okemo Valley Holiday Express is more than a ride—it’s a shared moment that slows December down to the speed of a scenic train. It’s the glow on a child’s face when Santa says hello, the contented quiet after the carols, the clickety-clack that has lulled generations into happy reverie. Wrapped in Vermont’s timeless winter landscape, this is a tradition that feels both brand-new and wonderfully familiar every time you go.

All aboard—and happy holidays.