Living in Chicago, there are so many fun weekend getaway spots, and I love exploring them. One of my favorites is straight west of here, and I love finding new fun things to do in Galena Illinois.
Note: I was not paid to write this article, nor did I receive complimentary tickets from these places except where noted. This list is compiled from my visits to Galena and experiences I had either with friends or with family.
Galena is on the Iowa border with Illinois, on the Mississippi, and it has different topography from much of Illinois, which means there are even more things to do. You find it in northern Illinois in Jo Daviess County, near Dubuque, Iowa.
No matter what you enjoy, there are activities sure to please both young and old. I’ve visited Galena with friends, with my kids and without, and with friends who have a very young kid as well as my teens.
Galena has a ton of history to it that they celebrate, yet they are not stuck in the past with nothing but museums for those who enjoy other activities.
While some activities are only available during the summer months, Galena celebrates winter activities, too, which makes it a great spot to visit year round.
Fun Things to Do in Galena Illinois
Galena Trolly Tours
If you’ve never traveled to Galena, or even if you have, the Galena Trolly Tours are a fun way to spend an hour to learn about the town.
You can find them right on the main drag in downtown Galena at 314 South Main Street.
The tours run seven days a week from May to October, and they have weekend tours in March, April, November, and December with varying hours. In season, tours run starting at 10am with the last tour leaving at 4pm daily.
The trolleys are open air but have windows that close to heat them in cooler (or wetter) weather. The wooden seats are fairly comfortable, especially since it’s just an hour.
The tours take you not just throughout the main downtown area but throughout Galena to learn about the history of the town and its evolution over time. The narrators are filled with information and tidbits you won’t find elsewhere.
They offer multiple tours a day, so if the first tour you want to take is sold out, grab a ticket for the next one and hang out in the coffee shop and cafe next door while you wait.
The tickets are $20 plus tax per person (ages 13+) for the one hour tour. Kids five and under are free, while those 6-12 are $9 plus tax each.
As fun as the overall tour of Galena is, I love some of the more unique tours available. Galena actually offers ghost tours, though not every evening.
With so much history in the area, it is no surprise that there are multiple companies offering different styles of ghost tours in Galena.
Haunted Galena Ghost Walk
Haunted Galena Ghost Walk provides tours Wednesdays through Sundays starting at the end of April through late October. Each tour for those ages 7 and above lasts for 90 minutes and costs $23.50 per person.
Meet for this tour at the Dowling House (see more below), which is downtown at 220 Diagonal Street. Note that the tour ends at the DeSoto Hotel, which is also downtown but not the same location.
These tours are all walking, so come dressed for the weather with comfortable shoes. They postpone tours for severe weather, but expect to enjoy them rain or shine in general.
This tour focuses on mostly historical story-telling versus ghost hunting, though you may bring equipment if you wish so long as it doesn’t interfere with the tour itself.
For a more lighthearted version, Haunted Galena Ghost Tours also offers a haunted happy hour year round on Saturdays at 4pm. This one requires you be 21+ to join.
Over 90 minutes, you visit three haunted establishments where you enjoy a specialty drink at each while hearing the stories. For $30 per person, you can’t beat this fun way to start your Saturday night.
Amelia’s Galena Ghost Tours
Amelia’s Galena Ghost Tours does their ghost tour via shuttle bus if you prefer to avoid walking tours. You have your choice of 6pm, 7:30pm and 9pm seven days a week, year round.
All tours leave from their theater at 129 South Main Street in downtown Galena.
This tour visits an 1800s cemetery as well as the Ryan mansion where you learn to use ghost hunting tools in addition to listening to ghost stories and history on this 75 minute tour. This tour costs $32 per person.
Matthew’s Haunted Pub Crawl
Matthew’s Haunted Pub Crawl is not the debauchery its name inspires. While this 2 1/2 hour walking pub tour does visit two to three different locations, you are not required to imbibe.
