Source: Main Street, Galena

Take a Holiday Getaway in Galena, Illinois


The small city of Galena, Illinois, one of the Midwest's best spots for a late fall or early winter escape, is properly pronounced with a short "a" sound: Guh-leena.

But it'd be understandable if you mistakenly called it Gay-leena.

After all, with a gorgeous rural setting, queer-owned businesses, splurge-worthy holiday shopping, and all around adorability, Galena has long been a favorite romantic getaway for LGBTQ+ couples from across the state and beyond.

Within easy driving distance of Chicago, Madison, WI and Cedar Rapids, IA, Galena turns up its natural charm even further every December, decking itself out in twinkling holiday lights all month long. Midwest Life magazine named Galena the region's Best Holiday Town.

The Inn at Irish Hollow
Source: Illinois Office of Tourism

Holiday Celebrations

The Galena Center for the Arts' "Wonder of Winter" art show runs into January. The Trolley Depot Coffee & Tea Company offers hands-on seminars on brewing the best winter warm-ups, complete with a specially curated dessert plate for all participants.

Welcoming Accommodations

One of Galena's most appealing places to stay is the Aldrich Guest House, run by husbands Robert and Douglas Mahan. While the landmark inn has played host to past Presidents, Ulysses S. Grant, and Abraham Lincoln, its current claim to fame is being Illinois' first and only cannabis-friendly bed and breakfast, with a dedicated "Potting Shed" and a patio for outdoor indulgence.

Another enticing gay-owned option is The Inn at Irish Hollow, set on a 500-acre working farm in the countryside. Innkeepers Bill Barrick and Tony Kemp estimate that 50% or more of their guests are queer. In addition to rooms in the main building, couples often arrange to stay in private cottages on the grounds to enjoy ultimate privacy. The gentle rolling hills here are ideal for cross-country skiing and snowshoeing.

by Jim Gladstone

Jim Gladstone is a San Francisco-based writer and creative strategist.

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