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Galena: Off The Tourist Track & Under The Radar

Steeped in history, Galena has long been a favorite Midwest weekend travel destination. And why not? Tucked away in the far northwest corner of Illinois, Galena offers numerous fine dining options, boutique shopping, plentiful lodging, and a bevvy of attractions …

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Visit Historic Galena, illinois

A four season getaway, this charming town of 3,500 is located along Route 20, a picturesque drive from locales in Illinois or neighboring Wisconsin and Iowa. A favorite of Chicagoans, Galena has transformed from a sleepy weekend antique shopping community to a highly popular choice for travelers of all ages and demographics …

If you’ve visited Galena before, you’ve undoubtedly strolled along Main Street, affectionately known as “The Miracle Half Mile”. Main Street is the heart of Galena – it’s where you’ll find most of the shops and restaurants, and it’s what most people talk about when they reflect on visits here …

Galena’s Best Updated Deals – See Them Here

This travelogue, though, digs a little deeper …




What follows is the crux of MidwestRiverCities.com – we wander off the tourist track, embrace the local, and highlight places you won’t often hear about …

And so, here’s a list of 15+ somewhat “under the radar” Galena destinations you’ll want to add to your itinerary. They underscore what you’ll come to know about this Illinois river city … there’s more here than meets the eye!

Galena’s River

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Galena River From The Grant Park Foot Bridge

Galena is very near the Mississippi River, but not beside it … the center of town is actually about six miles from the great river. However, Galena is indeed a river city – the aptly named Galena River cuts right through the heart of town …

Not a large river but majestic in its own way, the Galena River begins about 50 miles north of town in southern Wisconsin. From there, it meanders through the higher terrain of southwestern Wisconsin before forging its way through Galena.




It empties into the Mississippi south of Galena, serving as a popular choice for kayakers. There’s a convenient launch into the river in Depot Park, on the east bank just across from busy Main Street. More about Depot Park in a few minutes …

Get Up Close & Personal With The River

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Pick Up The Galena River Trail Here …

If a little fresh air and exercise sounds like the perfect antidote to shopping and dining, head over to Depot Park on the east side of the river. There, underneath the Rt. 20 bridge, you’ll find the trail head of the Galena River Trail. This 5+ mile trail follows the river’s path near to where it empties into the Mississippi River …

Free to access and enjoy, this crushed gravel trail is perfect for walkers, hikers, joggers, and bikers. At several points, you’ll find yourself mere feet from the Galena River’s banks. During winter, cross country skiers frequent the trail, and bird watchers delight in the many sights and sounds through the wooded terrain …

The Trail is divided into several segments, and extends north along the river through Depot Park, Grant Park, and beyond. There’s even several exercise stations along the way. Natural Galena at its finest!

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Fever River Outfitters, Galena

Want to get in the river? Check out Fever River Outfitters, located on the south end of Main Street (just north of Route 20). This friendly outpost will set you up with whatever you need for the day, including rentals of canoes, kayaks, bikes, scooters, cross country gear, and more …

The knowledgeable staff is happy to recommend area spots to hike, bike, paddle, or ski and they’re the go to place in Galena for active outdoor group events. Even if you have your own outdoor gear, stop in to see their selection of apparel, footwear, and other useful equipment.

Who Doesn’t Love A Good Bakery?

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Stop In For Breads, Muffins, Pies, & More

With every river city or town we spotlight on Midwest River Cities, we always seek out a good bakery. In Galena, that’s Klein’s Market Bakery, located at 118 S. Main.

Known for their many varieties of freshly baked bread (Insider Tip: try the pumpkin bread), this bakery also creates a tantalizing selection of cakes, pies, cookies, and more.

For a yummy inexpensive breakfast, stop in for a cinnamon roll and cup of hot chocolate (of course there’s plenty of coffee waiting for you too) …

The Oldest Bar In Town

If you value a sense of history, you’ll love Galena. History is everywhere you turn, from the historic architecture to the specter of Ulysses S. Grant. Grant, our 18th president, was a Civil War hero who called Galena home before and after the war …

So proud was Galena of Grant’s Civil War triumphs, the town bestowed a stately brick home to the General and his family on a hill just east of downtown. That home still stands, and is open for tours for a nominal fee.