At each location – which varies by tour – you learn about Galena specific ghost stories, and you have the opportunity to use ghost hunting equipment at each pub you visit. Matthew is the guide for each tour, and he is a bundle of energy and enthusiasm.
The tours run at 8pm each night year round, but check the schedule for periodic days off. Tours cost $32.18 per person and require that you book at least two adults (21+ only) when you book.
This is a walking tour with about five minutes walking between each location and operates rain or shine, so come dressed for the weather. He’ll let you know where to meet (downtown) once you’ve booked.
Hot Air Balloon Ride
Without question, a hot air balloon ride is a splurge, but it is one of the most fun things to do in Galena Illinois, hands down.
I took a hot air balloon trip with Galena on the Fly on my first trip to Galena, and I will never forget it. They offer both sunrise and sunset balloon rides, so choose your time of day.
The ride costs $250 per person if you pay cash and $260 per person if you use a credit card. They will hold your credit card even if you intend to pay cash, as a heads up. And yes, you need to bring your physical card to the ride for them to process it on site.
You can also book a private balloon ride for $3200 or Monday through Friday mornings, you can book a private flight for two people for $1200.
For the hot air balloon ride in Galena, you leave from Eagle Ridge Resort and Spa. Park there, and you will get a ride back to your car at the end of the trip.
I am not a morning person, but I took a sunrise balloon ride, and it was breathtaking. I was a bit concerned about being in an open basket before the ride, but once you get in and see how secure you are and how smooth the ride is, you forget all your worries.
Focus on the awe instead.
The balloons hold 14 people, and you have plenty of room without feeling crowded though it is cozy. Recognize that it is chilly at 3000 feet, so dress more warmly than you think you need to, and consider bringing a blanket, as one of my smart friends did.
The balloon flight itself lasts 45 minutes to an hour, but plan on a two to three hour experience between check in enjoying the after balloon ride festivities, and the trip back to the start.
You arrive well before sunrise, so know that the times for the balloon rides (both sunrise and sunset) vary by time of year to ensure you capture it. When you arrive, you get to witness how the balloon gets inflated – and checked for safety each time.
Our guide was fantastic, and he pointed out all the important sights, from a waterfall I didn’t know existed to wildlife you see as you coast along and more.
I loved floating above the river before we went higher to explore more of the area around Galena. Note that when you land, you don’t get to choose where you land since the balloon is not motorized and depends on the wind.
They aim to land in a farmer’s field where they have an agreement, and a van arrives to pick you up and bring you back to your starting point.
Before the van takes you back, however, you get to enjoy the morning with mimosas in a stainless steel flute provided by the company as you share your memories and receive a signed certificate commemorating your balloon flight.
The Grant Home
With all the history in Galena, Ulysses S. Grant may be the most famous person to come from there. While not born in Galena, he settled there in 1860 and was presented with this house in thanks at the conclusion of the Civil War.
In 1955, the Grant Home was restored to its 1868 state with original furniture, china, and more. It now runs tours of the house every half hour for a suggested donation of $5 per adult and $3 per child.
Located in downtown Galena, it’s an easy walk to 500 Boothillier Street, and you require no reservations.
The house itself isn’t incredibly large, but the history behind it is fascinating, and the docents leading the tours do a fantastic job. I’ve actually taken the tour more than once simple because it is so well done.
For many rooms, you stay outside the room in the hallway with a barrier between you and the room, but you can see everything in it, and the guide provides you with all the information you want to know.
While a young child may not enjoy this, both my teens did and said it was on of their favorite things to do in Galena. The tour itself lasts about a half hour every Wednesday through Sunday throughout the year from 9am to 4:45pm.
The Belvedere Mansion (and gardens) is another tour you can take of a 19th century home. This mansion offers tours from mid-May through mid-November every 15 minutes Monday to Friday 11am to 3:30pm, Saturday 10am to 4:30pm, and Sunday 10am to 3:30pm.
No reservations required. Adults 12 and up cost $14, while kids under 12 are free, though anyone under 18 must be accompanied by an adult.
