There is a version of the Minneapolis holiday-lights date that everybody has already had. You drive around in your own car with the heater on full, someone navigates badly, you argue mildly about which street had the good house, and you are home by nine.

Here is the better version, and it starts indoors.

Start with a drink in a hundred-year-old mansion

Every Holiday Light Ride boards at the Pillsbury Club — the Charles S. Pillsbury Mansion at 100 East 22nd Street, an English manor finished in 1916 and on the National Register. That is the part that turns a light tour into an evening.

Come early. The bar pours handcrafted seasonal cocktails, the dining room is open for dinner or something small before you board, and the house is decorated. You are having a drink in a room panelled in centuries-old English oak, in front of fireplaces that crossed the Atlantic. Most guests tell us this hour becomes their favourite part of the night — which is a slightly awkward thing for a trolley company to admit, but it is true.

Then pick your ride: Naughty or Nice

There are two, and for a date the difference matters.

The NAUGHTY Holiday Party Ride is the adults-only one — 21+, roughly two hours, billed as part lights tour and part rolling holiday party. Christmas music, festive lighting, other adults out celebrating. This is the date-night ride, and it is also the girls’-night and the office-party ride, so book it as far ahead as you can stand.

Santa’s NICE Ride is the family-friendly hour — narration, Christmas music, and a vote for the best-decorated house along the way. It is the right pick if the date includes grandparents, or children, or anyone who would rather not be on a party bus. It is also, quietly, a lovely low-key first date.

Both run on a heated vintage trolley, which is the whole trick. December in Minneapolis is not a season for open-air anything; the National Weather Service Twin Cities office will tell you what you are walking out into, and the answer between Thanksgiving and New Year is usually “wear the coat.” On board, you do not need it.

Why boarding at a mansion beats boarding at a parking lot

The competing holiday-lights trolleys in this market check you in outside a bar or in a parking lot. That is a functional arrangement and nothing more: you stand around in the cold with a cooler, you get on, you get off, you go home.

Boarding here means the evening has a beginning and an end that are not “the car park.” Before the ride there is a bar, a dinner menu, a holiday market of Minnesota makers, and a house worth walking around. Afterward, the same. It is the difference between an activity and a night out.

And the parking, since somebody always asks: it is free, across the street.

Make it a longer evening

If you want more than the ride, the mansion supports it. Guided tours run year round — details on Experiences and Tours — and if the date is really a small group, the private club rooms can hold it, including the Emerald Suite for up to ten. We wrote about booking a private room for a small group separately.

History buffs on a date have it easy here: the fireplaces, the oak and the ancient glass all have stories, and we tell them properly over in the History Journal. The Minnesota Historical Society is the place to go deeper on the milling families who built this stretch of Minneapolis.

Practical notes before you book

Rides run through December and the popular slots go first — weekend evenings closest to Christmas sell out earliest, and the 21+ ride goes before the family one. Hours, policies and directions are on Plan Your Visit. If you would rather not drive at all, Metro Transit’s Trip Planner will get you to 22nd Street.

Ready to book the date? Ride dates and tickets are on the Holiday Light Ride page — pick Naughty or Nice, then come early for a cocktail.

Keep reading: What Was the Costessey Collection, and How Did Its Stained Glass Reach Minneapolis?