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Grant’s Bivouac: Galena’s Oldest Bar

Legend has often told the tale of Grant’s fondness for drink. Therefore, it’s appropriate we spotlight Galena’s oldest bar which pays homage to the town’s most famous historical resident.

It’s the VFW at 100 S. Main Street, which is dubbed Grant’s Bivouac. Open to the public, this branch of the VFW has been open since at least the 1930’s, although exact dates may be lost to history. The VFW is a no frills, friendly local place absent of any pretense and welcoming to all walks of visitors. It’s a great place to settle in for a cold one if you need a break from shopping (or someone who likes to shop!).

General Grant’s Personal Memoirs – Click Here

Farther up Main Street are two other historic restaurant / bars of note, the Log Cabin Restaurant and The Gold Room …

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Galena’s iconic Log Cabin Steakhouse

Open since the mid 1930’s The Log Cabin is a long time local favorite that is is now officially called Log Cabin Steakhouse. Open daily at 4 p.m., this is the place to go for a great steak or specialty Greek style appetizers like Flaming Saganaki and Greek Feta with Kalamata Olives …

On weekends, Log Cabin Steakhouse hosts Galena’s favorite piano bar and the prime rib is a long time choice of those in the know …

Insider Tip: The filet mignons, lamb chops, and porterhouse steaks rival those at any big city steakhouse. Meat is sourced from Chicago’s famed Allen Brothers meat company. A dinner here is a bit of a splurge but well worth it!

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Great Local Bar On Main Street, Galena

Finally, at 249 N. Main (at Franklin), you’ll find the newly remodeled and reopened Gold Room, a friendly conversational “come as you are” tavern. Where the locals go in Galena, the Gold Room was recently given a fresh start with new ownership and a sprucing up.

Stop in here to recharge and refresh after strolling the east side of Main, before you cross the street and explore the other side …

Galena Green: Visiting The Parks

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The Boat Launch At Depot Park

Depot Park, as mentioned above, is situated on the east bank of the Galena River. The centerpiece of the park is the old railroad depot which retains the charm and character of the days when Galena was a prominent railroad center …

The park offers plenty of parking and ten acres to spread out and enjoy a picnic with great views of the downtown area across the river. It’s also where you can launch into the river with your kayak or canoe, and access to the Galena River Trail is at the park’s southern end …

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A Tranquil Oasis In Galena

Just to the north of Depot Park is expansive Grant Park, where a statue of Ulysses S. Grant overlooks the sloping grounds. A highlight is an old Civil War cannon located near the gazebo, as well as the foot bridge offering convenient access across the river to downtown …

Both parks are easy to find just off of Route 20 and they’re excellent places to walk, unwind, walk your dog, or just enjoy nature …

Learn more about these and other Galena parks here

Budget Friendly Galena Shopping

There’s a common misconception that a weekend of Galena shopping means bringing a stuffed wallet. For those of us on a budget, here’s five local shops where you’ll find eclectic, unique goods at easy on the wallet prices …

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Savvy Scavengers – Galena

Two of our favorites are located right around the corner from one another …

First is Savvy Scavengers, a women’s clothing boutique specializing in overstock fashions, purses, shoes, jewelry and much more, Savvy Scavengers is a welcome addition to the Galena scene. Step inside and you’ll find a boutique atmosphere offering an ever changing selection at prices just a fraction of retail …

Insider Tip: If you’re traveling to Galena from the Chicago area, there’s a Savvy Scavengers branch store in the small town of Stockton, west of Freeport and Rockford. It’s about 3 blocks south of Rt. 20 on Main Street (Rt. 78), on the north edge of Stockton’s downtown area …

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Great Women’s Fashion Deals!

Just around the corner from Savvy Scavengers on Franklin Street is another can’t miss stop for women’s fashion. It’s a brand new shop called Galena Resale and this store will change your view of resale shops forever …

Galena Resale is not a consignment shop … owner Lauren Knepp seeks out top brand names like Banana Republic, Ann Taylor, Chico’s, and Ralph Lauren and obtains the fashions in all range of sizes. Each item is carefully washed or dry cleaned and displayed according to size and color. Stock is frequently rotated and prices are unbeatable!