This mansion is outside the main downtown and is worth driving to versus walking from the downtown area. You can find it at 1008 Park Avenue.
Unlike the Grant House that has been restored to 1868 authenticity, the Belvedere Mansion offers a much more eclectic collection of furniture and art.
The items in the house have been collected over the decades by the owners, and they rotate in and out of the house because there are simply too many to store in the house at one time.
You may see everything from the green curtains from gone with the wind to a piano played by Liberace and so much more.
Fortunately, like the Grant House, you have a tour guide to escort you through the mansion. The tours last about a half hour with a docent sharing all the information they have about the fixtures in each room.
Additionally, once you finish your official tour, you can explore the gardens of the mansion for as long as you wish.
Dowling House is Galena’s oldest house, built in 1826. You can also take a tour of this house (and get a discount if you do both Dowling House and Belvedere Mansion) to learn about the full history of Galena.
Located at 220 Diagonal Street in downtown, it’s more central than Belvedere Mansion.
Like the others, you get a guided tour as part of your admission. This was once a trading post, so it is far smaller with a main first floor room and a kitchen and eating area upstairs.
Here you get a sense of many of the families who lived in Galena at the time and the history they created, not just the Dowlings though much of the focus is on them. As small as it is, this is a fascinating stop not to be missed.
It’s fascinating to see materials from the early 19th century, and here you are allowed to handle some of the antiques. And of course, there is a gift shop next door to make souvenirs easy.
Like so many others, the tour lasts approximately 30 minutes with no reservations required. It is open from 11am to 4pm from mid-March to late October.
Adults 12+ cost $13 and under 12 are free. All under 18 must be accompanied by an adult
One unique note is that the dog of one of the tour guides often accompanies the group. If you have allergies, please be aware.
Galena History Museum
The Galena and U.S. Grant History Museum has grown in the last decade, and they are currently working to open a new museum building they expect to have ready in 2026.
Currently, you can find the museum at 211 South Bench Street in downtown Galena. It’s open daily from 10am to 4:30pm.
In this museum, you can explore at your leisure versus being led on a guided tour. It has over 6,000 square feet of exhibit space.
One of my favorite stops was on the second floor where historical reenactors (who say “me” when talking about Grant!) provided information and answered questions about the president and his wife. It was a neat interactive experience, and the sheer amount of information they had on the Grants was astounding.
You’ll find multiple rooms with multiple displays covering a wide range of subjects from lead mining in the area to Grant’s leather store to steamboats and more. Each display has cards describing what you see, and many have video exhibits providing more detail.
Adults cost $15 to enter, with seniors 65+ $14, and kids 11-18 $12. Those 10 and under enter at no cost, as do museum members.
One of the absolute highlights of my first trip to Galena was visiting the blacksmith shop, which is a part of the history museum complex. Located in a gorgeous red barn at 245 Commerce Street in downtown Galena, you can’t – and don’t want to – miss this.
The down side is that it operates just Friday to Monday from 10am to 4pm from May to October. My last visit was during the week, so I couldn’t take my kids to visit – plan accordingly!
The admission costs $5 per adult or $15 for a family. Those under 10 enter for no charge.
This is a working blacksmith, and volunteers man the forges and make items before your eyes. In fact, what they make goes into the gift shop for visitors to purchase.
The forge itself is filled with tools and materials from the past 100 plus years. You could wander fascinated for hours – or at least I could.
If it isn’t too busy, they blacksmith will actually let kids take a whack at the item he’s making. My kids would have loved that opportunity had it been open when we last visited Galena.
And the nice thing? This is a shop where they talk to you during the demonstration rather than simply having their backs to you while they work. I love that little touch.
P.T. Murphy Magic Theater
I love a good magician show, and I honestly never expected to find one in Galena. However, my friends who have stayed there they past several summers clued me in to the wonder of the P.T. Murphy magic show.
The one hour show is $32.50 per person. No surprise, while there is no age limit, please don’t bring your babies and toddlers to this show.
