Sometimes we only have a weekend to spare in the middle of our packed schedules, but that doesn’t mean we can’t go exploring. Our Day-Tripper Series packs a journey into the span of a weekend with niche locations around the United States. This weekend, we’re going to … 

Galena, Illinois

Ninety minutes north of the Quad Cities and a scenic three-hour drive from Chicago sits a town that looks like it fell out of a European postcard and landed in the hills of northwest Illinois. With 85% of its buildings sitting inside a historic district, Galena packs a full weekend of charm into a walkable little grid — here’s how to spend it.

1. Wander Main Street’s 1850s storefronts.

Galena’s Main Street is lined with well-preserved brick buildings from the Civil War era, now home to independent boutiques, galleries, and cafes — no chain stores in sight. Start with a stop at Galena River Wine & Cheese for a picnic-ready spread, then pop into Root Beer Revelry for a tasting flight the whole family can enjoy.

2. Sip something local.

Galena punches above its weight for wine and spirits. Take a tour and tasting at Blaum Bros. Distilling Co., a family-run craft distillery in the heart of downtown, or head just outside town to Fergedaboudit Vineyard & Winery for a glass with a view.

3. Take a walk with the goats.

Hoof It Goat Treks leads guided strolls through the forests and prairies just outside town, goats included — a genuinely odd but delightful way to spend an hour. Wine and root beer tasting versions of the trek run on select dates throughout the season, so check the calendar before you go.

Wherever your Galena weekend takes you, pin your Main Street stops, tasting rooms, and trailheads right in the ALLMYNE app before you set out — so you’re spending your time exploring the town instead of hunting for directions between stops.