It goes without saying there is no shortage of holiday events in Chicago, from bars adorned with floor-to-ceiling decorations to lights taking up an entire zoo—we mean there’s even a returning Little Nero’s-themed pizza pop-up inspired by Home Alone.
But don’t let Chicago hold you hostage this holiday season; there are so many fun things happening outside the city limits.
One of them is in historic downtown Long Grove, named one of the best Christmas towns in America. Every year, the town transforms into something that feels like a Hallmark movie: storefronts are decorated with festive displays, carolers hit the streets, and carriage rides are the main form of transportation.
Officially called Vintage Holidays, the annual event returns November 20 through December 24, 2026.
Vintage Holidays begins with Light Up Long Grove
The season opens Friday, November 20, with Light Up Long Grove from 5–8 p.m. Shops will stay open late, with decorated, tractor-pulled wagon rides, illuminated photo stations, and street activities running from 5–7:30 p.m.
At 7:30 p.m., the village will light its bridge and Christmas tree, followed by a performance from the Fred Astaire Dancers.
Consider it your cue to trade the usual evening plans for a little small-town Christmas magic.
Expect carriage rides, carolers, and visits from Santa
And if you can’t make it opening night, don’t worry.
Horse-drawn carriage rides are scheduled for select weekend dates from November 21 through December 20. Reservations cost $15 per seat, while children ages 5 and under can ride free on an adult’s lap.
Carolers will be performing around town on select dates in December, and Santa will make several appearances throughout the season. There’s a free Santa photo event at Covered Bridge Park on Saturday, November 28, from 11 a.m.–3 p.m., with no reservations required. Visits are first come, first served.
Save your receipts for a free holiday gift
Here’s also a reason to keep those shopping bags—and receipts—close: the village’s Sip, Shop and Dine promotion rewards visitors who spend $150 before tax and tip at historic downtown Long Grove shops and restaurants. Qualifying receipts must be dated November 20–December 24, 2026.
Bring them to the Visitors’ Center at 145 Old McHenry Road to redeem a gift. Listed options include campfire mugs, plaid scarves, holiday treats, tote bags, and ornaments. Gifts are available while supplies last, so redeeming early means a better selection.