He offers Friday and Saturday shows in the off season with Wednesday through Saturday shows beginning in mid March. Wednesday to Friday offers 8pm shows, while Saturday has a 3pm matinee show in addition to a 7pm and 9pm show (9pm only in high season).
The small 24 seat theater means you see everything from a prime view. The theater is located in downtown Galena at 204 Hill Street.
The show focuses on sleight of hand with an entertaining repartee throughout and a sense of humor to add to the magic. You will absolutely love this interactive show.
No question, this is one of the best things to do in Galena Illinois, even if you didn’t expect to find it here.
Root Beer Revelry
For those who aren’t here (just for) the history, make sure you stop at Root Beer Revelry. This shop at 228 South Main Street in downtown Galena was absolute heaven for my son.
Though it is not a large shop, it is packed with more root beer and unique sodas than I have ever seen in my life. It is a fantastic and fun place to pick up some unique varieties as you can buy a single bottle rather than a 4 pack or 6 pack like you need to most places.
If you aren’t into root beer (ahem, me), they have plenty of other flavor options from black cherry to orange dreamsicle and so much more. The brands and flavors tend to all be ones you don’t see everywhere else, and it’s just fun.
In fact, you can mix and match your choices to build a discounted pack, and you know we did that. Twice.
The four pack is $11 with a six pack you can mix and match for $15.50, and a case of 24 bottles is $56. Over the holidays, they also offer advent calendars with 24 bottles in themed boxes – a super fun treat.
In addition to bottled root beer and other sodas, they also have six root beers on tap, something I had never seen before.
So yes, please spring for the root beer flight where you can try each of the root beers currently on tap. My son sat at the “bar” and truly enjoyed taste testing and ranking each one.
The root beer flight came on a cute wooden board and was $6.50, definitely worth the price to try all the varieties on tap.
You can also get a root beer float, as well as their merch, but my purist son was solely there for the root beer flight, and he loved it!
Root Beer Revelry is open seven days a week. Monday, Wednesday, and Thursday 10am to 5:30pm, Tuesdays 10am to 5pm, and Friday to Sunday 10am to 6pm.
Shopping Downtown Galena
The entire downtown Galena area is designed for browsing and shopping, which can easily while away an entire afternoon. The shops are pretty much all unique to Galena without chain stores thrust throughout to ruin the ambiance.
You can find anything from antiques to candy stores with unique candies to book stores and more. In fact, there are over 125 shops in the downtown, all in their original buildings.
Some of my favorites include:
- Galena Canning Company for their amazing salsas and jams (and more)
- Carlotta’s Studio for the affordable art, jewelry, and accessories
- Artists’ Annex for the pottery studio where you can watch the artist at work
- At Home in Galena for their locally made soaps, candles, and more
- Celebrity Hats for the unique and oh so fun hats, including one my youngest child purchased there last trip
- Galena Apothecary for the reclaimed pieces as well as the soaps and hand creams and lip balms and more
- Galena Garlic Company for the amazing variety of olive oils and vinegars that I absolutely cannot resist
- Galena’s Kandy Kitchen for the old world homemade chocolates and candy, as well as the penny candy store feel
Though you might not immediately think of Galena as wine country, they have several wineries in the area.
If you want to stay in town, Galena Cellars has a location downtown for tastings (111 N Main Street) as well as their vineyard outside town (4746 N Ford Road). I’ve visited both, and both are worth a trip if you enjoy testing local grown and made wines.
The downtown location has three full floors of seating, giving you plenty of room during the high season. Try to sit outside if the weather cooperates.
At the vineyard, you can taste in the main tasting room, outside, or on the porch of their guest house (which is available to book with both one and two bedroom suites). The views on the porch are so peaceful and where my friends and I happily enjoyed a bottle of wine we purchased from the vineyard.
You can enjoy small bites, cocktails, or wine, which gives something for everyone.
We did a wine flight when we visited, and before we tried our first wine, our sommelier of the day gave us instructions on how to properly sample the wine – swirl, smell, sip, including how to aerate it through your teeth to give it full body as you taste.
