A small-town Christmas weekend to charm your socks off
Channel your inner Lorelei Gilmore: We’re going to Galena, Illinois, at Christmastime to stay in a late-1800s bed & breakfast, mingle with the 50+ crowd, and hope for snow. For my mom and me, this was our third trip to Galena in four years for their weekend of Living Windows and Luminaria.
That's when everyone in the hillside town bands together to light up the streets with Christmas lanterns — thousands of them! At the same time, the picture windows on Main Street come to life with sweet holiday scenes. We’ve slowly been fine-tuning our plans to find the perfect Galena itinerary. Here’s where we’re at after year three.
First, to get there before dusk, make sure to leave Milwaukee by 1pm or even noon. Adjust the timing depending on your starting point, of course. Might sound wimpy, but driving winding country roads during winter after sunset is actually quite nerve-wracking. For our most recent trip, we got a bit of a late start and ended up on pins and needles watching for deer — and we saw four, one of which was standing in the road.
We stayed at the Lamberson Guest House, which I can’t recommend enough. The woman who owns it is warm as can be. She remembered my mom and me from two years ago and greeted us with big hugs. If that’s not your thing, good news: Galena is on Airbnb! So you can have your space if that's what you crave. But know that then you can’t also have warm cinnamon scones and biscuits with sausage gravy and baked apples topped with oats and cinnamon. Sometimes, it's worth the mingling and the letting down of your personal barriers.
Lamberson also has a wine and cheese happy hour every day at 5pm, so arriving in time for that is a plus. The rooms themselves are impeccable and come complete with an electric fireplace, TV and DVD player (good for watching “White Christmas” before bed), and better soaps and such than you’d find at a hotel. Oh, and brownies wrapped in cellophane, perfect for a midnight snack.
This year, we made reservations at our favorite restaurant, Fritz & Frites, two nights in a row. Ideally we’d make a Friday night reservation for 6:00 or 6:15. That gives you ample time to eat, then come back and enjoy your lovely room and get a good night’s rest. After all, breakfast is served Saturday morning promptly at 8:30!
After breakfast on Saturday, shop Main Street from about 10am–1pm. Make sure to hit up The Grateful Gourmet and my new favorite boutique, Galena Apothecary. Once your tummy is rumbling mid-afternoon, check out Victory Café to see about grabbing a seat at the diner bar for a mug of coffee and a cup of soup. After that: nap time.
On Saturday night of Living Windows and Luminaria weekend, venture out to view the windows at about 6pm. Make a dinner reservation at Fritz and Frites for 8:00, stopping at One Eleven Main for black cherry mojitos beforehand. We’d been told they’re the best drink in town and they actually lived up to the hype.
That, or adjust your Saturday night timeline to ensure more time to see the luminaria. Some of this depends on weather. If it’s snowing and beautiful, you may want to be out in it for longer! If it’s frigid-cold, stay inside as long as possible.
Ending with a late dinner at Fritz and Frites ensures you will see the post-9pm carolers come through. This year, they came closer to 9:30, so get the schnitzel, sip some coffee, savor the apple strudel, and relax and wait for some sweet singing to cap off your weekend.
