The Perfect Fall Weekend Road Trip: Galena, Illinois and Dubuque, Iowa

If you are already planning a fall trip to Galena, Illinois, do not stop there. Dubuque, Iowa sits just twenty minutes across the river, and pairing the two towns turns a solid weekend into the perfect fall getaway. This is the full 2 day itinerary we followed in early October, from the drive out of Chicago through both towns and back home, with everywhere we stayed, ate, and stopped along the way. For the deeper dive on either stop, we also have a full Galena guide and a full Dubuque guide if you want more detail than this combined itinerary covers.

A quick note before we dive in: this trip was pre Tira, so you will not see him in any of these photos. But since dog friendly travel is central to everything we do, we went back and confirmed the pet policies for every stop below so you know exactly what to expect if you are bringing your own pup along. 🐾

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Where to Stay in Galena

Galena has several cozy inns, bed and breakfasts, and boutique hotels perfect for fall. We stayed at the Irish Cottage Inn & Suites and we highly recommend it. It is a peaceful, welcoming spot just minutes from downtown Galena. It offers comfortable rooms, a complimentary breakfast, an on site pub and restaurant, and relaxing amenities like an indoor pool, hot tub, and spa. There is also a short nature trail that winds through the property, and at night the grounds are beautifully lit, adding extra charm. Plus, they offer a complimentary shuttle service to Galena’s Main Street, making it easy to explore downtown without worrying about parking.

Fall books up fast around here, especially during peak leaf season, so it is worth locking in your spot early.

Want to see everything mapped out at once? Here is a quick look at lodging options around Galena.

Dog Friendly Accommodations

If you are traveling with your pup, these are good bets just outside Galena.

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Fall Road Trip from Chicago Itinerary

Day 1: Chicago to Galena

The Drive Out

We left Chicago around 1 to 2 PM and took U.S. 20, the Grant Memorial Highway, straight into fall. Rolling hills, colorful trees, and quiet countryside the entire way. If you love a scenic drive, this route alone is worth the trip.

Long Hollow Scenic Overlook

Our first stop was Long Hollow Scenic Overlook, just off U.S. 20 in Elizabeth, Illinois. It is a quick pull off with sweeping views of the rolling hills and farmland surrounding Galena, and a great excuse to stretch your legs before continuing on.

Depot Park

From there we stopped at Depot Park on the east side of the Galena River. It gave us our first glimpse of downtown Galena across the water, with the fall colors framing the historic skyline. It is a peaceful little stop and a nice way to ease into the town before you are surrounded by shops and traffic.

Horseshoe Mound Preserve at Sunset

We timed our next stop just right and caught sunset at Horseshoe Mound Preserve. The trail up is short and easy, leashed dogs are welcome 🐾, and the views over the Galena River Valley and the surrounding farmland are some of the best in the area, especially in golden hour light. If you can time your drive to catch sunset here, do it.

Check In

After Horseshoe Mound we checked into Irish Cottage Inn and Suites and got settled before heading back into town for dinner.

Dinner and Dessert in Town

We headed into downtown Galena for dinner, no reservation, just walked in. Seeing Main Street at night in early October is a completely different experience than during the day. Between the historic buildings, the string lights, and the Halloween window displays in nearly every shop, it has this dramatic, almost cinematic small town Halloween energy.

Worth noting: Galena also hosts an annual Halloween Parade and Festival on Main Street, put on by the Galena Area Chamber of Commerce. It typically runs in late October with floats, marching bands, and a street festival, and it draws a big crowd. If your fall trip lines up with it, it is worth planning around.

We ended up at Cannova’s Pizzeria for dinner, cozy and right on Main Street, then walked over to La Michoacana for dessert since it stays open late.

Back at the Hotel

Once we got back to Irish Cottage Inn and Suites, we took some time to walk the grounds before heading in for the night. They are beautifully lit up after dark, a nice quiet way to close out the first day.