The sommeliers at both locations are incredibly knowledgeable and share information about the background of the wines before you taste them or find the perfect bottle to purchase.
You can do a tasting at the bar with six half ounce pours for $8 or a flight of any three wines of your choice with 2 ounce pours each for $12. Galena Cellars also provides a nonalcoholic flight for those who don’t drink (thank you!) for $8.
You can also enjoy wines by the glass ($7-13) or purchase a bottle to enjoy with no cork fee. They will provide the glasses for you to use if you purchase a bottle.
Galena Cellars also offers food from appetizers like wine battered cheese curds to baked brie and fig jam, as well as a variety of flatbreads and even desserts. Everything I tried has been so tasty.
The vineyard is open Friday to Sunday 11am to 5pm in the offseason and every day in high season. Downtown, the tasting room is open Monday to Thursday 11am to 5pm, Friday and Saturday 10am to 8pm, and Sunday 10am to 5pm. The wine and cocktail bar and kitchen have different hours.
Massbach Ridge Winery
Massbach Ridge Winery also has a downtown tasting room (117 N Main Street) and a winery in nearby Elisabeth (8837 S Massbach Road).
Their vineyard lets guests walk through the actual vineyard, which is one of my favorite things to do. Enjoy a glass of wine while you do so to make it even more enjoyable.
Their wine flights offer four one and half ounce pours of wine for $7. This vineyard produces 15 type of wine, so you’re sure to find one to enjoy, and you select your choice from their wine list for the flight.
The vineyard offers amazing views with plenty of covered seating just outside the tasting room for pleasant weather as well as indoor seating. If you have a group of five or more, be sure to reserve your tasting space in advance.
In addition, at the vineyard, they offer bites to accompany the wine, but downtown has no food on site.
They also have an incredibly knowledgeable staff, which only adds to the experience.
The vineyard is open 11am to 5pm seven days a week. In Galena, they have extended hours Sunday to Thursday 11am to 5pm and Saturday and Sunday 11am to 7pm.
Fergedaboutit Vineyard and Winery
Though not technically in Galena, Fergedaboutit Vineyard and Winery is worth a visit in Hanover Illinois, about a 20 miles drive from Galena.
They do not take reservations, so be aware that you may have to wait during popular times. Fergedaboutit grows nine varietals onsite, and they import additional California and Chilean grapes to create a wide variety of styles in both red and white wines.
Like Massbach, you can wander the vineyards with your wine, which is a great way to enjoy a summer or fall afternoon and evening. They employ a fantastic and knowledgeable staff who can answer any questions about your wines.
Enjoy a wine tasting of six one ounce pours for $7. They do limit wine tastings, and they are not available on Saturdays and other high traffic periods.
You can of course also enjoy wines by the glass, including their freezie di vino (a wine slushie) or a wine flight ($12-14, depending on what wine you choose).
This vineyard offers small bites to accompany your wine, which allows you to make more of an afternoon of it. Enjoy a cheese or antipasto platter or a chocolate flight, depending on your mood.
Fergedaboutit is open Wednesday to Friday and Sunday from 11am to 5pm, as well as Saturday from 11am to 6pm from March through mid December.
Rocky Waters Vineyard and Winery
Also in Hanover, Illinois, Rocky Waters Vineyard and Winery is about 14 miles from Galena. Offering 14 wines (with more to come), you will love their tasting room.
All wines are made from grapes grown in their 25 acre vineyard with both red and white varietals available.
Their wine flight provides 7 one ounce samples of wine and 2 one ounce samples of frose for $12. Bonus? For every three bottles of wine you purchase, Rocky Waters credits the cost of one of your wine flights to the third bottle.
They offer pizza and a variety of appetizers from a cheese platter to blueberry baked brie to accompany your wine, as well as cheesecake slices for dessert.
The winery offers both indoor and outdoor seating and plenty of gorgeous views of the vineyard and the surrounding area. With the rolling hills, it’s a peaceful and lovely way to enjoy an afternoon.
