Water Bottles and Wine Glasses: A Girls’ Weekend in Galena

Last Updated on August 5, 2025

A group of friends and I recently planned a girls’ weekend in Galena, Illinois. Outdoor adventure mixed with shopping and good food made Galena a great fit for our girlfriend getaway.

Located in northwest Illinois, Galena is right near the Wisconsin and the Iowa borders. Rolling hills and flowing rivers beside a lively and charming historic town created a great setting for us to kick back and have some fun.

The town is home to 3,000 residents, but nearly 1 million people visit Galena every year. It’s no surprise Galena is a popular vacation destination: the city is less than a 3-hour drive from Milwaukee and Chicago; more than 85% of the town is on the National Register of Historic Places; and it’s located on the Mississippi River next to hills, valleys, trails, and bluffs – perfect for nature excursions!

(Browse Galena lodging options here: Galena accommodations)

If you’re like us – filling your water bottle in the morning before an active adventure, then happily trading that water bottle for a wine glass in the evening – read on. Our girls’ weekend in Galena provided a nice mix of activity and relaxation, offering a chance to hike, kayak, shop, wine and dine.

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Hiking Near Galena

Apple River Canyon State Park

Driving to Galena from the east, we began our trip with a stop at Apple River Canyon State Park – 26 miles east of Galena. We each brought a bag lunch to eat before we set out hiking and we immediately found one of the park’s four picnic areas with tables, a shelter, and toilets nearby.

Apple River Canyon State Park is free to enter and has five hiking trails. There are easy, moderate, and rugged paths, ranging in distance from ¾-mile to 1.5 miles round trip. You’ll wind your way up and down dirt hills, through trees, to scenic canyon overlooks and to the base of the Apple River.

Some of the trails overlook deep ravines, so you’ll want to be careful and stay on the trail. These hikes were short but doing a few of them together gave us a pretty good workout and was a nice way to start our vacation.

Chestnut Mountain

Later in our trip we spent a couple hours exploring and hiking around Chestnut Mountain Resort – 9 miles south of Galena. We weren’t staying at the resort, but the trails and amenities are open to the public. While they offer mountain bike rentals, we decided just to hike the trails. We were a little surprised that the trails were so short. They did lead to some scenic views of the Mississippi River, but we were glad we didn’t spend the money to rent bikes. It really isn’t the best hiking or biking destination.

The resort offers other outdoor activities, too. The disc golf course was very popular the day we visited, and they have an alpine slide that careens down the mountain to the banks of the Mississippi for $10/ride.

The on-site restaurant, Summit Bar and Grill, was a nice way to end our time at Chestnut Mountain. They offer a wide variety of salads, sandwiches, and wraps which we enjoyed out on their large deck overlooking their beautiful property.

Galena River Trail

The Galena River Trail is just minutes from downtown and is another option for hiking or biking in and around Galena. The trail is a flat, crushed limestone path stretching for 8 miles along the Galena River. You can rent electric bikes in town to use on the trail or simply stroll along seeing the sights. We opted not to hike this trail because we had kayaked down the Galena River and saw much of the sights that way.

Kayaking the Galena River

Kayaking was an interesting adventure during our girls’ trip to Galena. With a chance of cold temperatures and rain that morning, we didn’t know what to expect. But we ended up having a beautiful sunny, blue-sky day as we paddled down the river.

We rented kayaks through Nuts Outdoors in downtown Galena. They provided transportation to a spot up the Galena River and helped us into the water. Then we kayaked on our own down the river to a spot where they met us to collect the kayaks.

The employees didn’t offer any instructions (other than where to meet) which made some of our beginner kayakers apprehensive. But besides that, and some small rapids which drifted our kayaks into the riverbank (sometimes turning our kayaks backwards!) we didn’t encounter anything we couldn’t handle.

The water level was very low which was a good thing for those in our group afraid of falling in, but bad for super smooth sailing. A couple of us got stuck on sandbars and had to work to get free. All in all, it was a fun adventure that kept us on our toes.

(Like to kayak among beautiful scenery? Check out these other Midwest kayaking destinations: Apostle Islands, Door County, Starved Rock.)

Shopping on Main Street

Galena is the quintessential location for a girls’ weekend – and Main Street is a major reason why. More than 125 independently owned shops, wineries, and restaurants line the street.

Voted one of America’s Best Main Streets by Fodor’s Travel, Galena’s Main Street exudes so much charm along every storefront. Housed in historic 19^th century buildings, these unique boutiques kept us browsing for hours.

You’ll find a mix of clothing, antiques, jewelry, home décor, candy, popcorn, spices, gifts, and collectibles. We were there in the late afternoon and evening and noticed some stores closed 1-2 hours earlier than others. So be sure to make note of which stores you really want to visit and check their hours so you don’t miss out.

(Another Midwest destination known for cute shops, wineries and natural beauty is Door County, Wisconsin. Click here to read all about it!)

Time for a Wine Break

Sprinkled among the stores are several wineries – the perfect shopping break if you ask me. Sipping on wine from Galena Cellars Winery, we sat at one of their outdoor tables along the street. Tasting a variety of wines while people-watching and chatting with friends as the sun went down made for a great evening on our girls’ getaway.

If wine’s not your thing, there’s also a brewery, distillery and coffee bar nearby.

Galena restaurants

Choosing where to eat during your girls’ weekend in Galena may be harder than you think. With a variety of casual and upscale Galena restaurants to pick from, you can opt for Mexican, Asian, Irish and Italian cuisine, among others.

We went with a local favorite – Fried Green Tomatoes. We had read good reviews about this place and we were not disappointed. They offered up a delicious variety of seafood and pasta dishes – and of course their fried green tomato appetizer. I highly recommend trying their namesake specialty.

Another Galena restaurant we ate at was the Galena Brewing Company. They have 13 craft beers on tap with a selection of seasonal brews. You can order one or sample a flight as you dine in this fun, casual location. They serve more than traditional pub food, too, with dishes like vegan crab and kimchi, portobello croissant, and lamb gyro on the menu.

If your group of friends likes their water bottles and their wine glasses, plan a girls’ weekend in Galena, Illinois. Then come back and tell us all about it in the comments. We’d love to hear from you!