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Day 2: Dubuque and Back to Galena

Breakfast and Checkout

Breakfast was included with our stay, so we grabbed that before checking out and heading across the river into Iowa.

Julien Dubuque Monument

Our first stop in Dubuque was the Julien Dubuque Monument, and it made for a great start to the morning. The monument sits on a bluff above the Mississippi River, and the lookout gives you sweeping views up and down the river valley. Going first thing in the morning meant fewer crowds and beautiful early light. Dogs on six foot leashes are allowed throughout Mines of Spain. 🐾

Fenelon Place Elevator

Next was the Fenelon Place Elevator, billed as the world’s shortest and steepest scenic railway. The ride only takes a couple of minutes, but the views from the top over downtown Dubuque, the Mississippi River, and on a clear day parts of Iowa, Illinois, and Wisconsin, are worth it on their own. Parking here is street only, so we started at the top, rode down, browsed the shops at the bottom, then rode back up. Cash only, and it runs daily from April 1 through November 30. It is listed as pet friendly 🐾, though the cars are small, so this works best for small to medium dogs.

Washington Park

From there we wandered over to Washington Park, a small historic block tucked into downtown Dubuque with a restored gazebo. It is a quiet spot to slow down for a few minutes between bigger stops, especially pretty once the trees turn.

Dubuque Welcome Sign

A quick two minute stop for a photo at the Dubuque welcome sign, an easy way to mark the moment you crossed into Iowa.

Dubuque Shot Tower

We made our way to the Shot Tower along the Mississippi Riverwalk. It was a little rainy when we visited, and that moody light only added to it. The tower was built in 1856 to manufacture lead shot and is one of the last surviving shot towers in the country. You cannot go inside, but the view of the river with the railroad bridge behind it is one of the more underrated photo spots in town.

Back to Galena for Coffee

From Dubuque we headed back across the river to Galena and stopped for coffee at Kaladi’s Coffee Bar. We sat for a bit before heading back out to walk around.

Dowling House

Next was the Dowling House, the oldest building in Galena, built in 1826 and now a museum. Worth the stop if you love old architecture or local history.

Downtown Galena Shops

We spent the rest of the afternoon walking Main Street, popping into shops, and taking in the Halloween decor one more time in daylight. Main Street is walkable with leashed dogs 🐾, and Tira has since joined us here and was even welcome inside some shops. Galena has over 125 boutique shops downtown, so plan for more time than you think you need here.

Grant Park

On our way to Belvedere Mansion we stopped at Grant Park, a quiet, well kept park with a gazebo, scenic bridges, and a view overlooking downtown Galena that is especially pretty with the fall colors filling in. We sat on one of the benches for a few minutes before continuing on. It would also make a great spot for a small picnic if you have the time.

Belvedere Mansion

Before heading home we made a quick stop at Belvedere Mansion, a 22 room Italianate mansion built in 1857. It is open for tours from mid May through mid November, and even a quick walk through the gardens is worth the stop if you are short on time.

Heading Home

From there it was back on U.S. 20 toward Chicago, and just like that, the perfect fall weekend was over.

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If You Have More Time

If you can stretch this into a longer weekend, here is what we would add:

• Ulysses S. Grant Home in Galena, the restored residence of the former president
• Thunder Bay Falls, a quiet, hidden waterfall just outside Galena, especially pretty when the surrounding foliage is at peak color
• Julien Trail hike in the Mines of Spain Recreation Area in Dubuque, over twenty miles of trails and some of the best fall foliage views in the region. Dogs are welcome on leash throughout the park. 🐾

Any one of these would round this out into a full, more relaxed weekend getaway rather than a tightly packed two days.

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Final Thoughts

Galena and Dubuque genuinely complement each other. Galena gives you cobblestone streets, boutique shopping, and that small town Halloween charm, while Dubuque adds dramatic river bluffs and views you simply cannot get on the Illinois side. If you are already planning a fall trip to one, do not skip the other. It is an easy pairing and one of our favorite fall road trips so far.

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