In the off season, they are open Monday to Thursday by appointment, as well as Friday and Saturday 10am to 5pm and Sunday 12pm to 4pm. In season, they are open Monday to Saturday 10am to 5pm and Sunday 12pm to 4pm.
Galena Wine Tours
If you prefer to leave the driving to someone else, try a day with Galena Wine Tours. They pick you up from your (nearby) location and take you to various wineries.
Their wine and food tour is $75 per person (cash or Venmo only) and takes you to two wineries in Jo Daviess County where you enjoy their flights of wine, pizza, cheese, and chocolates.
The trip is in a small climate controlled bus and includes the food and tasting fees, as well as bottled water. The three hour tour heads begins at 11am seven days a week.
The wine, food, and brew tour is $85 per person (also cash or Venmo) and offers an additional stop at a brewing company for a beer or glass of wine in addition to pretzels. The additional stop makes this a four hour tour.
Tours start at 2pm on Thursdays and Fridays, 11am on Saturdays and Sundays, and a second option of 2pm on Saturdays.
Both tours require a minimum of eight people to run, and if you have twelve or more, you can have a private tour. Because it involves pickup from your lodgings, pickup times vary, and they will let you know what time to expect them.
Chestnut Mountain Activities
I have visited Chestnut Mountain both on my own and as part of press trips in both summer and winter. No matter the season, Chestnut Mountain is worth a visit.
Chestnut Mountain is located about ten miles from downtown Galena, though still in Galena itself. They have a hotel onsite with inexpensive and serviceable rooms that are nothing fancy but always clean.
They also have two restaurants on site, so you once you get settled, you don’t have to venture out to find somewhere to eat. The food is pretty good and not outrageously priced.
If you visit in summer, you have to do the Apline slides that run down the ski runs in concrete channels. They also have segway tours, mini golf, bike rentals, dics golf, a zipline, and more. You can learn everything you want to know in my article about Chestnut Mountain summer activities.
In winter – no surprise – you can ski or snowboard, but you’ll want to enjoy the indoor pool and hot tubs, as well to relax apres ski. They have great instructors for lessons at a variety of levels, as well as everything from a bunny hill to black diamond runs and trails, plus a seven acre terrain park.
You can learn everything you need to know about enjoying Chestnut Mountain for skiing and snowboarding in my Chestnut Mountain winter activities article. I don’t care what season it is though, Chestnut mountain has some of the most fun things to do in Galena Illinois all in one place.
And of course (pun intended), there are golf courses aplenty in the Galena area. Eagle Ridge has multiple courses available to suit your needs.
Note that Eagle Ridge adheres to stringent golf etiquette, so ensure you come dressed in proper attire and know that you cannot bring your own beverages on the course.
If you are staying at Eagle Ridge Resort and Spa can reserve tee times at any point once you have your reservation confirmation number. If you are a golf member or guest of a golf member, you can make reservations 14 days in advance, while others can reserve seven days ahead.
Eagle Ridge has four different courses to meet your needs. The par 72 General is the most well known and traditional of the courses.
The North Course is also a par 72 and includes elevated tee boxes significant elevation change from tee box to green on many holes.
The South Course has a lot of water nearby, with 11 of the 18 holes playing near or through streams. It is a shorter course but more challenging, requiring greater accuracy and shot making skills.
The East Course is a nine hole par 34 course, perfect for beginners or juniors. In addition to traditional golf, this course offers foot golf as an additional option for younger golfers and beginners who may not be up to a traditional game.
Pricing varies based on age, time of day, and membership status as well as which course you choose. They range from $16 for 17 and under to play the east course in the off season to $140 for the public on The General May through mid October.
In addition, there are stay and play packages with Eagle Ridge Resort and Spa for multiple rounds of golf, free range balls, included breakfast, and more. Check out their golf packages for current rates and availability.
There are also pros to provide lessons and a golf simulator to help you improve your game.