A Romantic Holiday Weekend Escape to Stillwater

With Victorian carolers, a picturesque Main Street and festive events (holiday tea!), this wonderland outside of the Twin Cities is ideal for a quick getaway.

By

Jess Hoffert

Updated on November 20, 2023

Stillwater Minnesota in winter — Photo: John Noltner

All summer long, the Stillwater Lift Bridge dutifully rises and falls to let sailboats and gondolas drift past below. But in December, the vast span sits still, quietly aglow with a gleaming string of white lights. Stretching over the St. Croix River between Minnesota and Wisconsin, the bridge anchors a town that's sometimes called the birthplace of Minnesota. (The journey to statehood began at a territorial convention here in 1848.) Today, the Twin Cities' sprawl creeps right up to Stillwater, but with its picturesque Main Street nestled among river bluffs, the town feels farther away—the perfect recipe for a quick winter escape.

On weekends during the holiday season, Victorian carolers, live reindeer and a roaming Santa pepper a five-block stretch of cheerfully decorated shops and restaurants. You might hear some tipsy amateur singers, too, pedaling past on a bicycle built for 13, thanks to Biercycle Caroling Tours. Take a spin—you're sure to make a few new besties—or if that doesn't jingle your bells, slip into The Tilted Tiki for "Mele Kalikimaka" vibes.

When you've had your fill of merriment, retreat to Lora, a boutique hotel downtown that sits on the foundation of the 1868 Joseph Wolf Brewery. Architects retained funky details like exposed stone walls and mysterious cave entrances—and, conveniently, the hotel is right next to one of Stillwater's five historic outdoor staircases. So before you snuggle up by your in-room fireplace, take a heart-pounding 100-step climb up the bluff for a sweeping postcard scene: rooftops, steeples, the wide St. Croix River and the iconic lift bridge, shining through the night.

The Nice List

Shop

Trim the tree with handcrafted European ornaments from the only Käthe Wohlfahrt shop in the United States. Score regionally made treasures at Smith + Trade Mercantile. Stock up on mint-chocolate malted milk balls at Candyland.

Drink

Wake up to espresso and fresh-pressed juices at Made Coffee within Lora hotel. At night, head underground for classic and contemporary cocktails at The Velveteen Speakeasy.