Our senior designer returns to her hometown each October for dining, shopping, hiking, biking and more. Here’s what she recommends.

I grew up in Galena, and my family still lives there. There's something about the chill in the air and changing of the leaves that has me longing for home every time October hits. Growing up, the change of season kicked off with a caramel apple, followed by my neighbors transforming hay bales into Halloween decorations, the community volunteering at the Country Fair, and marching in the annual Halloween parade. My visit during the pandemic was much different, but it made me appreciate the things we could do together, like take sunny bike rides, make impromptu roadside stops and cook salted caramel apple skillet cake at home.

Galena, Illinois
Great American Popcorn Co.
| Credit: Erin Keeffer

Dining Guide


I like Otto's Place,in a historic building across from the Old Train Depot. Sip your coffee in the second-floor lounge while waiting for a table. Always order the coffee cake or a cinnamon roll—I call it a breakfast appetizer. Follow with the daily quiche or sweet potato hash.

Fall Snack

Apple cider doughnuts, hands-down. If you are strolling downtown, go to Galena Canning Company. For more of an adventure, head to Orchard Landing Apple Farm.

Lunch or Dinner

If you have time to sit down for lunch, try Embe's downtown. My go-to order is a cup of the housemade cream of mushroom soup with artichokes and sun-dried tomatoes and the Embe salad with their signature vanilla bean balsamic. Do NOT skip the bread pudding dessert!

For a quick grab and go, stop by Galena River Wine and Cheese to get a custom grilled cheese. Choose any cheese in their cabinet and accent with delicious add-ons. How about a French Brie grilled cheese with apple horseradish jam?

Galena, Illinois
Horseshoe Mound
| Credit: Erin Keeffer

Outdoor Adventure

Take a sunrise hike at Horseshoe Mound. Many people come for sunset, which is the best view, but I find it more peaceful in the morning. After your hike, park your car at the city's free public parking lot on the east side of the river near the Old Train Depot, and take some time to explore the area.

Two trails lead out from the parking lot. Head to Buehler Preserve for a shorter bike ride or walk (2 miles out and back) or take the 8-mile Galena Bike Trail for a longer trek. For great views, head up to Grant's Home and stroll down Park Avenue.

Galena, Illinois
Galena Apothecary
| Credit: Erin Keeffer


I love strolling through downtown Galena to pick up a few goodies. Some of my favorite stores:

Opened in 2020, Galena Book and Paper has an incredible selection of books and stationery products. If you are like me, the pandemic has made you more of a reader. I've been building my library with great finds from this shop. Stay a while to browse, admire the adorable fireplace, and take in that crisp bookstore scent.

Beauty products, home goods, jewelry, antiques, artwork, candles—you can find it at Galena Apothecary. My fall vote is for a new cozy candle.

For everyone who likes to cook (or eat), the Grateful Gourmet is the stop. I almost always come here to stock up on Galena Roasters Coffee, roasted by the owners. P.S. If you want to try before you purchase, check out their coffee shop down the street.

Galena, Illinois
Mums in Woodbine
| Credit: Erin Keeffer

Beyond Galena

My family lives east of Galena, and the scenic drive on Highway 20 to visit them reminds me of how much I love the Driftless region, with its gentle rolling hills. My favorite towns to drive through are Elizabeth, Woodbine and Stockton. On the drive, you can stop at the Long Hollow scenic overlook and Terrapin Orchards. Keep an eye out for roadside pop-ups with mums, pumpkins and other fall treasures. If you really want to wander, turn off Highway 20 onto a county road that takes you through little towns like Apple River, Shattville, Massbach and Scales Mound.

Next Time

I'll visit the Galena Bakehouse, created by former innkeepers of The Inn at Felt Manor. I've been drooling over the artful pastries on their Instagram feed, and I am excited to go to Bakehouse and try them out!

I am also looking forward to the Twenty Dirty Hands self-guided pottery studio tour, celebrating its 21st anniversary in 2022. Scheduled for the third weekend of October, during prime leaf-changing season, the tour through Northwest Illinois combines beautiful fall landscapes and art into one weekend. The tour also has expanded this year to include studios in Asbury and Maquoketa, Iowa.