Hinsdale's Holiday Express Now Rolls on Thanksgiving Sunday, and the Rest of November Lines Up Behind It

When does Hinsdale's holiday season begin? Most calendars mark it with the Chamber's Christmas Walk on the first Friday of December. This year the Village's own train to the North Pole leaves five days earlier, on the Sunday of Thanksgiving weekend. Several other November events also point toward that weekend.

The Village of Hinsdale Parks and Recreation listing sets the Hinsdale Holiday Express for Sunday, November 29. Tickets are $55, and the trip is for Hinsdale residents only. Families ride the train from Hinsdale to the Two Brothers Roundhouse in Aurora. The Village lists special holiday guests, a meal, festive activities and family fun at the other end.

The same trip, on a different calendar

The Village has run this outing before. Its 2019 Fall/Winter Recreation Programs brochure describes a Holiday Express that left Hinsdale Train Station for "the North Pole," meaning the Aurora Train Station. Families then walked into the Roundhouse banquet room for a buffet, a visit with Santa, photos, entertainment and holiday crafts. The brochure added one line that families with small kids will remember:

"Children are encouraged to wear their pajamas."

How you got a seat back then is where the two versions differ most.

The 2019 process was slow. The lottery deadline was November 8 and the drawing was November 11. Nonresidents could register for open seats on November 18, and the brochure said no online registration was available. Seating was capped at 150 riders on the early train and 110 on the later one.

The 2026 version has twice as many departures, takes registration through the Village starting October 5, and runs on the last day of the Thanksgiving holiday weekend. It costs more per seat. The trip moved earlier in the season and got easier to book.

Why the windows are all three hours and forty minutes

All four 2026 slots last exactly 3 hours and 40 minutes. Two start an hour apart in the morning, at 9 and 10, and two start an hour apart around midday, at noon and 1. The Village says the times may change with the Metra schedule.

That matters because the Holiday Express runs on the regular commuter line. Metra's BNSF line page lists both Hinsdale and Aurora as stops on the line toward Aurora. Commuters who ride downtown every weekday will be heading the other way, west past the stations they usually leave behind, all the way to the end of the line.

If you booked a slot, the Village page is the place to check for timing updates before you head to the depot. The listing gives a time window for each trip and no separate meeting address.

What waits at the end of the line

The destination is a building with its own railroad history. Two Brothers describes its Roundhouse at 205 N. Broadway in downtown Aurora as sitting across from the Fox River and the Aurora Train Station. The space is a supper club and the home of the Two Brothers Artisan Spirits distillery. The company calls it the country's oldest limestone roundhouse, a short walk from RiverEdge Park and the train station.

The 2019 brochure called the venue America's Historic Roundhouse Restaurant. The name has changed but the limestone walls are the same, and a family can still step off the train and be inside within a few minutes.

The Roundhouse also shows up earlier in November. The Hinsdalean's roundup of holiday races lists the Tom-A-Hawk Turkey Trot 5K at 8 a.m. Saturday, November 21, in downtown Aurora. It starts in front of Jake's Bagels at 220 N. Broadway and finishes by crossing the Fox River on the pedestrian bridge. The awards ceremony and post-race celebration are at Two Brothers Roundhouse. Prices went up after October 31.

November, counted forward to the train

With the Holiday Express on November 29, the rest of the month works as a run-up to it. Here is how the confirmed dates fall from now on.

1. Saturday, November 7: Holiday balloon wreath workshop. The Community House at 415 W. Eighth St. lists a DIY Holiday Balloon Wreath with Flair & Décor session from 10:30 a.m. to noon. The cost is $32.
2. Sunday, November 8: Last day for Jingle Dash early pricing. RunSignup says prices for the Jingle Dash go up after 11:59 p.m. that night.
3. Sunday, November 15: HJWC Jingle Dash 5K. The Hinsdale Junior Woman's Club holds its fifth annual Jingle Dash 5K Family Run at 9 a.m. in Robbins Park, near Vine and Sixth streets. The race page lists the Robbins Park Parking Lot as the location.
4. Saturday, November 21: Tom-A-Hawk Turkey Trot in Aurora. This is the 8 a.m. 5K that ends with awards at the Roundhouse.
5. Thursday, November 26: Thanksgiving races nearby. La Grange Rotary's 26th annual Pilgrim Pie 5K Run/Walk starts at 8:30 a.m. at Lyons Township High School's north campus, 1045 W. Cossitt Ave. The Grove Express 5K starts at 8:30 a.m. from Main and Grove streets in Downers Grove.
6. Saturday, November 28: Donuts with Dads. Hinsdale Public Library's fall 2026 newsletter lists a family drop-in from 10 to 11 a.m.
7. Sunday, November 29: Hinsdale Holiday Express. Four trips to Aurora between 9 a.m. and 4:40 p.m.

The Jingle Dash is the one Hinsdale event in that stretch with a registration deadline still coming up. According to The Hinsdalean, it runs on a USATF-certified course, with photo ops with Buddy the Elf, swag bags and a merry market. Runners are encouraged to wear their most festive holiday gear. Registration is $45 for adults, $25 for ages 11 to 18 and $15 for ages 10 and under. Strollers are free, and proceeds fund grants for charities serving women and children. The deadline to guarantee a race T-shirt was November 1, so anyone signing up now should register for the race itself and not count on a shirt. Sign-up is on RunSignup.

With Donuts with Dads on Saturday morning and the train on Sunday, Thanksgiving weekend has two Hinsdale family events on back-to-back days.

Five days later, the Christmas Walk

On Friday, December 4, the Hinsdale Chamber of Commerce holds its 60th annual Christmas Walk downtown from 5 to 7 p.m. The evening includes Santa, Santa's Village, a tree-lighting ceremony, a holiday train and a carousel.

The Village's special holiday guests will already be waiting at the Roundhouse on November 29, the Sunday before the tree lighting. For families who booked a seat, the holiday season starts on the Metra platform at the Hinsdale depot.

At Second City Agents, we keep track of Hinsdale's calendar the way our neighbors do, from the depot in Hinsdale to the end of the BNSF line in Aurora. If the Holiday Express gets your family talking about what the next few years in Hinsdale could look like, schedule a free market consultation and we'll go over it together.