Who said there’s no bargains in Galena any more??

Galena For Less Than You’d Expect: Click Here

For local art and unique home decor, we like Outside The Lines Art Gallery, located in the heart of town at 101 S. Main. Here you’ll find local art and pottery, hand crafted jewelry, sculpture, functional furniture, and home decor you won’t find elsewhere. A can’t miss stop on your Galena visit, Outside The Lines always offers something new and different for your home …

insider Tip: Outside The Lines has a second location in Dubuque, another historic river city just 15 minutes west of Galena on Route 20. They’re located in the 4th and Bluff shopping district, in the shadow of Dubuque’s famed Fenelon Place Elevator …

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Local Authors Abound At Book World!

If you’re a reader and you appreciate local authors, stop in at Book World, just south of Outside The Lines at 300 S. Main. Featuring a relaxed, welcoming atmosphere, Book World showcases a wide selection of books, gift items, and much more. This is where you’ll find books by local authors, like the title shown in the photo … there’s nothing quite like a local book store!

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Rustic River Finds, Main St. Galena

Another shop you’ll want to know about is located at 109 N. Main … it’s called Rustic River Finds and what makes it special is all the jewelry here is hand crafted. Nothing is mass produced, quantities are limited, and you’re sure to find a piece perfectly suited to your style and persona …

The store’s stock changes according to season, so what you’ll see in the winter will be gone when the warmer weather arrives. If you can’t make it to Galena, you can also shop online at the Rustic River Finds website, linked above …

Grab A Bite Off The Main Street Hustle & Bustle

The one thing you won’t have any trouble finding in Galena is a place to eat. From breakfast options to stylish desserts and everything in between, Main Street has you covered …

However, if you’re looking for something a little quieter and maybe a little more “local”, these two options may well be right up your alley …

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Otto’s Place – Galena

Located on the east side of the river adjacent to Depot Park, Otto’s Place is a bright, friendly option serving breakfast and lunch. If you go in and ask for Otto though, there isn’t one. Otto refers to Otto Stillman, the original builder of the building which currently houses the restaurant. Dating back to 1899, the historic building has housed a restaurant, bakery, grocery store, antique shop, and now a restaurant again …

Otto’s places an emphasis on healthy home cooking featuring local ingredients served in a relaxed, cheerful setting. They serve beer, wine, spirits, and homemade desserts … it’s an excellent option after touring the Grant home just up the street or visiting the nearby parks.

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Dillon’s Pizza – Franklin Street

About six blocks up on Franklin Street from Galena Resale, you’ll find one of Galena’s only local pubs. It’s Dillon’s Pizza. Aptly described as a local bar and grill, the menu features pizza, chili dogs, grilled sandwiches, hamburgers, and the like. Beer is served (bottles only when we stopped in) and the atmosphere is low key and friendly …

If you’re wanting to explore your options off of Main Street, Dillon’s is an excellent choice!

Summary & Thank You

Galena is the kind of place everyone needs to visit at least once. The only problem with that statement is that Galena’s many charms will draw you back again and again …

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The Galena River Trail

Over the past few decades, Galena has transformed itself from sleepy to trendy. That’s not necessarily a bad thing … rather, it’s reflective of changing tastes and changing times. You don’t have to look too hard to find local independent gems though … these 15+ are just a start, and we plan on adding more over the coming months …

Galena is a small town full of surprises, even for visitors who’ve been coming here for years. Retail options are ever changing, with impressive new businesses and entrepreneurial ventures taking hold. Yet the town retains its natural historic charm … and we suspect it always will.

Get The Latest Discounts In & Around Galena – Click Here!

Add Galena to your weekend to do list, or better still, visit during the week when there’s a bit more room to explore. And remember, Galena is within a short drive of a few other Midwest river cities … Dubuque is only a few minutes west on Route 20 and Rockford and Beloit are only an hour away.

Enjoy your visit to Galena and let us know what you think by commenting below!

A special thank you goes out to Rose Noble of VisitGalena.org for her assistance in helping to plan our visit …

    1 Comment

  1. Wandering off the Galena tourist track was so much fun! There are all kinds of cool local businesses to explore … what are some of your favorites?

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